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1. Investigation of second-order nonlinear optical responses in a series of V-shaped binuclear platinum(<scp>ii</scp>) complexes

Author: Sébastien Gauthier, Denis Jacquemin, Françoise Robin-le Guen, Elsa Caytan, Sylvain Achelle, Raphaël J. Durand, Alberto Barsella, Nicolas Le Poul, Patricia Guevara Level, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Chimie, Electrochimie Moléculaires et Chimie Analytique (CEMCA), Université de Brest (UBO)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Ministère de l'Enseignement supérieur, de la Recherche et de l'Innovation, Centre National de la Recherche Scientifique, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), and Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, Series (mathematics), Pyrimidine, Ligand, chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Electrochemistry, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Crystallography, chemistry, [CHIM]Chemical Sciences, Order (group theory), Density functional theory, 0210 nano-technology, Platinum, Malononitrile
Abstract: International audience; A series of four D-(π-Pt-π-A)2 new V-shaped binuclear platinum(ii) complexes bearing a diphenylpyranylidene ligand as a pro-aromatic donor group (D) and various electron-attracting groups (A) separated by platinum bis-acetylide fragments have been synthesized, characterized and studied for their electrochemical, photophysical and second-order nonlinear optical (NLO) properties. The nonlinear optical properties of these complexes have been determined by using the Electric-Field-Induced Second Harmonic (EFISH) generation technique, and their optical properties have been rationalized by Time-Dependent Density Functional Theory (TD-DFT) calculations relying on a range-separated hybrid. All complexes display positive μβ0 values. In addition, the second-order NLO responses of the complexes could be easily modulated by incorporating various end-capped electron-attracting groups, namely malononitrile, indane-1,3-dione, pyrimidine and pyrimidinium. Remarkably, complex 7 bearing a pyrimidinium fragment displays the highest μβ0 value among all the complexes of this series. Its NLO response is twice as high as that of the mononuclear analogue complex RD2, which has been confirmed both experimentally and theoretically.
Published: 2021
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2. V-Shaped Methylpyrimidinium Chromophores for Nonlinear Optics

Author: Alberto Barsella, Filip Bureš, Françoise Robin-le Guen, Sylvain Achelle, Michaela Fecková, Egor V. Verbitskiy, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Ural Federal University [Ekaterinburg] (UrFU), Institute of Organic Chemistry and Technology [University of Pardubice], University of Pardubice, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Russian Foundation for Basic Research. Grant Number: 18-29-23045, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), and Jonchère, Laurent
Subjects: Materials science, pyrimidines, donor-acceptor systems, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Electric field, [CHIM] Chemical Sciences, PYRIMIDINES, SECOND-ORDER NONLINEAR OPTICS, Figure of merit, chromophores, [CHIM]Chemical Sciences, DONOR-ACCEPTOR SYSTEMS, photophysics, Chloroform, 010405 organic chemistry, Nonlinear optics, Regioselectivity, Second-harmonic generation, General Chemistry, Chromophore, 0104 chemical sciences, Crystallography, Dipole, chemistry, CHROMOPHORES, second-order nonlinear optics, PHOTOPHYSICS
Abstract: A series of four V-shaped methylpyrimidinium salts bearing diphenylamino-electron-donating groups appended at various pyrimidine positions were designed. These chromophores were obtained by regioselective N(1) monomethylation by methyl methanesulfonate of the pyrimidine core. Linear optical properties were studied experimentally and electronic properties were further completed by (TD)-DFT calculations. The second-order nonlinear optical (NLO) properties were also studied using electric field induced second harmonic generation (EFISH) method in chloroform, and all pyrimidinium salts exhibited μβ0>1000×10−48 esu. The 2,4-disubstituted pyrimidinium core is preferred over 4,6-disubstitution as it enhances the NLO response and increases the dipole moment. (E,E)-2,4-Bis[4-(diphenylamino)styryl]-1-methylpyrimidin-1-ium methanesulfonate appears to be the best NLO-phore in chloroform in the series (μβ0=2500×10−48 esu) and a figure of merit μβ0/MW=3.4 10−48 esu mol g−1. © 2021 Wiley-VCH GmbH VEV is grateful for the financial support for the synthetic part related to compound 3 from the Russian Foundation for Basic Research (Research Project No. 18-29-23045 mk). MF acknowledges the Région Bretagne, France for her Ph.D. funding (HOLED project).
Published: 2021
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3. Amino-substituted-1,1-dicyano-2,4-diaryl-1,3-butadiene chromophores: Synthesis and photophysical properties

Author: Alberto Barsella, Zeynel Seferoğlu, Mohamed Hisham Yahya, Sylvain Achelle, Nurgül Seferoğlu, Gazi University, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), and Jonchère, Laurent
Subjects: Chemical substance, Triphenylamine, 02 engineering and technology, NIR emission, 010402 general chemistry, DFT calculations, 01 natural sciences, Analytical Chemistry, chemistry.chemical_compound, Nonlinear optical, Computational chemistry, Electric field, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, Instrumentation, Spectroscopy, Push–pull, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Allylidenemalononitrile, 1,3-Butadiene, Second-harmonic generation, Chromophore, [CHIM.ORGA] Chemical Sciences/Organic chemistry, 021001 nanoscience & nanotechnology, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Intramolecular charge transfer (ICT), chemistry, 0210 nano-technology, Science, technology and society
Abstract: International audience; A series of D-π-A chromophores based on allylidenemalononitrile electron-withdrawing group was designed. The influence of the amino-electron-donating group on the photophysical properties was studied. These compounds, highly thermally stable, exhibit orange-red emission in solution and in solid state. The experimental results have been rationalized by theoretical DFT calculations. The second order nonlinear optical properties were also studied using the electric field induced second harmonic generation (EFISH) method.
Published: 2021
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4. Synthesis and investigation of photophysical, NLO and thermal properties of D-pi-A-pi-D dyes

Author: Zeynel Seferoğlu, Deniz Çakmaz, Hülya Şenöz, Arda Özarslan, Alberto Barsella, Nurgül Seferoğlu, Fatma Erol, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS)
Subjects: Thermogravimetric analysis, 010405 organic chemistry, Chemistry, Carbazole, Organic Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Acceptor, 0104 chemical sciences, Analytical Chemistry, Inorganic Chemistry, chemistry.chemical_compound, Bathochromic shift, Moiety, Thermal stability, Absorption (chemistry), [CHIM.OTHE]Chemical Sciences/Other, Spectroscopy, Derivative (chemistry)
Abstract: A novel coumarin-thiophene based dyes containing azo and dimethine bridges with D-pi-A-pi-D system were synthesized and investigated their photophysical, nonlinear optical (NLO) and thermal properties. The dyes were characterized by FT-IR, H-1-NMR, C-13-NMR and HRMS. The dyes include dicyanomethylene group as acceptor and different para-substituted alkylamines and carbazole as donor and chlorophenyl as weak acceptor. The photophysical properties of dyes were examined in various solvents with different polarities and they showed absorption in the visible region. The significant bathochromic shifts were observed in the absorption maxima with increasing the electron-donating property of substituents. The second order NLO responses of the compounds are measured by the electric field induced second harmonic (EFISH) generation method and the compounds bearing dialkylamino donor in phenyl moiety were obtained as the larger mu beta values 1300 x 10(-48) esu, 1850 x 10(-48) esu, respectively, than unsubstituted derivative in phenyl ring mu beta value 350 x 10(-48) esu. The structural and electronic properties of the compounds as well as their NLO properties were studied using DFT calculation. The thermal stabilities obtaining with thermogravimetric analysis (TGA) showed that the dyes have generally a good thermal stability up to 250 degrees C. (C) 2020 Elsevier B.V. All rights reserved.
Published: 2021
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5. New styryl based organic chromophores including free amino and azomethine groups: Syntheses, photophysical, NLO and thermal properties

Author: Nurgül Seferoğlu, Deniz Çakmaz, Zeynel Seferoğlu, Anka Utama Putra, and Alberto Barsella
Subjects: chemistry.chemical_compound, Schiff base, Chemistry, Physical organic chemistry, Protonation, Thermal stability, Chromophore, Solvent effects, Absorption (chemistry), Photochemistry, Acceptor
Abstract: In this manuscript, we have successfully synthesized and characterized a new series of styryl based push-pull dyes containing free amino group and their Schiff bases derivatives in which dicyanomethylene was used as the acceptor group and different para-substituted alkylamines as the donor groups and 2-pyridyl as proton sensitive group. All compounds showed absorption in the visible region and green-red emission with low quantum yields. The photophysical properties were examined in various solvents with different polarities. The absorption and emission maxima were shifted bathocromically by increasing solvents polarity however, there was no regular correlation with polarity parameter. Significant red shifts were observed in the absorption and fluorescence emission maxima on increasing the electron-donating ability of the substituents. The observed color changes were photographed naked eyes and under illuminating UV-lamp. The pH sensitive properties of newly prepared Schiff bases against TBAOH were examined inside DMSO, furthermore their reserve protonation were also investigated using TFA. The structural and electronic properties of all newly synthesized compounds were studied using DFT calculation. In addition, NLO property of compounds were investigated by DFT. For determination thermal properties of all compounds were investigated and they showed good thermal stability up to 250 oC by TGA analyses under inert atmosphere. Our results indicate that the styryl based new push-pull dyes are promising candidate materials for NLO and pH applications.
Published: 2020
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6. Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Author: Nurgül Seferoğlu, Deniz Çakmaz, Alberto Barsella, Zeynel Seferoğlu, Anka Utama Putra, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS)
Subjects: Substituent, Protonation, DFT calculations, NLO, 010402 general chemistry, Photochemistry, 01 natural sciences, Full Research Paper, lcsh:QD241-441, Schiff base, chemistry.chemical_compound, Deprotonation, lcsh:Organic chemistry, Bathochromic shift, Moiety, lcsh:Science, Julolidine, solvent effect, 010405 organic chemistry, Chemistry, Organic Chemistry, styryl dyes, Chromophore, pH sensitive dyes, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, lcsh:Q
Abstract: Herein we report the synthesis and characterization of a new series of styryl-based push-pull dyes containing a free amino group and their Schiff base derivatives. The dyes include the dicyanomethylene group as an acceptor and different para-substituted alkylamines as donors. Morever as a proton-sensitive group a pyridin-2-yl substituent was attached to the para-position of the phenyl moiety in both series of compounds. The photophysical properties of the dyes were examined in various solvents with different polarities and showed absorption in the visible region and green-red emission with low quantum yields. The absorption and the emission maxima were shifted bathocromically by increasing the solvent’s polarity. However, there was no correlation with the polarity parameters of the solvents. The pH-sensitive properties of all prepared Schiff bases were examined against TBAOH in DMSO, via deprotonation of the OH group in the salicylidene moiety and their reverse protonation was also investigated using TFA. The Schiff bases exhibited a bathochromic shift upon the addition of TBAOH to their solutions in DMSO. Therefore, they showed potential to be utilized as colorimetric and luminescence pH sensors. The second-order nonlinear optical (NLO) responses of the dyes were measured by the electric field-induced second harmonic (EFISH) generation method. The highest μβ values were obtained for the dyes bearing the julolidine donor as 1430 × 10−48 esu (for free amino derivative) and 1950 × 10−48 esu (for Schiff base derivative), respectively. The structural and electronic properties of the dyes as well as their NLO properties were further studied using DFT calculations. The thermal stabilities of all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C.
Published: 2020
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7. Push–pull D–π-Ru–π-A chromophores: synthesis and electrochemical, photophysical and second-order nonlinear optical properties

Author: Sébastien Gauthier, Françoise Robin-le Guen, Nicolas Le Poul, Samia Kahlal, Thomas Groizard, Alberto Barsella, Jean-Yves Saillard, Raphaël J. Durand, Sylvain Achelle, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Chimie, Electrochimie Moléculaires et Chimie Analytique (CEMCA), Université de Brest (UBO)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: Materials science, Pyrimidine, chemistry.chemical_element, NLO, 010402 general chemistry, Electrochemistry, 01 natural sciences, Redox, Inorganic Chemistry, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, ruthenium complexes, [CHIM]Chemical Sciences, [CHIM.COOR]Chemical Sciences/Coordination chemistry, ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Second-harmonic generation, Non-linear optic, Chromophore, pyranylidene ligand, 0104 chemical sciences, Ruthenium, Crystallography, Dipole, chemistry, Intramolecular force
Abstract: The present work describes the one-pot synthesis and electrochemical, photophysical and second-order nonlinear optical (NLO) properties of a series of dipolar π-delocalized Ru(II) dialkynyl complexes. The eight new asymmetrical D–π-Ru–π-A push–pull chromophores incorporate pyranylidene ligands as pro-aromatic donor groups (D) and formaldehyde, indane-1,3-dione, pyrimidine or pyrimidinium as electron-attracting groups (A) separated by ruthenium bis-acetylide fragments and π-conjugated linkers. The second-order nonlinear optical (NLO) properties of all eight complexes were determined by the Electric-Field-Induced Second Harmonic generation (EFISH) technique (operating at 1907 nm), and were compared to those of their purely organic analogs. All investigated compounds (organic and organometallic) exhibited positive μβ values, which dramatically increased for the complexes due to the presence of ruthenium in the π-conjugated core. The second-order NLO response could also be easily modulated by changing the nature of alkynyl substituents. The most promising ruthenium complexes 7 and 8 of the series with the pyrimidinium fragment displayed μβ values of 14 000 × 10−48 esu. The effect of structural modifications on the redox and spectroscopic properties of the complexes was also studied. The intramolecular charge transfer (ICT) occurring through the ruthenium center of the push–pull σ-dialkynyl complexes was investigated by combining experimental and theoretical data.
Published: 2018
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8. Electron-Withdrawing Substituted Quinazoline Push-Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second-Order Nonlinear Optical Properties

Author: Sylvain Achelle, Filip Bureš, Pascal Le Poul, Galina N. Lipunova, Tatiana N. Moshkina, Emiliya V. Nosova, Françoise Robin-le Guen, Alberto Barsella, Valery N. Charushin, Oldřich Pytela, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Ural Federal University [Ekaterinburg] (UrFU), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), University of Pardubice, Russian Academy of Sciences [Moscow] (RAS), Russian Foundation for Basic Research (RFBR) [18-03-00112, 19-33-90014], Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Substituent, Second-harmonic generation, Quinazoline, Chromophore, 010402 general chemistry, Photochemistry, 01 natural sciences, Fluorescence, Push-pull derivatives, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Nonlinear chromophores, chemistry, Polar effect, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, Cyclic voltammetry, Intramolecular charge transfer, Luminescence
Abstract: International audience; A series of chromophores bearing 4-cyanoquinazoline, 2-(4-cyanophenyl)quinazoline or 2-(4-trifluorophenyl)quinazoline electron-acceptor (A) and 5-(4-aminophenyl)thiophen-2-yl or 4-aminophenyl electron-donor (D) units has been designed. The influence of the electron-withdrawing substituent on the pyrimidine core as well as the nature of the amino electron donating group has been studied by cyclic voltammetry, UV/Vis and emission spectroscopy. Whereas 2-(4-cyanophenyl)quinazoline and 2-(4-trifluorophenyl)quinazoline derivatives are highly luminescent in chloroform solution, 4-cyanoquinazolines are poorly emissive. Interestingly all compounds are luminescent in the solid state with the emission ranging from blue to red. The second order nonlinear optical properties were studied using electric field induced second harmonic generation (EFISH) method. Quantum-chemical calculations corroborate the aforementioned experimental results.
Published: 2020
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9. Synthesis, photophysical and nonlinear optical properties of [1,2,5]oxadiazolo[3,4-b]pyrazine-based linear push-pull systems

Author: Valery N. Charushin, Oleg N. Chupakhin, Filip Bureš, Yuriy A. Kvashnin, Sylvain Achelle, Gennady L. Rusinov, Pascal Le Poul, Egor V. Verbitskiy, Alberto Barsella, Françoise Robin-le Guen, Ural Federal University [Ekaterinburg] (UrFU), Ural Branch of Russian Academy of Sciences (UB RAS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculty of Chemical Technology [University of Pardubice], University of Pardubice, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Russian Foundation for Basic Research: 18-29-23045, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: Pyrazine, NONLINEAR OPTIC, General Chemical Engineering, DONOR–ACCEPTOR SYSTEMS, General Physics and Astronomy, 02 engineering and technology, 010402 general chemistry, intramolecular charge transfer, 01 natural sciences, chemistry.chemical_compound, INTRAMOLECULAR CHARGE TRANSFER, Electric field, [CHIM]Chemical Sciences, Order (group theory), Emission spectrum, FLUORESCENCE, NITROGEN HETEROCYCLES, donor–acceptor systems, Chemistry, Second-harmonic generation, General Chemistry, Chromophore, 021001 nanoscience & nanotechnology, Fluorescence, 0104 chemical sciences, nonlinear optic, Physical chemistry, fluorescence, nitrogen heterocycles, Cyclic voltammetry, 0210 nano-technology
Abstract: A series of D-π-A chromophores based on [1,2,5]oxadiazolo[3,4-b]pyrazine electron-withdrawing group has been designed. The influence of the π-conjugated linker (1,4-phenylene and 2,5-thienylene) and the amino-electron-donating group (diphenylamino and carbazol-9-yl) was studied by cyclic voltammetry, UV-Vis and emission spectroscopy. The second order nonlinear optical properties were also studied using the electric field induced second harmonic generation (EFISH) method. The experimental results have been rationalized by theoretical DFT calculations. © 2020 Elsevier B.V. VEV is grateful to the financial support for the synthetic part from the Russian Foundation for Basic Research (Research Project No. 18-29-23045 mk).
Published: 2021
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10. Indole based push-pull dyes bearing azo and dimethine: Synthesis, spectroscopic, NLO, anion affinity properties and thermal characterization

Author: Alberto Barsella, Burcu Aydıner, Nurgül Seferoğlu, Zeynel Seferoğlu, Mohamed Hisham Yahya, Ebru Aktan, Ergin Keleş, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS)
Subjects: Indole test, Thermogravimetric analysis, Aqueous solution, Chemistry, General Chemical Engineering, General Physics and Astronomy, 02 engineering and technology, General Chemistry, Chromophore, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Proton NMR, Titration, Thermal stability, 0210 nano-technology, Selectivity
Abstract: A series of novel indole based push-pull dyes bearing azo and dimethine chromophores in same structure were synthesized and characterized by Fourier Transform Infrared (FT-IR), 1H/13C nuclear magnetic resonance (NMR), and mass spectrometry. The photophysical properties of the dyes were determined in three various solvents in UV-Vis spectra and theoretical studies. Their chemosensor and nonlinear optic (NLO) properties were also investigated. Anion selectivity and sensitivities of dyes were studied with some selected anions in ACN and interaction mechanisms were confirmed by spectrophotometric and 1H NMR titration techniques. While in the organic solvents such as DMSO and ACN the dyes showed affinity to F-, AcO-, CN-, and H2PO4- and they showed selective behaviour only to CN- in partial aqueous solution. The thermal stabilities obtaining with thermogravimetric analysis (TGA) showed that the dyes have a good thermal stability up to around 300 °C.
Published: 2020
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11. Electronic energy and electron transfer processes in photoexcited donor–acceptor dyad and triad molecular systems based on triphenylene and perylene diimide units

Author: Olivier Crégut, Yiming Xiao, Kwang Jin Lee, Alberto Barsella, Eunsun Kim, J. H. Woo, Fabrice Mathevet, Xiaolu Su, A. J. Attias, Loic Mager, Frédéric Fages, Anthony D'Aléo, J. W. Wu, Leszek Mateusz Mazur, Jean-Charles Ribierre, Jodrell Bank Centre for Astrophysics, University of Manchester [Manchester], CNRS-Ewha International Research Center, Laboratoire d'analyse et modélisation de systèmes pour l'aide à la décision (LAMSADE), Université Paris Dauphine-PSL, Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS), Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Chimie des polymères (LCP), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Quenching (fluorescence), General Physics and Astronomy, Triphenylene, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Acceptor, 0104 chemical sciences, Electron transfer, chemistry.chemical_compound, chemistry, Diimide, Ultrafast laser spectroscopy, [CHIM]Chemical Sciences, Molecule, Physical and Theoretical Chemistry, 0210 nano-technology, Perylene
Abstract: International audience; We investigate the photophysical properties of organic donor-acceptor dyad and triad molecular systems based on triphenylene and perylene diimide units linked by a non-conjugated flexible bridge in solution using complementary optical spectroscopy techniques. When these molecules are diluted in dichloromethane solution, energy transfer from the triphenylene to the perylene diimide excited moieties is evidenced by time-resolved fluorescence measurements resulting in a quenching of the emission from the triphenylene moieties. Simultaneously, another quenching process that affects the emission from both donor and acceptor units is observed. Solution ultrafast transient absorption measurements provide evidence of photo-induced charge transfer from either the donor or the acceptor depending upon the excitation. Overall, the analysis of the detailed time-resolved spectroscopic measurements carried out in the dyad and triad systems as well as in the triphenylene and perylene diimide units alone provides useful information both to better understand the relations between energy and charge transfer processes with molecular structures, and for the design of future functional dyad and triad architectures based on donor and acceptor moieties for organic optoelectronic applications.
Published: 2016
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12. T-Shaped (Donor-π-)2Acceptor-π-Donor Push-Pull Systems Based on Indan-1,3-dione

Author: Oldřich Pytela, Loic Mager, Zdeňka Růžičková, Filip Bureš, Alberto Barsella, Tomáš Mikysek, Milan Klikar, and Parmeshwar Solanke
Subjects: Absorption spectroscopy, Chemistry, Organic Chemistry, Chromophore, Ring (chemistry), Electrochemistry, Acceptor, Crystallography, chemistry.chemical_compound, Computational chemistry, Thiophene, Molecule, Figure of merit, Physical and Theoretical Chemistry
Abstract: Sixteen model (donor–π–)2acceptor–π–donor [(D–π–)2A–π–D] molecules with an extraordinary T-shaped arrangement were designed and synthesized. Indan-1,3-dione was employed as a central acceptor with electron donors linked at the C-2, C-4, and C-7 positions. These push–pull molecules represent a first systematic modification of an indan-1,3-dione-fused benzene ring. The structures and properties of all target molecules were investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed, and structure–property relationships were evaluated. Electron donors attached at the C-2 position through π systems of various lengths affect the studied properties most significantly. The side donors at C-4 and C-7 can be described as auxiliary and do not dominate the observed properties. However, thiophene is a more efficient donor than N,N-dimethylaniline in this respect. Hence, indan-1,3-dione bearing a piperidylthiophene donor connected through a propenylidene spacer at C-2 completed with two side thiophen-2-ylethynyl branches at C-4 and C-7 showed the highest figure of merit among the studied properties.
Published: 2015
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13. Incorporation of a ferrocene unit in the π-conjugated structure of donor-linker-acceptor (D-π-A) chromophores for nonlinear optics (NLO)

Author: Sylvain Achelle, Jean-Yves Saillard, Sébastien Gauthier, Alberto Barsella, Françoise Robin-le Guen, Raphaël J. Durand, Samia Kahlal, Maxime Ducamp, Nolwenn Cabon, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: Paper, Materials science, Nonlinear optics, General Chemical Engineering, Conjugated bridges, DFT calculation, Conjugated structures, Electrons, Conjugated system, Nonlinear optical properties, 010402 general chemistry, Iron compounds, 01 natural sciences, chemistry.chemical_compound, Synthesis, Moiety, Charge Transfer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Process Chemistry and Technology, Organic polymers, Electronwithdrawing, Organometallics, Optics, Chromophore, Chromophores, Intramolecular charge transfers, Acceptor, 0104 chemical sciences, Electrochemical behaviour, Crystallography, Ferrocene, chemistry, Electron-donating, Intramolecular force, Polar effect, Analogs
Abstract: In this paper we describe the synthesis, the electrochemical behaviour as well as the linear and nonlinear optical (NLO) properties of two push-pull derivatives bearing pyranylidene electron donating fragment, pyrimidine/methyl pyrimidinium electron withdrawing moiety and a ferrocene part in the π-conjugated bridge. The properties of these two compounds were compared to their analogues without ferrocene or pyranylidene fragments. Experimental results were completed with DFT calculations to gain further insight into the intramolecular charge transfer (ICT). All the results indicate a significant charge transfer through the ferrocene unit. The ICT is however more limited than in all organic analogues.
Published: 2018
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14. Triphenylamine-based allylidenemalononitrile chromophores synthesis, and photophysical and second-order nonlinear optical properties

Author: Zeynel Seferoğlu, Françoise Robin-le Guen, Alberto Barsella, Sylvain Achelle, Ergin Keleş, Nurgül Seferoğlu, Emine Çatal, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Scientific and Technological Research Council of Turkey (TUBITAK) [215Z567], Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Chemistry, 02 engineering and technology, General Chemistry, Chromophore, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, Branching (polymer chemistry), Triphenylamine, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Nonlinear optical, Aniline, Materials Chemistry, [CHIM]Chemical Sciences, Thermal stability, 0210 nano-technology
Abstract: International audience; A series of chromophores based on a mono-, di- or tri-substituted triphenylamine core and allylidenemalononitrile fragments has been designed. The linear and second order nonlinear optical properties as well as thermal stability of the chromophores have been studied experimentally. Structure-property relationships, in terms of the branching effect on the triphenylamine core and the influence of the aniline/coumarin part on the photophysical properties and NLO response, have been highlighted. The experimental results have been rationalized by theoretical calculations.
Published: 2018
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15. Mono- and Diplatinum Polyynediyl Complexes as Potential Push–Pull Chromophores: Synthesis, Characterization, TD-DFT Modeling, and Photophysical and NLO Properties

Author: Alberto Barsella, Vincent Dorcet, Thierry Roisnel, Sébastien Gauthier, Françoise Robin-le Guen, Ariel Porter, Denis Jacquemin, Patricia Guevara Level, Sylvain Achelle, Nicolas Le Poul, RENARD, NICOLAS, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Center of Natural Sciences, Northern Kentucky University, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Chimie, Electrochimie Moléculaires et Chimie Analytique (CEMCA), Université de Brest (UBO)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), We deeply thank Prof. Bertrand Caro for his insightful advices and helpful comments. A.P. thanks the Northern Kentucky University (NKU) STEM International Research and Scholarly Exchange Program (IRSEP) for providing her internship and the NKU Center for Global Engagement and International Affairs for financial support. The theoretical calculations were carried out with the resources of the CCIPL in Nantes and of the IDRIS/CINES in Paris., Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Subjects: Polyyne, Platinum complexes, chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, Electrochemistry, NLO, 01 natural sciences, Inorganic Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, pyranylidene compounds, Chemistry, Ligand, Organic Chemistry, Second-harmonic generation, Chromophore, [CHIM.COOR] Chemical Sciences/Coordination chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Characterization (materials science), [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Crystallography, [CHIM.THEO] Chemical Sciences/Theoretical and/or physical chemistry, Density functional theory, 0210 nano-technology, Platinum
Abstract: The syntheses, photophysical and electrochemical characterizations of four new mono- and diplatinum polyynediyl complex chromophores end-capped with diphenylpyranylidene and pentafluorophenyl moieties are described. The nonlinear optical properties (NLO) of these compounds have been investigated using the electric-field-induced second harmonic generation (EFISH) technique. While the inductive electron-withdrawing pentafluorophenyl ligand, the length of the polyyne linkers, and the number of platinum centers do not seem to significantly affect the NLO responses of these complexes, their structural configuration (V-shape vs linear shape) plays a significant role., La synthèse et les caractérisations photophysiques et électrochimiques de quatre chromophores mono - et diplatine polyynediyles porteurs de motifs diphenylpyranylidènes et pentafluorophényles sont décrits. Les propriétés d’optique non linéaire (NLO) de ces composés ont été étudiées par méthode EFISH. Les résultats montrent que la configuration structurale (forme en V vs. linéaire) du complexe affecte la réponse NLO, alors que la présence d’un ligand pentafluorométhyle, la longueur des espaceurs polyynes et le nombre de centres métalliques (Pt) semblent peu influents.
Published: 2018
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16. Structural changes in MII dithione/dithiolato complexes (M = Ni, Pd, Pt) on varying the dithione functionalization

Author: Alain Fort, Maria Laura Mercuri, Salahuddin S. Attar, Luca Pilia, Paola Deplano, Luciano Marchiò, Davide Espa, Alberto Barsella, and Angela Serpe
Subjects: Chemistry, Supramolecular chemistry, Space group, Triad (anatomy), General Chemistry, Crystal structure, Condensed Matter Physics, Acceptor, Crystallography, medicine.anatomical_structure, medicine, General Materials Science, Orthorhombic crystal system, Isostructural, Monoclinic crystal system
Abstract: The Ni triad [M(R2pipdt)(dmit)] based on donor/acceptor S,S′ ligands, where R2pipdt = 1,4-diisopropyl-piperazine-2,3-dithione (acceptor) and dmit = 2-thioxo-1,3-dithiole-4,5-dithiolato (donor), was completed by preparing and characterizing the Pd(2) and Pt(3) compounds in addition to the already known Ni(1) complex. The rationale behind the work was to compare the properties and structures inside the triad with those of the corresponding Ni(4), Pd(5) and Pt(6) complexes where R = Bz. Minor changes in the properties as redox active nonlinear second-order (NLO) chromophores were observed in solution for the two triads. Instead, different structural features, reflected by changes in the diffuse reflectance spectra, were observed in their crystals on changing R from Bz to Pri in the piperazine ring and also, more surprisingly, inside the triads. 2 (isostructural with 1) and 3 crystallized in monoclinic P21/n and orthorhombic Pbca space groups, respectively. The crystal packings of 2 and 3 are also markedly different. In particular 1 and 2 form head-to-tail dimers whereas 3 forms supramolecular layers characterized by a partial stack between the molecular planes. Large differences in the crystal structures, induced by the diverse number and types of interactions exchanged by the peripheral fragments of the ligands, were found in the Bz-triad. Indeed, the molecules are stacked in a head-to-head and in a head-to-tail fashion in 4 and in 5/6, respectively. Moreover, significantly different packings were observed. The Hirshfeld surface analysis was used to provide a detailed description of the main types of interactions involved in the crystal packing of the six complexes.
Published: 2015
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17. BODIPY-Bridged Push-Pull Chromophores for Nonlinear Optical Applications

Author: Gilles Ulrich, Alberto Barsella, Raymond Ziessel, Alex Boeglin, and Song-Lin Niu
Subjects: chemistry.chemical_compound, Chemistry, Solvatochromism, Moiety, Hyperpolarizability, Protonation, Physical and Theoretical Chemistry, BODIPY, Tetracyanoethylene, Chromophore, Photochemistry, Acceptor, Atomic and Molecular Physics, and Optics
Abstract: A set of linear and dissymmetric BODIPY-bridged push-pull dyes are synthesized. The electron-donating substituents are anisole and dialkylanilino groups. The strongly electron-accepting moiety, a 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) group, is obtained by insertion of an electron-rich ethyne into tetracyanoethylene. A nonlinear push-pull system is developed with a donor at the 5-position of the BODIPY core and the acceptor at the 2-position. All dyes are fully characterized and their electrochemical, linear and nonlinear optical properties are discussed. The linear optical properties of dialkylamino compounds show strong solvatochromic behavior and undergo drastic changes upon protonation. The strong push-pull systems are non-fluorescent and the TCBD-BODIPY dyes show diverse photochemistry and electrochemistry, with several reversible reduction waves for the tetracyanobutadiene moiety. The hyperpolarizability μβ of selected compounds is evaluated using the electric-field-induced second-harmonic generation technique. Two of the TCBD-BODIPY dyes show particularly high μβ (1.907 μm) values of 2050 × 10(-48) and 5900 × 10(-48) esu. In addition, one of these dyes shows a high NLO contrast upon protonation-deprotonation of the donor residue.
Published: 2014
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18. NLO Behavior of Polymers Containing Y-Shaped Chromophores

Author: Fabio Borbone, Alessia Quatela, Alberto Barsella, Antonio Carella, Roberto Centore, Antonio Roviello, Ugo Caruso, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Carella, Antonio, Borbone, Fabio, Caruso, Ugo, Centore, Roberto, Roviello, Antonio, A., Barsella, A., Quatela, and Masson, Beatrice
Subjects: chemistry.chemical_classification, Materials science, Polymers and Plastics, Organic Chemistry, Relaxation (NMR), Nonlinear optics, Second-harmonic generation, Polymer, Chromophore, Condensed Matter Physics, chemistry.chemical_compound, chemistry, Polymer chemistry, Materials Chemistry, Thermal stability, Physical and Theoretical Chemistry, Glass transition, Polyurethane
Abstract: New polyurethanes containing Y-shaped chromophores, symmetrical derivatives of 4-(dicyanomethylene)-2-methyl-6- [p- (dimethylamino)styryl]-4H-pyran, have been prepared. The polymers show high glass transition temperatures (Tg) and a good thermal stability. SHG measurements on poled polymer films of the synthesized polymers have been carried out and a maximum d 33 of 15 pm·v -1 has been found at 1368 nm fundamental wavelength. Time stability measurements on the most active polymer have shown that after the initial fast relaxation, the d 33 value remains constant at 80 °C for 60 d.
Published: 2007
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19. Role of the Acceptor in Tuning the Properties of Metal [M(II) = Ni, Pd, Pt] Dithiolato/Dithione (Donor/Acceptor) Second-Order Nonlinear Chromophores: Combined Experimental and Theoretical Studies

Author: Luca Pilia, Angela Serpe, Alberto Barsella, Alain Fort, Christodoulos Makedonas, M. Laura Mercuri, Luciano Marchiò, Paola Deplano, Christiana A. Mitsopoulou, and Davide Espa
Subjects: chemistry.chemical_element, Triclinic crystal system, Chromophore, Ring (chemistry), Photochemistry, Sulfur, Acceptor, Inorganic Chemistry, Metal, Crystallography, chemistry, visual_art, visual_art.visual_art_medium, Physical and Theoretical Chemistry, Isostructural, Absorption (chemistry)
Abstract: The mixed-ligand complexes [M(II)(Et2dazdt)(mnt)] (M = Ni, 1; Pd, 2; Pt, 3) [Et2dazdt = N,N'-diethyl-perhydrodiazepine-2,3-dithione; mnt = maleonitrile-2,3-dithiolate] have been prepared and fully characterized. X-ray diffractometric studies on 1-3 (the structure of 1 was already known) show that the crystals are isostructural (triclinic, P-1), and two independent molecular entities are present in the unit cell. These entities differ in the orientation of the ethyl substituents with respect to the epta-atomic ring. In the C2S2MS2C2 dithiolene core the four sulfur atoms define a square-planar coordination environment of the metal where the M-S bond distances involving the two ligands are similar, while the C-S bond distances in the C2S2 units exhibit a significant difference in Et2dazdt (dithione) and mnt (dithiolato) ligands. 1-3 show in the visible region one or two moderately strong absorption peaks, having ligand-to-ligand charge-transfer (CT) character with some contribution of the metal, and show negative solvatochromism and molecular quadratic optical nonlinearity, which was determined by the EFISH (electric-field-induced second-harmonic generation) technique. These complexes are redox active and show two reversible reduction waves and one irreversible oxidation wave. Theoretical calculations based on DFT and TD-DFT calculations on complexes 1-3 as well as on [Pt(Bz2pipdt)(mnt)] (4) and [Pt(Bz2pipdt)(dmit)] (5) highlight the factors which affect the optical properties of these second-order redox-active NLO chromophores. Actually, the torsion angle of the dithione system (δ2) inversely correlates either with the oscillator strengths of the main transition of the complexes or with their beta values. The high beta value of 5 can be attributed both to its lowest torsion angles and to the extent of the π system of its dithiolate ligand, dmit.
Published: 2014
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20. Incorporation of a platinum center in the pi-conjugated core of push-pull chromophores for nonlinear optics (NLO)

Author: Sébastien Gauthier, Sylvain Achelle, Alberto Barsella, Jean-Yves Saillard, Samia Kahlal, Raphaël J. Durand, Françoise Robin-le Guen, Nicolas Le Poul, Laurianne Wojcik, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Chimie, Electrochimie Moléculaires et Chimie Analytique (CEMCA), Université de Brest (UBO)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), R. D. thanks the French Ministry of Higher Education and Research for Ph. D. funding. The GENCI-CINES and GENCI-IDRISS French national computer centers are acknowledged for computational resources [grant x2016-087367], Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Diazine, 010405 organic chemistry, Stereochemistry, Intramolecular Charge Transfer, Pyranylidene, chemistry.chemical_element, Nonlinear optics, Chromophore, Conjugated system, 010402 general chemistry, 01 natural sciences, Redox, Acceptor, 0104 chemical sciences, Inorganic Chemistry, Crystallography, chemistry.chemical_compound, Platinum Complexes, chemistry, Intramolecular force, Nonlinear Optics, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Platinum, ComputingMilieux_MISCELLANEOUS
Abstract: In this article, we describe the synthesis, redox characteristics, and linear and nonlinear optical (NLO) properties of seven new unsymmetrical push-pull diacetylide platinum-based complexes. These D-π-Pt-π-A complexes incorporate pyranylidene ligands as pro-aromatic donor groups (D), diazine rings as electron-withdrawing groups (A), and various aromatic fragments (styryl or thienylvinyl) as π-linkers separating the platinum diacetylide unit from the donor and the acceptor groups. This is one of the first examples of push-pull chromophores incorporating a platinum center in the π-conjugated core. The NLO properties of these complexes were compared with those of their purely organic analogues. All compounds (organic and organometallic) exhibited positive μβ values, which dramatically increased upon methylation of the pyrimidine fragment. However, this increase was even more significant in the complexes due to the presence of platinum in the π-conjugated core. The effects of the linker on the redox and spectroscopic properties of the complexes are also discussed. In addition, DFT calculations were performed in order to gain further insight into the intramolecular charge transfer (ICT) occurring through the platinum center.
Published: 2017
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21. Styryl-based NLO chromophores: synthesis, spectroscopic properties, and theoretical calculations

Author: Zeynel Seferoğlu, Yasmina Bayrak, Nurgül Seferoğlu, Sylvain Achelle, Alberto Barsella, Ergin Yalçın, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), We are grateful to The Scientific and Technological Research Council of TURKEY for providing financial support (Project Grant No: 114F296) for this study., Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Non-linear optic (NLO) Push–pull Intramolecular charge transfer Styryl dyes DFT calculations, 010405 organic chemistry, Chemistry, Organic Chemistry, Scalar (mathematics), Hyperpolarizability, Chromophore, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, 3. Good health, Dipole, Drug Discovery, Physical chemistry, [CHIM]Chemical Sciences, Density functional theory, Thermal stability, Tensor, Thermal analysis
Abstract: A novel series of styryl-based chromophores is synthesized, the constituents of which are characterized by UV-Vis, NMR, mass spectrometry, and thermal analysis. The chromophores show good solubility in MeOH, THF, and CH2Cl2. They also show good thermal stability for practical applications. Density functional theory calculations are employed in order to ascertain the structural, molecular, and electronic properties of the dyes. Moreover, the second order nonlinear optical (NLO) responses of the dyes are measured by the electric field induced second harmonic (EFISH) generation method. Relatively high scalar products of the vector component of the first hyperpolarizability tensor and the dipole moment vector (mu beta) are obtained for some of the compounds. (C) 2015 Elsevier Ltd. All rights reserved.
Published: 2017
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22. Dipolar NLO Chromophores Bearing Diazine Rings as π-Conjugated Linkers

Author: Oldřich Pytela, Alberto Barsella, Milan Klikar, Kokou D. Dorkenoo, Sylvain Achelle, Françoise Robin-le Guen, Aleš Růžička, Filip Bureš, Pascal Le Poul, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institute of Organic Chemistry and Technology [University of Pardubice], University of Pardubice, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), M. K. and F. B. are indebted to the Ministry of Education, Youthand Sports of the Czech Republic (specific research)., Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Diazine, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Conjugated system, Electron acceptor, Chromophore, 010402 general chemistry, Photochemistry, Triphenylamine, 01 natural sciences, 0104 chemical sciences, Pyridazine, chemistry.chemical_compound, chemistry, Polarizability, Intramolecular force
Abstract: International audience; The synthesis of a series of push-pull derivatives bearing triphenylamine electron-donating group, cyclopenta[c]thiophen-4,6-dione electron acceptor and various π-linkers including (hetero)aromatic fragments is reported. All target chromophores with systematically varied π-linker structure were further investigated by electrochemistry, absorption measurements, and EFISH experiments in conjunction with DFT calculations. Based on electrochemical and photophysical measurements, when a polarizable 2,5-thienylene moiety is embedded into the chromophore π-backbone the highest intramolecular charge transfer (ICT) is observed. Benzene, pyrimidine, and pyridazine derivatives exhibit lower polarizability and extent of the ICT across these π-linkers. The elongation of the π-conjugated system via additional ethenylene linker results in a significant reduction of the HOMO-LUMO gap and an enhancement of the NLO response. Whereas it does not significantly influence electrochemical and linear optical properties, the orientation of the pyrimidine ring seems to be a key parameter on the μβ value due to significant variation of the dipolar moment (μ) value. In 2a and 2c, pyrimidine is oriented to behave as an acceptor and thus generate dipolar molecule with μ above 5 D, whereas in 2b and 2d ground state dipole moment is significantly reduced. This study seems to indicate a high aromaticity of pyrimidine and pyridazine derivatives, close to the benzene analogues and significantly higher than thiophene analogues.
Published: 2017
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23. Syntheses of four new pyridinium phenolates with caged phenolate functionalities as chromophores for quadratic optics

Author: Alberto Barsella, Hélène Chaumeil, and Emel Ay
Subjects: chemistry.chemical_classification, Pyridinium Compounds, Organic Chemistry, Nonlinear optics, Chromophore, Photochemistry, Biochemistry, Combinatorial chemistry, Chemical synthesis, chemistry.chemical_compound, chemistry, Zwitterion, Drug Discovery, Pyridinium, Alkyl, Cyclophane
Abstract: Semi-empirical calculations as well as our preliminary studies indicate an increase of the nonlinear response of pyridinium phenolates with the raise of their interplanar angle. Unfortunately, the tendency of previously synthesized zwitterionic compounds to form aggregates prevents their use in electro-optical devices. In order to understand the process of aggregation and to circumvent it, the syntheses of new pyridinium phenolates bearing alkyl chains of various length, caging the phenolate functionality, have been achieved and are described herein.
Published: 2012
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24. Combined Experimental and Theoretical Study on Redox-Active d8 Metal Dithione–Dithiolato Complexes Showing Molecular Second-Order Nonlinear Optical Activity

Author: Maria Laura Mercuri, Christiana A. Mitsopoulou, Alberto Barsella, Paola Deplano, Davide Espa, Luciano Marchiò, Angela Serpe, Christodoulos Makedonas, Alain Fort, and Luca Pilia
Subjects: Chemistry, Ligand, Solvatochromism, chemistry.chemical_element, Triad (anatomy), Sulfur, Inorganic Chemistry, Metal, Nickel, Crystallography, medicine.anatomical_structure, Computational chemistry, visual_art, medicine, visual_art.visual_art_medium, Order (group theory), Physical and Theoretical Chemistry, Cyclic voltammetry
Abstract: Synthesis, characterization, NLO properties, and theoretical studies of the mixed-ligand dithiolene complexes of the nickel triad [M(II)(Bz(2)pipdt)(mnt)] (Bz(2)pipdt = 1,4-dibenzyl-piperazine-3,2-dithione, mnt = maleonitriledithiolato, M(II) = Ni, 1, Pd, 2, Pt, 3) are reported. Molecular structural characterization of 1-3 points out that four sulfur atoms are in a slightly distorted square-planar geometry. While the M-S bond distances are only slightly different, comparison of the C-C and C-S bonds in the C(2)S(2)MS(2)C(2) core allows us to point out a significant difference between the C-C and the C-S distances in Bz(2)pipdt and mnt. These findings suggest assigning a dithiolato character to mnt (pull ligand) and a dithione one (push ligand) to Bz(2)pipdt. Cyclic voltammetry of 1-3 exhibits two reversible reduction waves and a broad irreversible oxidation wave. These complexes are characterized in the visible region by a peak of moderately strong intensity, which undergoes negative solvatochromism. The molecular quadratic optical nonlinearities were determined by the EFISH technique, which provided the following values μβ(λ) (10(-48) esu) = -1436 (1), -1450 (2), and -1950 (3) converted in μβ(0) (10(-48) esu) = -463 (1), -684 (2), and -822 (3), showing that these complexes exhibit large negative second-order polarizabilities whose values depend on the metal, being highest for the Pt compound. DFT and TD-DFT calculations on 1-3 allow us to correlate geometries and electronic structures. Moreover, the first molecular hyperpolarizabilities have been calculated, and the results obtained support that the most appealing candidate as a second-order NLO chromophore is the platinum compound. This is due to (i) the most extensive mixture of the dithione/metal/dithiolato orbitals, (ii) the influence of the electric field of the solvent on the frontier orbitals that maximizes the difference in dipole moments between the excited and the ground state, and (iii) the largest oscillator strength in the platinum case vs nickel and palladium ones.
Published: 2011
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25. Variation of the Backbone Conjugation in NLO Model Compounds: Torsion-Angle-Restricted, Biphenyl-Based Push-Pull-Systems

Author: Marcel Mayor, Alberto Barsella, Alain Fort, Alex Boeglin, David Vonlanthen, and Jürgen Rotzler
Subjects: chemistry.chemical_classification, Biphenyl, Tertiary amine, Chemistry, Stereochemistry, Oscillator strength, Organic Chemistry, Nitro compound, Nonlinear optics, Dihedral angle, Chromophore, chemistry.chemical_compound, Crystallography, Physical and Theoretical Chemistry, Methylene
Abstract: Terminal piperidinyl- and nitro-functionalized biphenyls, bridged between the 2 and 2prime positions by a variable number of methylene groups, are synthesized and fully characterized. These push-pull systems with defined and restricted torsion angles between their phenyl rings are ideal model compounds to investigate the influence of the chromophore's conjugation in nonlinear optic (NLO) responses. A general synthetic route that can be implemented to access these model compounds is reported, starting from dibromo or ditriflate biphenyls. Hartwig-Buchwald cross-coupling, a selective azacycloalkylation of diaminobiphenyls and a mild oxidation of primary amines to nitro groups in the presence of a tertiary amine summarizes the synthetic pathway towards the desired model compounds. NLO properties of the series of torsionally constrained push-pull biphenyls are collected by electric-field-induced second-harmonic generation (EFISH) experiments. The results agree qualitatively with semi-empirical simulations based on the AM1 Hamiltonian. A linear dependence of the quadratic response on the cos2(Phi) of the inter-aryl dihedral angle is observed, which points to oscillator strength loss as the dominant effect of increasing backbone twist.
Published: 2010
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26. Proaromatic pyranylidene chalcogen analogues and cyclopenta[c]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores

Author: Sylvain Achelle, Françoise Robin-le Guen, Alberta Barsella, Parmeshwar Bapurao Solanke, Nolwenn Cabon, Bertrand Caro, Filip Bureš, Jan Podlesný, Milan Klikar, Oldřich Pytela, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), 638857, ERC, European Research Council, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chalcogenopyranylidene, General Chemical Engineering, Fundamental properties, 010402 general chemistry, Photochemistry, 01 natural sciences, push-pull, chemistry.chemical_compound, Chalcogen, Charge transfer, Thiophene, Moiety, Molecule, Chalcogenopyranylidene, [CHIM]Chemical Sciences, Push pull, chemistry.chemical_classification, 010405 organic chemistry, Process Chemistry and Technology, Electronwithdrawing, charge transfer, Chromophore, Electron acceptor, Push-pull chromophores, Chromophores, Acceptor, Structural variations, 0104 chemical sciences, polymethines, non linear optics, Polymethines, chemistry, Pyran, Electron acceptor moieties
Abstract: International audience; Fifteen new push-pull chromophores based on a proaromatic pyranylidene donor and its chalcogen analogues and various electron acceptor moieties were synthesized in a straightforward manner. These model molecules were designed and prepared to investigate the concept of proaromaticity as a tool to tune the fundamental properties of push-pull systems. All target chromophores with systematically varied structure were further investigated by electrochemistry, absorption spectra, and EFISH experiment in conjunction with DFT calculations. Employing structural variations such as chalcogen/acceptor replacement, extension of the π-system, and the position of substitution along the pyran ring, the HOMO-LUMO gap can be tuned within the range of 2.18 to 1.41 eV. A new and powerful electron withdrawing moiety, combining features of polarizable thiophene and successful indane-1,3-dione acceptor, cyclopenta[c]thiophen-4,6-dione (ThDione) has also been developed. © 2016 Elsevier Ltd
Published: 2016
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27. ChemInform Abstract: Styryl-Based NLO Chromophores: Synthesis, Spectroscopic Properties, and Theoretical Calculations

Author: Sylvain Achelle, Zeynel Seferoğlu, Nurgül Seferoğlu, Ergin Yalçın, Yasmina Bayrak, and Alberto Barsella
Subjects: Dipole, Chemistry, Scalar (mathematics), Physical chemistry, Hyperpolarizability, Thermal stability, Density functional theory, General Medicine, Tensor, Chromophore, Thermal analysis
Abstract: A novel series of styryl-based chromophores is synthesized, the constituents of which are characterized by UV–Vis, NMR, mass spectrometry, and thermal analysis. The chromophores show good solubility in MeOH, THF, and CH2Cl2. They also show good thermal stability for practical applications. Density functional theory calculations are employed in order to ascertain the structural, molecular, and electronic properties of the dyes. Moreover, the second order nonlinear optical (NLO) responses of the dyes are measured by the electric field induced second harmonic (EFISH) generation method. Relatively high scalar products of the vector component of the first hyperpolarizability tensor and the dipole moment vector (μβ) are obtained for some of the compounds.
Published: 2015
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28. Optical components based on two-photon absorption process in functionalized polymers

Author: Alberto Barsella, Kokou D. Dorkenoo, Stéphane Klein, Alain Fort, Gregory Taupier, and V. Stortz
Subjects: chemistry.chemical_classification, Materials science, Optical fiber, Fabrication, business.industry, General Physics and Astronomy, Surfaces and Interfaces, General Chemistry, Polymer, Condensed Matter Physics, Two-photon absorption, Surfaces, Coatings and Films, law.invention, Optics, chemistry, law, Astronomical interferometer, Optoelectronics, Absorption (electromagnetic radiation), business, Refractive index, Electronic circuit
Abstract: We report on the fabrication of basic elements needed in optical circuits in a photopolymerizable resin, using a two-photon absorption (TPA) process to perform a selective polymerization. By taking advantage of the high spatial selectivity of the TPA approach, we can control the value of the local index of refraction in the material and realize permanent optical pathways in the bulk of photopolymerizable matrices. The computer-controlled design of such pathways allows creating optical circuits. As an example of application, optical fibers separated by millimetric distances and placed in arbitrary positions have been connected with moderate losses. Moreover, active components, such as electro-optical Mach–Zehnder interferometers, can be fabricated using photopolymers functionalized with non-linear optical chromophores, in order to be integrated in micro-optical circuits.
Published: 2006
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29. Thiazole azo dyes with lateral donor branch: Synthesis, structure and second order NLO properties

Author: Fabio Borbone, Alberto Barsella, Zahra M. Al-amshany, Angela Tuzi, Reda M. El-Shishtawy, Abdullah M. Asiri, Antonio Roviello, R. M., El Shishtawy, Borbone, Fabio, Z. M., Al amshany, Tuzi, Angela, A., Barsella, A. M., Asiri, and Roviello, Antonio
Subjects: Process Chemistry and Technology, General Chemical Engineering, Hyperpolarizability, EXPERIMENTAL HYPERPOLARIZABILITIES, 1ST HYPERPOLARIZABILITY, Chromophore, BOND-LENGTH ALTERNATION, Photochemistry, MODEL, chemistry.chemical_compound, NONLINEAR-OPTICAL PROPERTIES, PUSH-PULL POLYENES, chemistry, Thermal stability, Diazo, Knoevenagel condensation, ACCEPTOR POLYENES, CRYSTAL-STRUCTURE, ORGANIC-MOLECULES, CHROMOPHORES, Thiazole, Derivative (chemistry), Malononitrile
Abstract: Three azo dyes with a thiazole based donor-π-acceptor structure containing a methoxyphenyl group as the lateral donor branch were synthesized and fully characterized. The formyl azo dye precursor was synthesized using 5-formylaminothiazole derivative as the diazo component and N,N-diethylaninline as the coupling component. Knoevenagel condensation of this precursor with different acceptors, namely, indandione, malononitrile and dicyanovinylindanone afforded the desired nonlinear optical chromophores a–c, respectively. The optical property, thermal stability and second order nonlinear optical activity were evaluated and a single crystal structural characterization was performed for two of the dyes. All nonlinear optical dyes a–c have good nonlinearity and good thermal stability. Compared with dyes a and b, dye c shows more than triple second order nonlinear optical response, the result that makes this molecule an unusual example of asymmetrical 2D charge transfer chromophore.
Published: 2013

30. Improvement of the quadratic non-linear optical properties of pyrimidine chromophores by N-methylation and tungsten pentacarbonyl complexation

Author: Xiaoyang Che, Filip Bureš, Jean-Yves Saillard, Julien Vallet, Alberto Barsella, Sylvain Achelle, Bertrand Caro, Samia Kahlal, Françoise Robin-le Guen, Institut des Sciences Chimiques de Rennes (ISCR), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Institute of Organic Chemistry and Technology, University of Pardubice, Faculty of Chemical Technology, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institute of Organic Chemistry and Technology [University of Pardubice], University of Pardubice, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Pyrimidine, Chemistry, Process Chemistry and Technology, General Chemical Engineering, chemistry.chemical_element, Second-harmonic generation, Nonlinear optics, N methylation, Chromophore, Tungsten, Ring (chemistry), Photochemistry, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Nonlinear system, chemistry.chemical_compound, Computational chemistry
Abstract: International audience; In this contribution, we report the synthesis of two series of compds.: 4-(arylvinyl)-1-methylpyrimidinium derivs. and tungsten pentacarbonyl complexes of 4-(arylvinyl)pyrimidines. Their second order non-linear properties, measured by Elec.-Field Induced Second Harmonic generation (EFISH) method, and their photophys. behavior were thoroughly investigated and compared to the corresponding 4-(arylvinyl)pyrimidines. A strong enhancement of the NLO response was obsd. upon methylation or complexation by W(CO)5 of the pyrimidine ring. DFT theor. calcns. were performed to provide complementary insights on the structure-properties relationships in particular concerning the amplitude of the NLO response.
Published: 2015
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31. Donor-linker-acceptor (D-π-A) diazine chromophores with extended π-conjugated cores: synthesis, photophysical and second order nonlinear optical properties

Author: Sylvain Achelle, Françoise Robin-le Guen, Bertrand Caro, Alberto Barsella, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Diazine, 010405 organic chemistry, General Chemical Engineering, Solvatochromism, Sonogashira coupling, General Chemistry, Chromophore, Conjugated system, 010402 general chemistry, Photochemistry, 01 natural sciences, Acceptor, 0104 chemical sciences, chemistry.chemical_compound, Quinoxaline, chemistry, Intramolecular force, [CHIM]Chemical Sciences
Abstract: The synthesis of a series of push–pull pyrimidine and quinoxaline chromophores with extended π-conjugated cores is reported. Starting from a bromoarylvinyldiazine derivative, the key step in the preparation of the chromophores consists of a Sonogashira cross-coupling reaction. The photophysical properties of the compounds are described. A strong positive emission solvatochromism, typical for dyes presenting Intramolecular Charge Transfer (ICT), is observed, in particular for amino substituted derivatives with larger solvatochromic range than known analogous chromophores with smaller π-conjugated cores. The second order non linear optical (NLO) properties were investigated for some of the compounds and a comparison with the NLO responses of already described diazine chromophores exhibits a significant enhancement of the NLO properties by extension of the π-conjugated core.
Published: 2015
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32. Concise Multigram-Scale Synthesis of Push-Pull Tricyanofuran-Based Hemicyanines with Giant Second-Order Nonlinearity: An Alternative for Electro-optic Materials

Author: Chantal Andraud, Olivier Maury, Alberto Barsella, Yann Bretonnière, J.P. Vola, Evelyne Chastaing, Françoise Soyer, Pierre Le Barny, Jean-Christophe Mulatier, Laurent Divay, Wissam Bentoumi, Pierre-Antoine Bouit, Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Thales Research and Technologies [Orsay] (TRT), THALES, École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and THALES [France]
Subjects: Tricyanofuran, Scale (ratio), business.industry, Chemistry, Organic Chemistry, Nonlinear optics, General Chemistry, Catalysis, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Nonlinear system, Figure of merit, Optoelectronics, business, Push pull, ComputingMilieux_MISCELLANEOUS
Abstract: Highly stable and highly soluble push-pull heptamethine hemicyanines based on the tricyanofuran electron-accepting group can be prepared on a 15 g scale. The compounds display giant second-order nonlinear figure of merit, μβ of up to 31,000×10(-48) esu, and lead to a poled material with a second-order nonlinear response, r33 of 90 pm V(-1) at 1.06 μm.
Published: 2014
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33. Large Second-Order NLO Activity in Poly(4-vinylpyridine) Grafted with PdII and CuII Chromophoric Complexes with Tridentate Bent Ligands Containing Heterocycles

Author: Fabio Borbone, Principia Dardano, Pasqualino Maddalena, Ugo Caruso, Stefano Lettieri, Antonio Carella, Giuseppina Roviello, Alberto Barsella, Angela Tuzi, Borbone, Fabio, Carella, Antonio, Caruso, Ugo, Roviello, Giuseppina, Tuzi, Angela, Dardano, Principia, Lettieri, S., Maddalena, Pasqualino, and Barsella, A.
Subjects: chemistry.chemical_classification, Stereochemistry, Ligand, Bent molecular geometry, chemistry.chemical_element, Polymer, Copper, Inorganic Chemistry, Metal, chemistry.chemical_compound, chemistry, visual_art, Polymer chemistry, Pyridine, Acentric factor, visual_art.visual_art_medium, Palladium
Abstract: Two N-salicylidene-N'-acylhydrazines tridentate ligands containing heterocycles were prepared and utilized for the synthesis of mononuclear acentric complexes of Cu-II and Pd-II and pyridine serves as an additional ligand ((MLPy)-Py-x, M = metal, L-x = ligand). Characterization also includes single-crystal X-ray diffraction analysis. These complexes show high second-order nonlinear optical activity (mu beta = 620 x 10(-48)esu for both (CuLPy)-Py-II and (PdLPy)-Py-II and mu beta = 1600 x 10(-48) and 1400 x 10(-48) esu for (CuLPy)-Py-I and (PdLPy)-Py-I, respectively, at incident wavelength of 1907 nm). The properties of polymers (PMLx) obtained by grafting poly(4-vinyl-pyridine) with fragments of the complexes are also reported. The polymers exhibit good thermal stability, high glass-transition temperatures and the absence of crystallinity. The second-order nonlinear optical (NLO) properties of thin, transparent poled films, prepared by spin coating and thermal corona poling, were investigated for some of the polymers. The value of the d(33) parameter was measured at 1064 and 1500 nm (i.e., with and without resonance contribute). In the latter case, the d33 values are 21 and 12 pm/V for PCuLII and PPdLII, respectively. A high time stability of the NLO properties of these materials was found.
Published: 2008

34. Crosslinkable organic glasses with quadratic nonlinear optical activity

Author: Alberto Barsella, Roberto Centore, Antonio Carella, Loic Mager, Alain Fort, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Masson, Beatrice, Carella, Antonio, Centore, Roberto, L., Mager, A., Barsella, and A., Fort
Subjects: Organic electronics, Benzimidazole, 010405 organic chemistry, Second-harmonic generation, Nonlinear optics, General Chemistry, Chromophore, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Biomaterials, chemistry.chemical_compound, chemistry, Polymerization, Thermal, Materials Chemistry, Organic chemistry, Physical chemistry, Electrical and Electronic Engineering, Thin film
Abstract: In this paper, the use of a pure benzimidazole based dimethacrylic push–pull chromophore has been investigated for the preparation of thin films exhibiting quadratic nonlinear optical (NLO) properties. To stabilize these NLO properties, the chromophore orientation has been frozen in a noncentrosymmetric arrangement by cross-linking the material using thermal polymerization induced by suitable initiators. The films present a very stable quadratic optical activity up to T = 152 °C with SHG coefficient d 33 of 14 pm/V measured at 1.9 μm.
Published: 2007

35. ChemInform Abstract: Methylenepyran Based Dipolar and Quadrupolar Dyes: Synthesis, Electrochemical and Photochemical Properties

Author: Françoise Robin-le Guen, Nikolay Vologdin, Alberto Barsella, B. Caro, Sylvain Achelle, and Sébastien Gauthier
Subjects: chemistry.chemical_compound, Dipole, Nonlinear optical, chemistry, Bistability, Dimer, General Medicine, Cyclic voltammetry, Photochemistry, Electrochemistry, Fluorescence, Redox
Abstract: This paper presents the synthesis of a series of push–pull and quadrupolar π-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I 2 to give, after reduction by Na 2 S 2 O 3 , bismethylenepyran compounds via successive steps. The electrochemical redox properties of methylenepyrans 5 – 9 and extended bismethylenepyrans 10 , 14 , and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bi-stability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of μβ were obtained. A positive dimer effect was also observed for bispyran derivatives.
Published: 2014
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36. Photophysical, amplified spontaneous emission and charge transport properties of oligofluorene derivatives in thin films

Author: Cyrille Monnereau, Loic Mager, Daisuke Hashizume, Delphine Pitrat, Aiko Nakao, Fabrice Mathevet, Alberto Barsella, E. Y. Choi, Leszek Mateusz Mazur, André Jean Attias, Ji Eon Kwon, Dong-Wook Kim, Yiming Xiao, Katarzyna Matczyszyn, Kokou D. Dorkenoo, Jean-Charles Ribierre, Minji Gwon, Benoît Heinrich, Soo Young Park, T. Aoyama, J. W. Wu, Masanobu Uchiyama, Jean-Christophe Mulatier, Chantal Andraud, A. Fort, Marek Samoc, Chimie des polymères (LCP), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institute of Physical and Theoretical Chemistry, Wroclaw University of Science and Technology, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie - UMR5182 (LC), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), RIKEN - Institute of Physical and Chemical Research [Japon] (RIKEN), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut Parisien de Chimie Moléculaire (IPCM), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: Amplified spontaneous emission, Photoluminescence, Materials science, oligofluorene, business.industry, General Physics and Astronomy, Quantum yield, Fluorene, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, Photochemistry, chemistry.chemical_compound, chemistry, Optoelectronics, Charge carrier, Physical and Theoretical Chemistry, Thin film, business, Glass transition, HOMO/LUMO
Abstract: International audience; We investigate the photophysical and amplified spontaneous emission properties of a series of monodisperse solution-processable oligofluorenes functionalized with hexyl chains at the C9 position of each fluorene unit. Thin films of these oligofluorenes are then used in organic field-effect transistors and their charge transport properties are examined. We have particularly focused our attention on the influence of oligofluorene length on the absorption and steady-state fluorescence spectra, on the HOMO/LUMO energy levels, on the photoluminescence lifetime and quantum yield as well as on the amplified spontaneous emission properties and the charge carrier mobilities. Differential scanning calorimetry and X-ray diffraction measurements demonstrate that, among all oligofluorene derivatives used in this study, only the structure and morphology of the pentafluorene film is significantly modified by a thermal treatment above the glass transition temperature, resulting in a 9 nm blue-shift of the fluorescence spectrum without significant changes in the photoluminescence quantum yield and in the amplified spontaneous emission threshold. In parallel, hole field-effect mobility is significantly increased from 8.6 × 10(-7) to 3.8 × 10(-5) cm(2) V(-1) s(-1) upon thermal treatment, due to an increase of crystallinity. This study provides useful insights into the morphological control of oligofluorene thin films and how it affects their photophysical and charge transport properties. Moreover, we provide evidence that, because of the low threshold, the tunability of the amplified spontaneous emission and the photostability of the films, these oligofluorenes are promising candidates for organic solid-state laser applications.
Published: 2014
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37. N, N '-Dibutylbarbituric acid as an acceptor moiety in push-pull chromophores

Author: Tomáš Mikysek, Oldřich Pytela, Milan Klikar, Kokou D. Dorkenoo, Filip Bureš, Zdeňka Padělková, Alberto Barsella, and Sylvain Achelle
Subjects: Absorption spectroscopy, 010405 organic chemistry, Chemistry, Aucun, General Chemistry, Chromophore, 010402 general chemistry, Photochemistry, Electrochemistry, 01 natural sciences, Acceptor, Catalysis, 0104 chemical sciences, Nonlinear optical, Intramolecular force, Materials Chemistry, Moiety, Push pull
Abstract: Twelve novel D-pi-A chromophores with the N, N'-dibutylbarbituric acid acceptor, the N, N-dimethylamino donor and a systematically extended pi-linker were synthesized. The extent of intramolecular charge-transfer, structure-property relationships and nonlinear optical properties were further investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectra, calculations and EFISH experiments.
Published: 2013

38. Synthesis, photophysics and nonlinear optical properties of stilbenoid pyrimidine-based dyes bearing methylenepyran donor groups

Author: Huriye Akdas-Kilig, Françoise Robin-le Guen, Stéphane Aloïse, Jean-Luc Fillaut, Jean-Pierre Malval, Alberto Barsella, Bertrand Caro, Sylvain Achelle, Loic Mager, Arnaud Spangenberg, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut de Science des Matériaux de Mulhouse (IS2M), Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 (LASIRE), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Centrale Lille Institut (CLIL), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique
Subjects: Exciton, Molecular Conformation, Electron, 010402 general chemistry, Photochemistry, Branching (polymer chemistry), 01 natural sciences, chromophores, Physical and Theoretical Chemistry, Fluorescent Dyes, Pyrans, photophysics, heterocycles, 010405 organic chemistry, Chemistry, nonlinear optics, Nonlinear optics, Chromophore, Atomic and Molecular Physics, and Optics, Planarity testing, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Kinetics, Dipole, Nonlinear system, Pyrimidines, Quantum Theory, Spectrophotometry, Ultraviolet, conjugation
Abstract: International audience; The nonlinear properties and the photophysical behavior of two π-conjugated chromophores that incorporate an electron-deficient pyrimidine core (A) and γ-methylenepyrans as terminal donor (D) groups have been thoroughly investigated. Both dipolar and quadrupolar branching strategies are explored and rationalized on the basis of the Frenkel exciton model. Even though a cooperative effect is clearly observed if the dimensionality is increased, the nonlinear optical (NLO) response of this series is moderate if one considers the nature of the D/A couple and the size of the chromophores (as measured by the number of π electrons). This effect was attributed to a disruption in the electronic conjugation within the dyes' scaffold for which the geometry deviates from planarity owing to a noticeable twisting of the pyranylidene end-groups. This latter structural parameter also has a strong influence on the excited-state dynamics, which leads to a very efficient fluorescence quenching.
Published: 2013
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39. Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

Author: B. Caro, Françoise Robin-le Guen, Sylvain Achelle, Alberto Barsella, Nikolay Vologdin, Sébastien Gauthier, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS)
Subjects: Bistability, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Dimer, Organic Chemistry, Nonlinear optics, 010402 general chemistry, Photochemistry, Electrochemistry, 01 natural sciences, Biochemistry, Fluorescence, Redox, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Dipole, chemistry, Drug Discovery, Cyclic voltammetry
Abstract: This paper presents the synthesis of a series of push–pull and quadrupolar π-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I 2 to give, after reduction by Na 2 S 2 O 3 , bismethylenepyran compounds via successive steps. The electrochemical redox properties of methylenepyrans 5 – 9 and extended bismethylenepyrans 10 , 14 , and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bi-stability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of μβ were obtained. A positive dimer effect was also observed for bispyran derivatives.
Published: 2013
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40. Stress birefringence patterning in photopolymer induced by structured illumination

Author: Loic Mager, Christiane Carre, Kokou D. Dorkenoo, Jean-Philippe Bombenger, Alberto Barsella, Gregory Taupier, Groupe d'Optique Non Linéaire et d'Optoélectronique, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Département de Photochimie Générale (DPG), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), Fonctions Optiques pour les Technologies de l'informatiON (FOTON), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Université européenne de Bretagne - European University of Brittany (UEB)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-École Nationale Supérieure des Sciences Appliquées et de Technologie (ENSSAT)-Centre National de la Recherche Scientifique (CNRS)-Télécom Bretagne, Université de Rennes (UR)-Université européenne de Bretagne - European University of Brittany (UEB)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Nationale Supérieure des Sciences Appliquées et de Technologie (ENSSAT)-Télécom Bretagne-Centre National de la Recherche Scientifique (CNRS)
Subjects: Diffraction, Materials science, Polarimetry, (050.1940) Diffraction and gratings: Diffraction, (160.4890) Materials: Organic Material, (260.1440) Physical optics: Birefringence, (260.5430) Physical optics: Polarization, 02 engineering and technology, 01 natural sciences, 010309 optics, Inorganic Chemistry, Stress (mechanics), chemistry.chemical_compound, Optics, Polarization, 0103 physical sciences, Electrical and Electronic Engineering, Physical and Theoretical Chemistry, Spectroscopy, Shrinkage, Acrylate, Birefringence, business.industry, Organic Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Polarization (waves), Atomic and Molecular Physics, and Optics, Electronic, Optical and Magnetic Materials, Organic Material, Photopolymer, chemistry, Optoelectronics, 0210 nano-technology, business
Abstract: 4 pages; International audience; We report on the stress birefringence distribution induced by the photopatterning of a multifunctional crosslinkable acrylate monomer sensitized in the visible range. The patterning of this material, prepared in a glass cell of a few tens of microns thickness, is obtained through illumination in a two steps process. The first step is performed using an illumination pattern with a high contrast and a low spatial frequency. The second one is a uniform illumination. The discrepancies in the shrinkage experimented by the material leads to the apparition of patterned stress birefringence revealed through polarimetry and diffraction measurements.
Published: 2013
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41. Synthesis and photophysical investigation of a series of push-pull arylvinyldiazine chromophores

Author: Alberto Barsella, Sylvain Achelle, Françoise Robin-le Guen, Christine Baudequin, Bertrand Caro, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: chemistry.chemical_classification, Photons, Luminescence, Vinyl Compounds, 010405 organic chemistry, Chemistry, Organic Chemistry, Solvatochromism, Chromophore, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Aldehyde, 0104 chemical sciences, Absorption, Pyrimidines, Molecule, Aldol condensation, Colorimetry, Spectrophotometry, Ultraviolet, Absorption (chemistry), Excitation
Abstract: International audience; A new series of push-pull arylvinyldiazines has been efficiently prepared by aldol condensation between the appropriate methyldiazine and aromatic aldehyde. The optical absorption and emission properties of these chromophores were studied in different solvents and media. These compounds act as polarity sensors with a strong positive emission solvatochromism. This behavior suggests a highly polar emitting state, which is characteristic of compounds that undergo an internal charge transfer upon excitation. These molecules also exhibit halochromic properties and are potential colorimetric and luminescence pH sensors. The second-order nonlinear properties have been investigated for some of the compounds, and large and positive μβ are obtained, in particular, for pyrimidine derivatives.
Published: 2012
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42. New Cross-Linkable Polymers with Huisgen Reaction Incorporating High μβ Chromophores for Second-Order Nonlinear Optical Applications

Author: Loic Mager, Yann Pellegrin, Yann Bretonnière, Virginie Silvestre, Wissam Bentoumi, Kokou D. Dorkenoo, Errol Blart, Clément Cabanetos, Chantal Andraud, Laurent Fontaine, Alberto Barsella, Fabrice Odobel, Véronique Montembault, Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie - UMR5182 (LC), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Subjects: Materials science, General Chemical Engineering, Radical polymerization, 02 engineering and technology, Activation energy, Huisgen cycloaddition reaction, 010402 general chemistry, Photochemistry, 01 natural sciences, chemistry.chemical_compound, Polymer chemistry, Materials Chemistry, electro-optic, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Poling, General Chemistry, Polymer, Chromophore, 021001 nanoscience & nanotechnology, Polyene, methacrylate polymer, radical polymerization, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, push-pull chromophore, second-order nonlinear optic, Polar effect, Surface modification, 0210 nano-technology, cross-linking
Abstract: We report herein the synthesis, the functionalization, and the successful radical polymerization of very nonlinear optical (NLO) active push–pull polyene chromophores (CPO). Second, the thermal Huisgen cyclo-addition cross-linking reaction was implemented, and it proved to be fully compatible with a polyene-based push–pull chromophore. Toward this goal, PMMA-co-CPO-3 and two cross-linkable polymers (PCC1-CPO-3 and PCC2-CPO-3) were first prepared and characterized by a modified Teng and Man technique performed in transmission. These first series of polymers were not compatible with the applied poling conditions because an irreversible film degradation was systematically observed at a temperature significantly lower than the cross-linking temperature. Consequently, a second series of polymers was prepared, in which the cross-linking temperature was decreased by functionalizing acetylenic moieties with ester electron withdrawing groups, which decrease the activation energy of the thermal Huisgen cyclo-additi...
Published: 2012
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43. Redox-switchable chromophores based on metal (Ni, Pd, Pt) mixed-ligand dithiolene complexes showing molecular second-order nonlinear-optical activity

Author: Alain Fort, Alberto Barsella, Neil Robertson, Luca Pilia, Davide Espa, Paola Deplano, Angela Serpe, Maria Laura Mercuri, Simon Dalgleish, and Luciano Marchiò
Subjects: Models, Molecular, Solvatochromism, chemistry.chemical_element, Hyperpolarizability, Chromophore, Photochemistry, Crystallography, X-Ray, Ligands, Inorganic Chemistry, Metal, Nickel, chemistry, visual_art, visual_art.visual_art_medium, Organometallic Compounds, Sulfhydryl Compounds, Physical and Theoretical Chemistry, Platinum, Oxidation-Reduction, Palladium, Group 2 organometallic chemistry
Abstract: The synthesis and full characterization of the redox-active nickel triad mixed-ligand dithiolene complexes based on Bz(2)pipdt = 1,4-dibenzylpiperazine-3,2-dithione and dmit = 2-thioxo-1,3-dithiole-4,5-dithiolate ligands are reported. These complexes show a reversibly bleacheable solvatochromic peak and a remarkably high negative molecular first hyperpolarizability, whose values depend on the metal being highest for the platinum(II) compound.
Published: 2011

44. Electronic responses of donor acceptor substituted twisted biphenyls

Author: J. Rotzler, E. Ay, Alberto Barsella, H. Chaumeil, Alain Fort, Marcel Mayor, and Alex Boeglin
Subjects: symbols.namesake, Dipole, Computational chemistry, Oscillator strength, Chemistry, COSMO solvation model, Ab initio, symbols, Density functional theory, Electronic structure, Dihedral angle, Hamiltonian (quantum mechanics), Molecular physics
Abstract: Donor-acceptor biphenyl derivatives are particularly interesting model compounds presenting a charge transfer absorption band because the extent of conjugation, and therefore the amount of charge transfer between the substituents, may be varied by a controllable structural feature, namely the torsion angle between the two phenyl rings. This feature has become even more interesting since chromophores of strong zwitterionic character, synthesized with a twist of nearly 90°, have been shown to exhibit unprecedented quadratic responses [1], over an order of magnitude above that of the best conventional push-pull chromophores. In this context, we have investigated both experimentally and theoretically, two biphenyl based systems with varying inter-aryl angles: a nitro-piperidinyl series [2] of conventional push-pull character and a pyridinium-phenoxide series [3] of zwitterionic character. The results agree qualitatively with semiempirical simulations based on the AM1 Hamiltonian [4] used with the COSMO solvation model [5]. For the first series, the decrease in quadratic response with increasing dihedral angle indicates that oscillator strength loss is the dominant factor. In the second series, the corresponding increase in quadratic response points to the change in dipole moment upon excitation as the leading effect. Here, we will analyze to what extent the more ab initio electronic structure calculations based on the density functional theory may provide more quantitative results in spite of the problems they face in the description of charge transfer systems.
Published: 2010
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45. Structural and Thermal Constraints to the Tectonic Evolution of Foredeep Successions in the Northern Apennines, Italy

Author: Luca Pandolfi, Francesca Meneghini, Sveva Corrado, Luca Aldega, F. Botti, Silvia Palandri, Michele Marroni, and M. Barsella
Subjects: Calcite, chemistry.chemical_compound, Tectonics, chemistry, Shear (geology), Magmatism, Gemology, Shear zone, Petrology, Clay minerals, Geology, Diagenesis
Abstract: A multi-method investigation (structural analysis, organic matter thermal maturity and clay mineralogy) was carried out on highly deformed foredeep successions in the Northern Apennine with special regard to shear zones in the Lago Trasimeno area (Rentella Unit) to unravel the main structural mechanisms and the thermal condition of the Miocene accretionary processes of the Northern Apennines belt. The Rentella Unit consists of a foredeep succession deposited in a paleogeographic domain between the Tuscan and the Umbria-Marche Domains. Meso- and microstructural data indicate shear planes compatible with C-planes (N160°, 45°SW). C-planes veins show dilational jogs and a staircase shape coherent to a top-to-the-NE sense of shear. Type II calcite twins in the shear zone associated veins suggest temperatures of 150-200°C. Temperature-dependent clay minerals and vitrinite reflectance indicate lower maximum paleo-temperatures (
Published: 2008

46. Molecular design and synthesis of 4,8-di(hetero)arylquinazolines with potential applications in quadratic nonlinear optics. Diazines part 48

Author: Alberto Barsella, Alexandrine Busch, Alain Turck, Kamila Nowicka, Chantal Andraud, Nelly Plé, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), and Masson, Beatrice
Subjects: Pharmacology, chemistry.chemical_compound, Quadratic equation, chemistry, Computational chemistry, Organic Chemistry, Quinazoline, Nonlinear optics, Conjugated system, Photochemistry, Cinnoline, Analytical Chemistry, Naphthalene
Abstract: In the aim to define a structure NLO properties relationship, theoretical calculations have been used to investigate the role of different parts (substituents and π-system) of disubstituted conjugated systems based on naphthalene, cinnoline and quinazoline moieties. Using metallation and cross-coupling reactions we report here the synthesis of new 4,8-di(hetero)arylquinazolines and their quadratic NLO properties.
Published: 2007

47. Optical properties and progressive sterical hindering in pyridinium phenoxides

Author: H. Chaumeil, Alain Fort, Vincent Rodriguez, Christiane Carre, Alberto Barsella, Alex Boeglin, Patrice Jacques, Fabien Mançois, V. Diemer, A. Defoin, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), and Masson, Beatrice
Subjects: Steric effects, 010405 organic chemistry, Chemistry, General Physics and Astronomy, Solvation model, Protonation, 010402 general chemistry, Photochemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Dipole, Physical chemistry, Pyridinium, Physical and Theoretical Chemistry, Absorption (chemistry), Acetonitrile
Abstract: Pyridinium phenoxides are model compounds associating large dipole moments with high optical nonlinearities. A progression of sterically hindered forms of such zwitterions has been synthesized in order to investigate their structure/property relationships. Their UV–vis absorption in acetonitrile has been analyzed as a function of concentration in order to assess the presence of aggregates and the level of protonation. The quadratic optical properties have been measured by the EFISH and hyper-Rayleigh techniques and are interpreted via semi-empirical calculations. The solvation model used leads to results that agree with our experimental findings indicating an increased response for intermediate twist angles.
Published: 2007

48. Synthesis of chromophores combining second harmonic generation and two photon induced fluorescence properties

Author: Jean-Claude Vial, Yann Bretonnière, Kamilla Nowika, Cyril Barsu, Alberto Barsella, Patrice L. Baldeck, Alain Fort, Rémy Fortrie, Chantal Andraud, Muriel Hissler, Olivier Maury, Laboratoire de Chimie - UMR5182 (LC), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Spectrométrie Physique (LSP), Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Rennes (ICR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Rennes (UR)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Models, Molecular, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Catalysis, Optics, Two-photon excitation microscopy, Materials Chemistry, ComputingMilieux_MISCELLANEOUS, Fluorescent Dyes, [PHYS.PHYS.PHYS-OPTICS]Physics [physics]/Physics [physics]/Optics [physics.optics], Photons, Molecular Structure, Chemistry, business.industry, Metals and Alloys, Second-harmonic generation, General Chemistry, Chromophore, 021001 nanoscience & nanotechnology, Fluorescence, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Ceramics and Composites, Optoelectronics, 0210 nano-technology, business
Abstract: The design of new chromophores presenting simultaneous SHG and TPEF properties is reported.
Published: 2006
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49. Integrated optical devices in organic materials photopolymerized via one and two-photon absorption

Author: Alain Fort, Alberto Barsella, Kokou D. Dorkenoo, Gregory Taupier, V. Stortz, and Stéphane Klein
Subjects: chemistry.chemical_classification, Optical fiber, Materials science, business.industry, Physics::Optics, Polymer, Two-photon absorption, law.invention, Photopolymer, Polymerization, chemistry, law, Optoelectronics, business, Absorption (electromagnetic radiation), Realization (systems), Refractive index
Abstract: Two different approaches for the realization of permanent optical waveguides in photopolymers have been investigated. The first one is based on light-induced self-written waveguides (LISW), while the second one uses the technique of polymerization induced by two-photon absorption.
Published: 2006
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50. Sterically hindered pyridinium phenoxides as chromophores for quadratic optics

Author: Vincent Diemer, Hélène Chaumeil, Patrice Jacques, Alain Fort, A. Defoin, Christiane Carre, Alberto Barsella, Alex Boeglin, Chimie organique et bioorganique (COB), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Ecole Nationale Supérieure de Chimie de Mulhouse-Centre National de la Recherche Scientifique (CNRS), Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Département de Photochimie Générale (DPG), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), and xxx
Subjects: chemistry.chemical_classification, Chemistry, Aryl halide, Solvatochromism, Aromaticity, Protonation, [CHIM.MATE]Chemical Sciences/Material chemistry, Chromophore, chemistry.chemical_compound, Suzuki reaction, Computational chemistry, Molecule, Pyridinium, Physics::Chemical Physics
Abstract: Polymers doped with non-linear optical (NLO) molecules are key materials in the elaboration of organic NLO devices. In this field, there is an ongoing need for chromophores with large dipole moments and optical non linearities. Here, we consider pyridinium phenoxides, a type of zwitterionic biphenyl-like molecule. A combination of mathematical modelling and some preliminary experimental measurements indicate that the NLO properties of these molecules depend on the twist angle existing between the two aromatic rings. In order to corroborate this structure/activity relationship, different sterically hindered pyridinium phenoxides were synthesized using the Suzuki coupling reaction involving a boronic ester and an aryl halide. We analyze the solvatochromism of the substituted zwitterions in details, determine the chemical equilibrium of protonation and perfom nonlinear optical measurements which are interpreted with the help of semi-empirical calculations.
Published: 2006

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