43 results on '"Guillaume Noirbent"'
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2. Towards new NIR dyes for free radical photopolymerization processes
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Haifaa Mokbel, Guillaume Noirbent, Didier Gigmes, Frédéric Dumur, and Jacques Lalevée
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cyanine ,nir light ,photochemistry ,Science ,Organic chemistry ,QD241-441 - Abstract
The use of cheap and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 µm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is proposed. Remarkably, 11 of them were never synthesized before. Markedly, noncharged structures, negatively charged cyanine bearing Na+ as counter cation, and positively charged cyanines bearing (B(Ph)4−) or (I−) as counter anions were examined as promising NIR light photoinitiating systems. Excellent photoinitiating abilities were found for some reported dyes when used in combination with iodonium salt and amine. Markedly, photothermal effects with a huge heater behavior were also observed for different NIR dye structures. Interestingly, the synthesis of interpenetrating polymer networks (IPNs, e.g., for the polymerization of acrylate/epoxy monomer blends) can also be carried out upon NIR light with the proposed systems.
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- 2021
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3. Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region
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Aude-Héloise Bonardi, Frédéric Dumur, Guillaume Noirbent, Jacques Lalevée, and Didier Gigmes
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photoinitiator ,photopolymerization ,photoredox catalysis ,photoredox catalyst ,Science ,Organic chemistry ,QD241-441 - Abstract
Recent progresses achieved in terms of synthetic procedures allow now the access to polymers of well-defined composition, molecular weight and architecture. Thanks to these recent progresses in polymer engineering, the scope of applications of polymers is far wider than that of any other class of material, ranging from adhesives, coatings, packaging materials, inks, paints, optics, 3D printing, microelectronics or textiles. From a synthetic viewpoint, photoredox catalysis, originally developed for organic chemistry, has recently been applied to the polymer synthesis, constituting a major breakthrough in polymer chemistry. Thanks to the development of photoredox catalysts of polymerization, a drastic reduction of the amount of photoinitiators could be achieved, addressing the toxicity and the extractability issues; high performance initiating abilities are still obtained due to the catalytic approach which regenerates the catalyst. As it is a fast-growing field, this review will be mainly focused on an overview of the recent advances concerning the development of organic and organometallic photoredox catalysts for the photoreticulation of multifunctional monomers for a rapid and efficient access to 3D polymer networks.
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- 2018
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4. 3-Carboxylic Acid and Formyl-Derived Coumarins as Photoinitiators in Photo-Oxidation or Photo-Reduction Processes for Photopolymerization upon Visible Light: Photocomposite Synthesis and 3D Printing Applications
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Mahmoud Rahal, Bernadette Graff, Joumana Toufaily, Tayssir Hamieh, Guillaume Noirbent, Didier Gigmes, Frédéric Dumur, and Jacques Lalevée
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coumarin ,free radical polymerization ,LED ,photocomposites ,direct laser write ,Organic chemistry ,QD241-441 - Abstract
In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical photopolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2) was also examined.
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- 2021
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5. New Donor-Acceptor Stenhouse Adducts as Visible and Near Infrared Light Polymerization Photoinitiators
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Guillaume Noirbent, Yangyang Xu, Aude-Héloise Bonardi, Sylvain Duval, Didier Gigmes, Jacques Lalevée, and Frédéric Dumur
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photoinitiators ,photopolymerization ,visible light ,DASA ,Stenhouse adducts ,push-pull ,Organic chemistry ,QD241-441 - Abstract
Polymerization photoinitiators that can be activated under low light intensity and in the visible range are being pursued by both the academic and industrial communities. To efficiently harvest light and initiate a polymerization process, dyes with high molar extinction coefficients in the visible range are ideal candidates. In this field, Donor-acceptor Stenhouse Adducts (DASA) which belong to a class of recently discovered organic photochromic molecules still lack practical applications. In this work, a series of DASA-based dyes are proposed as photoinitiators for the free radical polymerization of (meth)acrylates upon exposure to a near infrared light (laser diode at 785 nm).
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- 2020
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6. Cascading One-Pot Synthesis of Biodegradable Uronic Acid-Based Surfactants from Oligoalginates, Semi-Refined Alginates, and Crude Brown Seaweeds
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Benvegnu, Freddy Pessel, Guillaume Noirbent, Cédric Boyère, Sacha Pérocheau Arnaud, Tiphaine Wong, Laura Durand, and Thierry
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oligomannuronate ,oligoguluronate ,oligoalginate ,semi-refined alginate ,brown seaweed ,one pot cascade process ,uronic acid-based surfactants ,readily biodegradability ,non-ecotoxicity - Abstract
The present article describes a one-pot and cascade mode process using biocompatible/biodegradable reagents, for simply obtaining surfactant compositions comprising mixtures of d-mannuronic acid and l-guluronic acid directly from oligoalginates or semi-refined alginates (mixtures of alginate, cellulose, hemicellulose, laminaran, and fucan). Simple treatments of partial purification of the reaction crudes (elimination of the salts and/or the residual fatty alcohols) or isolation of the surfactant compositions result in sugar-based compounds having performance levels appropriate to applications in detergency. In addition, the challenging extension of this cascading one-pot synthesis technology to crude milled brown seaweeds was successfully carried out to provide promising surface-active compositions made up of alkyl uronate and alkyl glycoside monosaccharides.
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- 2023
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7. Panchromatic Copper Complexes for Visible Light Photopolymerization
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Bernadette Graff, Didier Gigmes, Frédéric Dumur, Guillaume Noirbent, Céline Dietlin, Jacques Lalevee, Alexandre Mau, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), and Dumur, Frederic
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[CHIM.POLY] Chemical Sciences/Polymers ,heteroleptic complexes ,Radical polymerization ,chemistry.chemical_element ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,chemistry.chemical_compound ,Moiety ,[CHIM.COOR]Chemical Sciences/Coordination chemistry ,photoinitiators ,visible light ,copper complex ,free radical polymerization ,Chemistry ,Ligand ,ferrocene ,Cationic polymerization ,[CHIM.COOR] Chemical Sciences/Coordination chemistry ,021001 nanoscience & nanotechnology ,Copper ,0104 chemical sciences ,[CHIM.POLY]Chemical Sciences/Polymers ,Photopolymer ,Polymerization ,Ferrocene ,photopolymerization ,0210 nano-technology - Abstract
International audience; In this work, eleven heteroleptic copper complexes were designed and studied as photoinitiators of polymerization in three-component photoinitiating systems in combination with an iodonium salt and an amine. Notably, ten of them exhibited panchromatic behavior and could be used for long wavelengths. Ferrocene-free copper complexes were capable of efficiently initiating both the radical and cationic polymerizations and exhibited similar performances to that of the benchmark G1 system. Formation of acrylate/epoxy IPNs was also successfully performed even upon irradiation at 455 nm or at 530 nm. Interestingly, all copper complexes containing the 1,1′-bis(diphenylphosphino)ferrocene ligand were not photoluminescent, evidencing that ferrocene could efficiently quench the photoluminescence properties of copper complexes. Besides, these ferrocene-based complexes were capable of efficiently initiating free radical polymerization processes. The ferrocene moiety introduced in the different copper complexes affected neither their panchromatic behaviors nor their abilities to initiate free radical polymerizations.
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- 2021
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8. In situ generation of Ag nanoparticles during photopolymerization by using newly developed dyes‐based <scp>three‐component</scp> photoinitiating systems and the related <scp>3D</scp> printing applications and their shape change behavior
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Jacques Lalevée, Yijun Zhang, Pu Xiao, Hong Chen, Frédéric Dumur, Didier Gigmes, Fabrice Morlet-Savary, Ke Sun, Guillaume Noirbent, and Shaohui Liu
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Materials science ,Nanocomposite ,Polymers and Plastics ,Cationic polymerization ,02 engineering and technology ,Polyethylene glycol ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Silver nanoparticle ,0104 chemical sciences ,chemistry.chemical_compound ,Photopolymer ,Chemical engineering ,chemistry ,Hexafluorophosphate ,Materials Chemistry ,medicine ,Physical and Theoretical Chemistry ,Swelling ,medicine.symptom ,0210 nano-technology ,Photoinitiator - Abstract
Silver nanoparticles (AgNPs) play a crucial role in biology and medical research as their extensive and efficient antibacterial activity and high electrical and thermal conductivity. However, the generation of them with a certain morphology under mild conditions (under air, solvent-free, room temperature, etc.,) is still a huge challenge. Herein, a simple one-step method is proposed to generate AgNPs in situ at room temperature under air by combining the photopolymerization process with the formation process of AgNPs within a few minutes. In detailed, 12 different dyes based on 2,5-diethylene-cyclopentan-1-one were first synthesized and used as high-performance type II photoinitiator. When using in conjunction of bis-(4-tert-butylphenyl) iodonium hexafluorophosphate (Iod) and ethyl 4-dimethylaminobenzoate (EDB), they can effectively boost the free radical photopolymerization (FRP) of polyethylene glycol diacrylate (PEG-DA) and the cationic photopolymerization (CP) of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate (EPOX) upon irradiation with LED@405 nm. Furthermore, all the formulations containing/without AgNPs can be successfully used to perform the direct laser write experiment. However, even if all of the obtained 3D patterns exhibited reversible swelling performance and shape-memory effects caused by swelling and dehydration for the access to 4D printing, the presence of AgNPs will affect these properties.
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- 2021
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9. Nanostructured Conjugated Polymer for Solar Cell Applications
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Emilie Dauzon, Thanh‐Tuan Bui, Frédéric Dumur, Guillaume Noirbent, Cédric Vancaeyzeele, Fabrice Goubard, Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), CY Cergy Paris Université (CY)-CY Cergy Paris Université (CY), Institut de Chimie Radicalaire (ICR), and Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
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chemistry.chemical_classification ,Conductive polymer ,Materials science ,Nanowire ,Nanotechnology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,02 engineering and technology ,Polymer ,Conjugated system ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,Active layer ,law.invention ,[CHIM.POLY]Chemical Sciences/Polymers ,chemistry ,law ,Nanofiber ,Solar cell ,Copolymer ,0210 nano-technology ,ComputingMilieux_MISCELLANEOUS - Abstract
International audience
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- 2021
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10. Novel Copper Complexes as Visible Light Photoinitiators for the Synthesis of Interpenetrating Polymer Networks (IPNs)
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Mahmoud Rahal, Guillaume Noirbent, Bernadette Graff, Joumana Toufaily, Tayssir Hamieh, Didier Gigmes, Frédéric Dumur, Jacques Lalevée, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Lebanese University [Beirut] (LU), Laboratoire de Matériaux, Catalyse, Environnement et Méthodes Analytiques (MCEMA), MCEMA, and Dumur, Frederic
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[CHIM.MATE] Chemical Sciences/Material chemistry ,CATALYST ,CLAISEN-SCHMIDT CONDENSATION ,Polymers and Plastics ,LED ,REDOX PROPERTIES ,[CHIM.MATE]Chemical Sciences/Material chemistry ,General Chemistry ,free radical photopolymerization ,METAL NANOPARTICLES ,TRANSFER RADICAL-ADDITION ,EXCITED-STATE DYNAMICS ,copper complex ,photocomposite ,laser write ,ADHESIVES ,LIGANDS ,CHALCONES ,PHOTOPOLYMERIZATION - Abstract
International audience; This work is devoted to the study of two copper complexes (Cu) bearing pyridine ligands, which were synthesized, evaluated and tested as new visible light photoinitiators for the free radical photopolymerization (FRP) of acrylates functional groups in thick and thin samples upon light-emitting diodes (LED) at 405 and 455 nm irradiation. These latter wavelengths are considered to be safe to produce polymer materials. The photoinitiation abilities of these organometallic compounds were evaluated in combination with an iodonium (Iod) salt and/or amine (e.g., N-phenylglycine—NPG). Interestingly, high final conversions and high polymerization rates were obtained for both compounds using two and three-component photoinitiating systems (Cu1 (or Cu2)/Iodonium salt (Iod) (0.1%/1% w/w) and Cu1 (or Cu2)/Iod/amine (0.1%/1%/1% w/w/w)). The new proposed copper complexes were also used for direct laser write experiments involving a laser diode at 405 nm, and for the photocomposite synthesis with glass fibers using a UV-conveyor at 395 nm. To explain the obtained polymerization results, different methods and characterization techniques were used: steady-state photolysis, real-time Fourier transform infrared spectroscopy (RT-FTIR), emission spectroscopy and cyclic voltammetry.
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- 2022
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11. Free‐radical polymerization upon near‐infrared light irradiation, merging photochemical and photothermal initiating methods
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Aude Héloïse Bonardi, Guillaume Noirbent, Didier Gigmes, Jacques Lalevée, Fabien Bonardi, Céline Dietlin, Frédéric Dumur, Dumur, Frederic, Institut de Science des Matériaux de Mulhouse (IS2M), 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), Informatique, BioInformatique, Systèmes Complexes (IBISC), Université d'Évry-Val-d'Essonne (UEVE)-Université Paris-Saclay, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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)
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[CHIM.POLY] Chemical Sciences/Polymers ,Materials science ,Polymers and Plastics ,Radical polymerization ,02 engineering and technology ,Photothermal therapy ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Methacrylate ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,Electron transfer ,[CHIM.POLY]Chemical Sciences/Polymers ,Photopolymer ,Polymerization ,Materials Chemistry ,Irradiation ,Physical and Theoretical Chemistry ,Fourier transform infrared spectroscopy ,0210 nano-technology ,[SPI.SIGNAL]Engineering Sciences [physics]/Signal and Image processing ,[SPI.SIGNAL] Engineering Sciences [physics]/Signal and Image processing - Abstract
International audience; Polymerization of (meth)acrylate resins upon near‐infrared (NIR) light remains a huge challenge. In this study, a new photoinduced method of polymerization of methacrylic monomers is presented, originally merging a photochemical and a photothermal pathway. A four‐component system is proposed comprising an NIR dye combined with an iodonium salt, a phosphine, and a thermal initiator. A selection of dyes is suggested regarding electron transfer properties and/or light‐to‐heat conversion abilities. Several thermal initiators are studied: an alkoxyamine (BlocBuilder MA), an azo derivative, and a peroxide. For the first time, an NIR absorbing dye is used in photopolymerization using both its capacities of light‐to‐heat conversion and its ability to initiate an electron transfer reaction. Three wavelengths of irradiation will be presented here: 785, 940, and 1064 nm. These long wavelengths are challenging because the energy of photons is extremely low but these wavelengths offer significant advantages in term of light penetration (e.g., for the access to composites through photopolymerization processes). The different systems presented here exhibit high and rapid conversions of methacrylate functions. The underlying chemical mechanism will be fully depicted by real‐time Fourier transform infrared spectroscopy and thermal imaging measurements.
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- 2020
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12. Investigation of two-photon polymerized microstructures using fluorescence lifetime measurements
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Xingyu Wu, Mehdi Belqat, Benjamin Leuschel, Guillaume Noirbent, Frédéric Dumur, Karine Mougin, Arnaud Spangenberg, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Dumur, Frederic, ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), and ANR-16-CE08-0020,2PhotonInsight,Compréhension de la polymérisation biphotonique utilisée en écriture laser directe via la combinaison de différentes méthodes d'analyse résolues temporellement et spatialement(2016)
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[CHIM.POLY] Chemical Sciences/Polymers ,[CHIM.POLY]Chemical Sciences/Polymers ,Polymers and Plastics ,Organic Chemistry ,technology, industry, and agriculture ,Bioengineering ,macromolecular substances ,Biochemistry - Abstract
International audience; We report the use of fluorescence lifetime measurements for investigating two-photon polymerization. For this purpose, a molecular rotor was successfully exploited as a viscosity probe to reveal heterogeneity in multi-material microstructures made by two-photon polymerization. Furthermore, a correlation between laser intensity and local viscosity changes in the polymerized microstructures was established
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- 2022
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13. Substituent Effects on Photoinitiation Ability of Coumarin-Based Oxime-Ester Photoinitiators for Free Radical Photopolymerization
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Nicolas Giacoletto, Didier Gigmes, Guillaume Noirbent, Frédéric Dumur, Bernadette Graff, Fatima Hammoud, Akram Hijazi, Malek Nechab, Jacques Lalevée, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ecole Doctorale des Sciences et de la Technologie (EDST), Lebanese University [Beirut] (LU), 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), and Dumur, Frederic
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dual initiators ,Absorption spectroscopy ,Radical ,Radical polymerization ,Substituent ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,chemistry.chemical_compound ,Materials Chemistry ,General Materials Science ,Reactivity (chemistry) ,photoinitiators ,visible light ,[CHIM.MATE] Chemical Sciences/Material chemistry ,coumarins ,Chemistry ,[CHIM.MATE]Chemical Sciences/Material chemistry ,Chromophore ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Oxime-esters ,Photopolymer ,Polymerization ,0210 nano-technology - Abstract
International audience; In this paper, a series of coumarin chromophore-based oxime-esters was designed and synthesized as visible light photoinitiators (PIs). Interestingly, upon exposure to irradiation of a LED at 405 nm, the investigated oxime-esters (OXEs) could undergo a direct photocleavage, followed by decarboxylation, generating active free radicals capable to effectively initiate acrylate polymerization. Seven of the 10 investigated OXEs have never been synthesized in the literature. Markedly, the new proposed structures exhibit also thermal initiation ability and can be used as dual photo and thermal initiators. In addition, the oxime-ester system was also paired with an iodonium salt and exhibited a higher efficiency in free radical polymerization (FRP). The chemical mechanisms and the structure/reactivity/efficiency relationships were investigated through different techniques including real-time Fourier Transform Infrared Spectroscopy (RT-FTIR), UV-visible absorption spectroscopy, fluorescence (time-resolved or steady state), cyclic voltammetry as well as molecular modelling calculations. As a proof of their remarkable polymerization performance, the new OXEs were also used at 405 nm for direct laser write applications.
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- 2021
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14. Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 4,4-bis(4-methoxy phenyl)butadienyl donor
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Frédéric Dumur, Guillaume Noirbent, Corentin Pigot, Didier Gigmes, Thanh-Tuân Bui, Sébastien Péralta, Malek Nechab, Sylvain Duval, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), CY Cergy Paris Université (CY)-CY Cergy Paris Université (CY), Ecole Nationale Supérieure de Chimie de Lille (ENSCL), Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), and Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille
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chemistry.chemical_classification ,Absorption spectroscopy ,010405 organic chemistry ,Chemistry ,Process Chemistry and Technology ,General Chemical Engineering ,Solvatochromism ,solvatochromism ,indanedione ,TNF ,TCF ,[CHIM.MATE]Chemical Sciences/Material chemistry ,Electron acceptor ,010402 general chemistry ,Photochemistry ,Electrochemistry ,01 natural sciences ,Push-pull dyes ,Michler's aldehyde ,0104 chemical sciences ,Solvent ,Polarizability ,rhodanine ,Absorption (chemistry) ,Cyclic voltammetry - Abstract
International audience; A series of twelve dyes based on the 4,4-bis(4-methoxyphenyl)butadienyl donor and differing by the electron acceptors have been designed and synthesized. The different dyes were characterized by UV-visible absorption spectroscopy as well as cyclic voltammetry. By fine tuning the electron-accepting ability of the fourteen selected acceptors, dyes absorbing between 400 and 650 nm could be obtained with this π-extended donor. To get a deeper insight into the optical properties, solvatochromism was investigated in 23 different solvents and remarkable linear correlations could be obtained using the Taft and Catalan solvatochromism scales. A comparison with four dyes used as reference compounds and differing from the series of twelve dyes by the structure of the electron-donating groups was also established so that the electron releasing ability of the 4,4-bis(4-methoxyphenyl)butadienyl donor could be compared with the reference ones. To prepare these four references compounds, only two electron acceptors previously used for the design of the twelve dyes have been employed. Interestingly, variation of the absorption maxima of the twelve dyes was determined as being more influenced by the polarizability of the solvent rather than by its polarity. To support the experimental results, theoretical calculations were carried out.
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- 2021
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15. Different NIR dye scaffolds for polymerization reactions under NIR light
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Aude Héloïse Bonardi, Jacques Lalevée, Didier Gigmes, Frédéric Dumur, Guillaume Noirbent, Fabrice Bonardi, Jean Pierre Fouassier, Céline Dietlin, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-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), 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), and Dumur, Frederic
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Materials science ,Polymers and Plastics ,Radical polymerization ,Bioengineering ,02 engineering and technology ,010402 general chemistry ,Methacrylate ,Photochemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,[CHIM]Chemical Sciences ,Cyanine ,ComputingMilieux_MISCELLANEOUS ,[CHIM.MATE] Chemical Sciences/Material chemistry ,Organic Chemistry ,Photothermal effect ,[CHIM.MATE]Chemical Sciences/Material chemistry ,021001 nanoscience & nanotechnology ,Porphyrin ,0104 chemical sciences ,Photopolymer ,chemistry ,Polymerization ,0210 nano-technology ,Phosphine - Abstract
WOS:000501007300010; In this article, near-infrared dyes of different structures have been investigated as new photoinitiators/photosensitizers for the free radical polymerization (FRP) of methacrylates upon Near InfraRed (NIR) light exposure using a laser diode @785 nm, @940 nm and @1064 nm. Interestingly, the use of squaraine, squarylium, boron-pyrromethene and porphyrin derivatives as efficient photoinitiators is clearly highlighted. These dyes are used in combination with an iodonium salt and a phosphine. Additionally, a thermal initiator can be added to the resin to take advantage of the photothermal effect, i.e., to the heat release during the polymerization process, so that polymerization kinetics could be greatly improved compared to the pure photochemical mode. These dyes can be proposed as alternatives to the well-established cyanine dyes, more commonly used for the photopolymerization of (meth)acrylates under NIR light.
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- 2019
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16. 3-Carboxylic Acid and Formyl-Derived Coumarins as Photoinitiators in Photo-Oxidation or Photo-Reduction Processes for Photopolymerization upon Visible Light: Photocomposite Synthesis and 3D Printing Applications
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Jacques Lalevée, Joumana Toufaily, Mahmoud Rahal, Tayssir Hamieh, Frédéric Dumur, Didier Gigmes, Bernadette Graff, Guillaume Noirbent, 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), Lebanese University [Beirut] (LU), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Dumur, Frederic, 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), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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Pharmaceutical Science ,Lalevée ,photocomposites ,02 engineering and technology ,Photochemistry ,01 natural sciences ,coumarin ,Analytical Chemistry ,M ,chemistry.chemical_compound ,DESIGN ,direct laser write ,Drug Discovery ,Noirbent ,ComputingMilieux_MISCELLANEOUS ,chemistry.chemical_classification ,free radical polymerization ,DERIVATIVES ,LEDS ,T ,Gigmes ,[CHIM.MATE]Chemical Sciences/Material chemistry ,021001 nanoscience & nanotechnology ,J. 3-Carboxylic Acid and Formyl-Derived Coumarins as Photoinitiators in Photo-Oxidation or Photo-Reduction Processes for Photopolymerization upon Visible Light: Photocomposite Synthesis and coumarin ,POLYMERIZATION ,Photopolymer ,Chemistry (miscellaneous) ,D ,Molecular Medicine ,Cyclic voltammetry ,0210 nano-technology ,Visible spectrum ,Carboxylic acid ,Radical polymerization ,Graff ,010402 general chemistry ,Article ,lcsh:QD241-441 ,lcsh:Organic chemistry ,G ,PHOTOCATALYSTS ,Physical and Theoretical Chemistry ,Hamieh ,[CHIM.MATE] Chemical Sciences/Material chemistry ,Acrylate ,Rahal ,Organic Chemistry ,Photodissociation ,LED ,J ,0104 chemical sciences ,B ,chemistry ,Polymerization ,Toufaily ,Dumur ,F - Abstract
In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical photopolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2) was also examined.
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- 2021
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17. Near-Infrared PhotoInitiating Systems: Photothermal Effect vs. Triplet-Triplet Annihilation -based UpConversion Polymerization
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Jacques Lalevée, Didier Gigmes, Aurore Caron, Guillaume Noirbent, Frédéric Dumur, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), 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), and Dumur, Frederic
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Materials science ,Free Radicals ,Polymers and Plastics ,Radical polymerization ,Near-Infrared Light ,Triplet-Triplet Annihilation ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,7. Clean energy ,01 natural sciences ,UpConversion ,Polymerization ,Materials Chemistry ,Fourier transform infrared spectroscopy ,[CHIM.MATE] Chemical Sciences/Material chemistry ,Organic Chemistry ,Photothermal effect ,Near-infrared spectroscopy ,Temperature ,[CHIM.MATE]Chemical Sciences/Material chemistry ,Photothermal therapy ,021001 nanoscience & nanotechnology ,Photon upconversion ,0104 chemical sciences ,Photopolymer ,0210 nano-technology - Abstract
International audience; NIR light induced polymerization has attracted more and more attention in the photopolymerization field due to the possibility to use safer and more penetrating wavelengths, reducing the hazardousness. Here, a novel perspective for the Free Radical Polymerization (FRP) of acrylate-based monomers based on Triplet-Triplet Annihilation UpConversion (TTA-UC) is proposed, avoiding the introduction of heavy metals, usually required in the TTA processes. Thermal imaging experiments and Real Time Fourier Transform Infrared (RT-FTIR) spectroscopy have been respectively used to record the temperature during NIR irradiation and measure the reactive function conversion. The competition between the TTA-UC and the NIR photothermal activation was investigated to compare the relative efficiency of both NIR processes. In view of the results obtained by the different methods, the photothermal effect seems to get the hupper hand over the photoactivation of the system.
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- 2021
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18. Triphenylamine-based aldehydes: Photoinitiators for multiphoton polymerization
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Frédéric Dumur, Dimitra Ladika, Areti Mourka, Guillaume Noirbent, David Gray, Didier Gigmes, and Maria Farsari
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chemistry.chemical_classification ,Benzaldehyde ,chemistry.chemical_compound ,Acrylate ,Aniline ,Photopolymer ,Polymerization ,chemistry ,Substituent ,Organic chemistry ,Triphenylamine ,Aldehyde - Abstract
Photopolymerization of (meth)acrylate-based formulations has become a widespread method for industry due to the high energy efficiency and low curing times of this technology. Various products from simple coatings to more complex applications such as additive manufacturing technologies are based on this versatile method. Common industrial radical photoinitiators are generally based on aromatic ketones. Benzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful; for instance in the preparation of various aniline dyes, perfumes, flavorings, and pharmaceutics. Parallel to this, triphenylamines are extensively used for the design of dyes used for solar energy conversion. In this work, three triphenylamine derivatives bearing formyl groups are as a new substance class of multi-photon lithography photoinitiators. The photophysical properties of the PIs were investigated by UV−Vis abs
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- 2021
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19. New Multifunctional Benzophenone-based Photoinitiators with High Migration Stability and the Application in 3D Printing
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Hong Chen, Damien Brunel, Jacques Lalevée, Fabrice Morlet-Savary, Guillaume Noirbent, Pu Xiao, Didier Gigmes, Shaohui Liu, Alexandre Mau, Bernadette Graff, Frédéric Dumur, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), Dumur, Frederic, 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)
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[CHIM.MATE] Chemical Sciences/Material chemistry ,Sulfonium ,Cationic polymerization ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,Hydrogen atom abstraction ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Photopolymer ,chemistry ,Polymerization ,Materials Chemistry ,Benzophenone ,Molecule ,General Materials Science ,0210 nano-technology ,Photoinitiator - Abstract
In this paper, seven new photoinitiators based on the benzophenone scaffold are specifically designed for photopolymerization under mild conditions upon light-emitting diode (LED) irradiation, i.e. four benzophenone-triphenylamine photoinitiators (denoted as BT1–BT4) and three benzophenone-carbazole photoinitiators (denoted as BC1–BC3). Noticeably, these structures have never been reported in the literature except for BT4, so these molecules have been specifically designed for photopolymerization applications. Remarkably, various combinations of chemical groups were investigated in this work to determine the effects of the substitution patterns on their photoinitiation abilities. The formation of benzophenone-triphenylamine and benzophenone-carbazole hybrid structures not only contributes to red-shift of the absorption maxima but also strongly enhances their molar extinction coefficients. The different compounds showed high photoinitiation abilities upon irradiation with an LED@405 nm, and the free radical photopolymerization of acrylates and the cationic polymerization of epoxides could be promoted with high final function conversions (e.g. 77% for the BT3/iodonium salt/amine system in free radical photopolymerization). Remarkably, these new PIs are also able to sensitize sulfonium salts upon irradiation @405 nm. Markedly, because of the benzophenone moiety, a monocomponent Type II PI behavior could be observed, e.g. these compounds could initiate the polymerization alone. Remarkably, benzophenone-triphenylamine compounds BT2, BT3 and BT4 exhibited better hydrogen abstraction abilities as Type II photoinitiators than the benchmark and commercial photoinitiator 2-isopropylthioxanthone in the absence of amines as well as in the presence of amines. Furthermore, the interaction between the photoinitiators and the different additives was investigated by steady state photolysis and fluorescence quenching experiments. The free radical generation in the BT3/amine system was confirmed by the electron spin resonance-spin trapping technique, and the chemical mechanisms related to the polymerization efficiency are discussed. In addition, the migration stability of BT3 was investigated, which was excellent due to its high molecular weight and its trifunctional character. Finally, the three-component photoinitiating system based on BT3 was successfully applied in 3D printing and the 3D patterns showed a good spatial resolution.
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- 2021
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20. NIR organic dyes as innovative tools for reprocessing/recycling of plastics: Benefits of the photothermal activation in the near-infrared range
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Guillaume Noirbent, Aurore Caron, Didier Gigmes, Jacques Lalevée, Valentin Launay, Frédéric Dumur, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-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), and Dumur, Frederic
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[CHIM.MATE] Chemical Sciences/Material chemistry ,Range (particle radiation) ,Materials science ,Nir light ,Near-infrared spectroscopy ,technology, industry, and agriculture ,Nanotechnology ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,Photothermal therapy ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,01 natural sciences ,0104 chemical sciences ,Electronic, Optical and Magnetic Materials ,Biomaterials ,Electrochemistry ,0210 nano-technology - Abstract
International audience; Photoinduced thermal polymerization upon Near-InfraRed (NIR) light has been recently reported in the literature as an efficient tool for polymer synthesis. In these different studies, a component capable to convert a NIR light into heat (called hereafter heater) was used in combination with a thermal initiator, promoting the Free-Radical Polymerization (FRP) of acrylate monomer. In this work, a completely different approach was developed since polymeric materials containing a very low amount of a stimuli-responsive compound were prepared by using a benchmark UV photoinitiator. As the stimuli-responsive compound, an
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- 2021
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21. Allyloxy ketones as efficient photoinitiators with high migration stability in free radical polymerization and 3D printing
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Guillaume Noirbent, Damien Brunel, Didier Gigmes, Zhaofu Ding, Yangyang Xu, Pu Xiao, Jacques Lalevée, Frédéric Dumur, Bernadette Graff, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), Dumur, Frederic, 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)
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chemistry.chemical_classification ,[CHIM.MATE] Chemical Sciences/Material chemistry ,Ketone ,Materials science ,Process Chemistry and Technology ,General Chemical Engineering ,Radical polymerization ,Cyclohexanone ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Monomer ,Photopolymer ,chemistry ,Amine gas treating ,Fourier transform infrared spectroscopy ,Trimethylolpropane ,0210 nano-technology - Abstract
Five ketone derivatives (ketone-1~ketone-5) never synthesized in the literature and containing the same peripheral 1,3-bis(allyloxy)benzene substituting group but different central cyclohexanone cores were designed and proposed as high-performance photoinitiators for the free radical polymerization of acrylates under mild conditions. In combination with an amine and an iodonium salt (Iod), these ketones could initiate the photopolymerization of di(trimethylolpropane) tetraacrylate (TA), a tetrafunctional acrylates monomer, upon visible LED irradiation at room temperature in both thick films (1.4 mm) and thin films (25 μm) conditions. The distinct photopolymerization profiles of acrylates were studied by real time Fourier transform infrared spectroscopy, which indicated that the ketone-2/amine/Iod system could induce the highest final conversion of acrylates in thick films condition, while ketone-5/amine/Iod system could induce the highest final conversion of acrylates in thin films condition. Photoreactivity of ketone-2 and ketone-5 was systematically investigated by steady state photolysis and fluorescence quenching experiments in the presence of an amine and an iodonium salt, respectively. Moreover, eminent migration stability of ketones in photocured TA was observed. Finally, the ketone-2 and ketone-5-based three-component photoinitiating systems were applied for the laser writing experiments of TA, and macroscopically tridimensional patterns were fabricated with an excellent spatial resolution.
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- 2021
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22. Bis-Chalcone Derivatives Derived from Natural Products as Near-UV/Visible Light Sensitive Photoinitiators for 3D/4D Printing
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Bernadette Graff, Pu Xiao, Didier Gigmes, Hong Chen, Guillaume Noirbent, Damien Brunel, Ke Sun, Jacques Lalevée, Yijun Zhang, Frédéric Dumur, Fabrice Morlet-Savary, Shaohui Liu, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), 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), Dumur, Frederic, and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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[CHIM.MATE] Chemical Sciences/Material chemistry ,Radical polymerization ,Cationic polymerization ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Photopolymer ,chemistry ,Ferrocene ,Pyridine ,photopolymerization ,Materials Chemistry ,Alkoxy group ,Thiophene ,General Materials Science ,Amine gas treating ,0210 nano-technology ,Reversible shape memory ,Bis-chalcones - Abstract
Four series of bis-chalcone compounds based on benzylpiperidinone, tetrahydrothiopyranone, pyridine or biphenyl central parts are designed and synthesized, enabling the development of ten bis-chalcones varying both by the central cores and by the substitution patterns (ortho, meta, para-positions) and the choice of the different groups attached to the peripheral substituents (alkoxy or allyloxy-substituted aromatic rings, thiophene, or ferrocene). In this series of ten bis-chalcones, eight of them were never synthesized before (i.e. only bis-chalcones 8 and 10 were already reported albeit never used as photoinitiators). These different dyes are proposed as new near-UV/visible light sensitive photoinitiators, in combination with an amine and an iodonium salt, to initiate the free radical photopolymerization (FRP) of PEG-diacrylate and the cationic photopolymerization (CP) of EPOX under LED@405 nm and LED@375 nm irradiation conditions. For the photopolymerization of acrylates carried out between thin films in laminate, all the bis-chalcones proposed in this work show higher photoinitiation abilities upon irradiation with a LED at 375 nm than at 405 nm, which is mainly due to their excellent light absorption properties in the near-UV region. Markedly, in contrast with the other two series of bis-chalcone compounds, pyridine-based bis-chalcones prove to be the most efficient photoinitiators, especially the bis-chalcones 5 and 9. Furthermore, all of them can also promote the cationic polymerization of epoxides upon LED irradiation at 375 nm, in the presence of an iodonium salt and an amine. More interestingly, some 3D patterns fabricated through the free radical polymerization of PEG-diacrylate demonstrate reversible swelling properties and shape-memory for access to 4D printing.
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- 2021
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23. Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5- trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor
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Didier Gigmes, Thanh-Tuân Bui, Malek Nechab, Frédéric Dumur, Sébastien Péralta, Corentin Pigot, Guillaume Noirbent, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), CY Cergy Paris Université (CY)-CY Cergy Paris Université (CY), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)
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Materials science ,Polarity (physics) ,General Chemical Engineering ,solvatochromism ,Electron donor ,02 engineering and technology ,010402 general chemistry ,Electrochemistry ,Photochemistry ,01 natural sciences ,chemistry.chemical_compound ,Claisen-Schmidt condensation ,Malononitrile ,chemistry.chemical_classification ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Process Chemistry and Technology ,Solvatochromism ,near infrared absorption ,visible absorption ,TCF ,Chromophore ,Electron acceptor ,021001 nanoscience & nanotechnology ,Acceptor ,Push-pull dyes ,0104 chemical sciences ,chemistry ,0210 nano-technology - Abstract
International audience; A series of chromophores was designed and synthesized using 2-(3-cyano-4,5,5-trimethylfuran-2 (5H)-ylidene) malononitrile (TCF) as the electron acceptor and differing from each other by the use of thirteen different electron donors. The different dyes were characterized for their optical and electrochemical properties and theoretical calculations were also carried out to support the experimental results. By changing the electron donor in the thirteen dyes, chromophores absorbing between 430 nm and 700 nm could be synthesized. Solvatochromism of the different dyes was analyzed in 23 solvents of different polarity and a positive solvatochromism was determined for all chromophores using the semi-empirical solvent polarity scales based on the Kamlet-Taft parameters (π *) or the Catalan parameters (SdP and SPP).
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- 2021
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24. Dyes with tunable absorption properties from the visible to the near infrared range : 2,4,5,7-tetranitrofluorene (TNF) as a unique electron acceptor
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Malek Nechab, Corentin Pigot, Frédéric Dumur, Guillaume Noirbent, Sébastien Péralta, Didier Gigmes, Thanh-Tuân Bui, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), CY Cergy Paris Université (CY)-CY Cergy Paris Université (CY), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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Materials science ,Absorption spectroscopy ,General Chemical Engineering ,solvatochromism ,TNF ,Electron donor ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,Electrochemistry ,01 natural sciences ,chemistry.chemical_compound ,chromophore ,mechanosynthesis ,Absorption (electromagnetic radiation) ,chemistry.chemical_classification ,Range (particle radiation) ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Process Chemistry and Technology ,Near-infrared spectroscopy ,Solvatochromism ,near infrared absorption ,Electron acceptor ,021001 nanoscience & nanotechnology ,Push-pull dyes ,0104 chemical sciences ,chemistry ,Knoevenagel reaction ,tetranitrofluorene ,0210 nano-technology - Abstract
International audience; Fourteen dyes based on 2,4,5,7-tetranitrofluorene (TNF) as the electron acceptor have been designed and prepared in a one-step synthesis. By modifying the electron donor, optical properties of the dyes could be efficiently tuned and an absorption ranging between 450 nm and 700 nm could be determined by UV-visible absorption spectroscopy. To get a deeper insight into the optical properties, solvatochromism of the fourteen dyes has also been examined. For all dyes, a positive solvatochromism was determined using different solvent polarity scales such as the Kamlet-Taft and the Catalan empirical scales. Finally, electrochemical properties were also examined, and a comparison of the electrochemical and optical bandgaps could be established. Theoretical calculations were also performed to characterize the different dyes.
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- 2021
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25. Photoinitiators of polymerization with reduced environmental impact: Nature as an unlimited and renewable source of dyes
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Guillaume Noirbent, Frédéric Dumur, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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natural product ,Polymers and Plastics ,Computer science ,General Physics and Astronomy ,Nanotechnology ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,Materials Chemistry ,cationic polymerization ,Environmental impact assessment ,visible light ,business.industry ,Free radical polymerization ,Organic Chemistry ,[CHIM.MATE]Chemical Sciences/Material chemistry ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Renewable energy ,Photopolymer ,Polymerization ,13. Climate action ,photopolymerization ,photoinitiator ,0210 nano-technology ,business - Abstract
International audience; The development of new procedures aiming at reducing the environmental impact of polymerization processes is a major societal issue. In this field, light-assisted polymerization and especially visible light photopolymerization can address this issue by enabling in the future, Sun, to be used as the irradiation source. Presently, numerous visible light photoinitiators (xanthene dyes, porphyrins and phthalocyanines) are used in industry but their toxicities constitute a major issue for future uses of polymers. Therefore, photopolymerization is facing a short-term challenge and the development of visible light photoinitiators of polymerization has become a blooming field of research during the last decade. An ever-growing effort is thus done to develop new structures, effort which is also supported by the recent applications of photopolymerization in 3D-printing. Depending on the applications, use of synthetic photoinitiators can constitute a severe limitation for future applications of photopolymers so that the use of natural products has been identified as a promising alternative to address the toxicity or the biocompatibility issues. In this review, an overview of the different visible-light photoinitiators based on natural products is provided.
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- 2020
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26. Novel ketone derivatives based photoinitiating systems for free radical polymerization under mild conditions and 3D printing
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Guillaume Noirbent, Bernadette Graff, Didier Gigmes, Jacques Lalevée, Yangyang Xu, Frédéric Dumur, Zhaofu Ding, Damien Brunel, Pu Xiao, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), 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), Dumur, Frederic, and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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chemistry.chemical_classification ,Acrylate ,[CHIM.MATE] Chemical Sciences/Material chemistry ,Ketone ,Materials science ,Polymers and Plastics ,Organic Chemistry ,Radical polymerization ,Bioengineering ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry.chemical_compound ,Photopolymer ,chemistry ,Photosensitivity ,Polymerization ,Amine gas treating ,Trimethylolpropane ,0210 nano-technology - Abstract
Photopolymerization of acrylates under mild conditions is promising not only for academic research but also for industrial applications. However, it still remains a huge challenge to develop effective photoinitiators or photoinitiating systems for the free radical polymerization of acrylates under visible light-emitting diode (LED) irradiation. In this work, twelve novel ketone derivatives containing either tertiary amines or anthracenes as peripheral substituting groups (noted as Ami-1–Ami-6 and Anth-1–Anth-6) were elaborately synthesized and proposed for the polymerization of di(trimethylolpropane) tetraacrylate (TA), a tetrafunctional polyether acrylate, under both thin and thick film conditions under LED@405 nm irradiation. Remarkably, eight of the selected ketones (Ami-2, Ami-6, Anth-1–Anth-6) had never been synthesized before. In combination with an amine and/or an iodonium salt (Iod), these ketones could form distinct photoinitiating systems, among which the Ami-2/amine/Iod system could lead to the highest final conversion of acrylates under the thick film (∼1.4 mm) conditions while the Ami-6/amine/Iod system could induce the highest final conversion of acrylates under the thin film (∼25 μm) conditions. The photosensitivity of Ami-2 and Ami-6 was systematically investigated by steady state photolysis and fluorescence quenching experiments. Finally, the photocuring 3D printing technique was applied to TA, and both Ami-2- and Ami-6-based photoinitiating systems could be used to fabricate macroscopic 3D patterns with excellent spatial resolution.
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- 2020
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27. Recent Advances on Copper Complexes as Visible Light Photoinitiators and (Photo) Redox Initiators of Polymerization
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Guillaume Noirbent, Frédéric Dumur, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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TADF ,photosensitizer ,photoredox catalysis ,Radical polymerization ,chemistry.chemical_element ,02 engineering and technology ,lcsh:Chemical technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Redox ,Catalysis ,lcsh:Chemistry ,Mechanochemistry ,cationic polymerization ,lcsh:TP1-1185 ,Physical and Theoretical Chemistry ,copper complex ,free radical polymerization ,Cationic polymerization ,Photoredox catalysis ,[CHIM.MATE]Chemical Sciences/Material chemistry ,redox polymerization ,021001 nanoscience & nanotechnology ,Copper ,0104 chemical sciences ,Photopolymer ,lcsh:QD1-999 ,Polymerization ,chemistry ,photopolymerization ,photoinitiator ,0210 nano-technology - Abstract
International audience; Metal complexes are used in numerous chemical and photochemical processes in organic chemistry. Metal complexes have not been excluded from the interest of polymerists to convert liquid resins into solid materials. If iridium complexes have demonstrated their remarkable photochemical reactivity in polymerization, their high costs and their attested toxicities have rapidly discarded these complexes for further developments. Conversely, copper complexes are a blooming field of research in (photo) polymerization due to their low cost, easy syntheses, long-living excited state lifetimes, and their remarkable chemical and photochemical stabilities. Copper complexes can also be synthesized in solution and by mechanochemistry, paving the way towards the synthesis of photoinitiators by Green synthetic approaches. In this review, an overview of the different copper complexes reported to date is presented. Copper complexes are versatile candidates for polymerization, as these complexes are now widely used not only in photopolymerization, but also in redox and photoassisted redox polymerization processes.
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- 2020
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28. New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis
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Sébastien Péralta, Guillaume Noirbent, Sylvain Duval, Frédéric Dumur, Pierre-Henri Aubert, Thanh-Tuan Bui, Malek Nechab, Corentin Pigot, Didier Gigmes, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), and CY Cergy Paris Université (CY)-CY Cergy Paris Université (CY)
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chemistry.chemical_classification ,Process Chemistry and Technology ,General Chemical Engineering ,Aromatization ,02 engineering and technology ,[CHIM.MATE]Chemical Sciences/Material chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Aldehyde ,Medicinal chemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Nucleophile ,[CHIM]Chemical Sciences ,Knoevenagel condensation ,Amine gas treating ,Piperidine ,0210 nano-technology ,Derivative (chemistry) ,ComputingMilieux_MISCELLANEOUS ,Malononitrile - Abstract
International audience; A series of twelve dyes have been designed using 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-yli-dene)malononitrile as the electron acceptor. While using piperidine as a classical base for the Knoevenagel reaction , a nucleophilic attack of the amine on the formed push-pull chromophore occurred, producing an azaflu-orenone derivative. By varying the amine, a series of azafluorenones could be obtained. By using an aldehyde of extended conjugation, a spontaneous aromatization following the cyclization reaction could also be demonstrated. The optical, electrochemical properties of the different dyes were examined. Theoretical calculations were also carried out to support the experimental results.
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- 2020
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29. Recent advances on naphthalic anhydrides and 1,8-naphthalimide-based photoinitiators of polymerization
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Frédéric Dumur, Guillaume Noirbent, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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Research groups ,Materials science ,Polymers and Plastics ,low light intensity ,General Physics and Astronomy ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,naphthalic anhydride ,Materials Chemistry ,Naphthalic anhydride ,visible light ,Photoinitiator ,Organic Chemistry ,LED ,water-soluble ,021001 nanoscience & nanotechnology ,Combinatorial chemistry ,naphthalimide ,0104 chemical sciences ,Naphthalimides ,Light intensity ,Photopolymer ,[CHIM.POLY]Chemical Sciences/Polymers ,Polymerization ,panchromatic ,photopolymerization ,Visible range ,0210 nano-technology - Abstract
International audience; The design of photoinitiators of polymerization is an active research field and the development of initiators activable in the visible range and under low light intensity have been the focus of numerous research efforts from both the academic and industrial communities. Recently, two families of polyaromatic compounds, i.e. 1,8-naphthalic anhydride and naphthalimides, have been extensively studied by different research groups due to their easiness of synthesis and the possibility to easily tune the photophysical properties. Especially, panchromatic, crosslinkable or water-soluble photoinitiators could be easily developed starting from the benchmark and cheap 1,8-naphthalic anhydride. In this review, an overview of the different photoinitiators based on naphthalic anhydride or the naphthalimide scaffold is presented. Based on the diversity of structures reported in the literature, a structure-performance relationship could be established in this review.
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- 2020
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30. Metalated Porphyrins as versatile visible light and NIR photoinitiators of polymerization
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Frédéric Dumur, Aude-Héloise Bonardi, Guillaume Noirbent, Jacques Lalevée, Yangyang Xu, Didier Gigmes, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), 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), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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Materials science ,Polymers and Plastics ,NIR light ,Radical polymerization ,General Physics and Astronomy ,02 engineering and technology ,010402 general chemistry ,Methacrylate ,Photochemistry ,01 natural sciences ,chemistry.chemical_compound ,Materials Chemistry ,thermal initiator ,Solubility ,visible light ,free radical polymerization ,Organic Chemistry ,Photothermal therapy ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Light intensity ,Monomer ,[CHIM.POLY]Chemical Sciences/Polymers ,Polymerization ,chemistry ,photoinitiator ,0210 nano-technology ,porphyrin ,Visible spectrum - Abstract
International audience; A series of metalated porphyrins has been prepared and used as visible light photoinitiators of polymerization activable under low light intensity. Among the six metalated porphyrins examined in this work, five of them have never been reported in the literature and specifically designed to exhibit a good solubility in monomers. Three of the proposed structures were efficient @405nm but remarkably, despites their weak absorptions at 785 nm, efficient Near Infrared (NIR) polymerization profiles could also be obtained during the free radical polymerization of a methacrylate resin. To support the experimental observation of a polymerization process, a mechanism has been proposed based on combined photochemical and photothermal pathways.
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- 2020
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31. Ketone derivatives as photoinitiators for both radical and cationic photopolymerizations under visible LED and application in 3D printing
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Didier Gigmes, Shaohui Liu, Yijun Zhang, Ke Sun, Feiyang Liu, Guillaume Noirbent, Jacques Lalevée, Fabrice Morlet-Savary, Yangyang Xu, Frédéric Dumur, Pu Xiao, Damien Brunel, Anhui Normal University, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace, Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Strasbourg (UNISTRA)-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))-Université de Strasbourg (UNISTRA), Harbin Institute of Technology (HIT), 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), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Research School of Chemistry, Australian National University (ANU), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), 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), and Dumur, Frederic
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[CHIM.POLY] Chemical Sciences/Polymers ,Ketone ,Polymers and Plastics ,ketones ,Radical polymerization ,General Physics and Astronomy ,Cyclohexanone ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Polymer chemistry ,Materials Chemistry ,Thiophene ,cationic polymerization ,chemistry.chemical_classification ,Acrylate ,free radical polymerization ,Chemistry ,Organic Chemistry ,LED ,Cationic polymerization ,3D printing ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Photopolymer ,[CHIM.POLY]Chemical Sciences/Polymers ,Polymerization ,photolysis ,photoinitiating system ,0210 nano-technology ,cyclohexanone - Abstract
International audience; Six ketones (abbreviated as ketones 1-6) varying by the substitution pattern of the central cyclohexanones and the choice of the peripheral groups (thiophene or furane) were synthesized and proposed as unprecedented visible light sensitive photoinitiators, in combination with an amine and an iodonium salt, for the free radical polymerization of acrylates upon LED irradiation at 405 nm. For the photopolymerization of acrylates carried out as thin samples in laminate, all these ketones showed high photoinitiating abilities. Conversely, when tested as photoinitiators for thick samples, compared to the other 4 ketones, ketone 3 and ketone 5 both based onpiperidin-4-one as the central core and comprising furanes as peripheral groups proved to be the most efficient photoinitiators. Notably, the highest final polymerization conversion of Ebecryl 40, a tetrafunctional polyether acrylate, could be obtained using these two photoinitiators. The high photoreactivity of ketone 3 was highlighted by the steady state photolysis experiments. Meanwhile, ketone 3 could also promote the cationic polymerization of epoxides upon LED irradiation at 405 nm, in the presence of an iodonium salt. Interestingly, some 3D patterns could also be fabricated by free radical polymerization of Ebecryl 40 while using the ketone 3-based photoinitiating system.
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- 2020
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32. The new LED-Sensitive photoinitiators of Polymerization: Copper complexes in free radical and cationic photoinitiating systems and application in 3D printing
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Jacques Lalevée, Timur Borjigin, Didier Gigmes, Frédéric Dumur, Guillaume Noirbent, and Pu Xiao
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chemistry.chemical_classification ,Polymers and Plastics ,Spin trapping ,Organic Chemistry ,Radical polymerization ,Cationic polymerization ,General Physics and Astronomy ,02 engineering and technology ,Polymer ,TMPTA ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Monomer ,chemistry ,Polymerization ,Materials Chemistry ,Fourier transform infrared spectroscopy ,0210 nano-technology - Abstract
A ligand (A1) and four copper complexes (Cu1, Cu2, Cu3 and Cu4) were examined as photosensitizers in various photoinitiating systems (PISs). Interestingly, excellent photochemical reactivities were determined with the different compounds. Especially, notable photoinitiation abilities were determined upon exposure to LED@405 nm during the free radical polymerization of acrylates and the cationic polymerization of epoxides when combined with an iodonium salt and an amine. With regards to their remarkable reactivities, the different photoinitiating systems were applied to 3D printing experiments. By combining steady state photolysis and electron spin resonance spin trapping, the chemical mechanism supporting the polymerization processes could be fully detailed and proved. Among all PISs studied, the three-component PISs furnished the best monomer conversions during the free radical polymerization of trimethylolpropane triacrylate (TMPTA) and the cationic polymerization of (3,4-epoxycyclohexane)methyl 3,4-epoxycyclohexylcarboxylate (EPOX) monomers. The conversion process was monitored by real-time Fourier transform infrared spectroscopy (RT-FTIR). Three-component PISs based on A1, Cu1 and Cu2 showed better performances than those based on Cu3, Cu4 and the different two-component PIS (comprising only the iodonium salt or the amine) in FRP experiments. Based on the outstanding photoinitiation abilities of A1 and Cu1 with both TMPTA and EPOX, smooth and regular 3D patterns could be obtained by direct laser write experiments by generating interpenetrating polymer networks (IPN) with the blend of these two monomers.
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- 2022
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33. Unprecedented Nucleophilic Attack of Piperidine on the Electron Acceptor during the Synthesis of Push-Pull Dyes by a Knoevenagel Reaction
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Malek Nechab, Frédéric Dumur, Sylvain Duval, Corentin Pigot, Didier Gigmes, Sébastien Péralta, Guillaume Noirbent, Institut de Chimie Radicalaire (ICR), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU), Aix Marseille Université (AMU), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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electron acceptors ,Electron donor ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Biochemistry ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Nucleophile ,Drug Discovery ,electron donors ,[CHIM]Chemical Sciences ,piperidines ,Physical and Theoretical Chemistry ,Push pull ,chemistry.chemical_classification ,Chemistry ,Organic Chemistry ,Electron acceptor ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Knoevenagel reaction ,Knoevenagel condensation ,Piperidine ,0210 nano-technology ,push-pull systems - Abstract
WOS:000497883600001; International audience; An unprecedented nucleophilic addition of piperidine on an electron acceptor, namely, 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile is reported. This unexpected behavior was observed during the synthesis of push-pull dyes using the classical Knoevenagel reaction. To overcome this drawback, use of diisopropylethylamine (DIPEA) enabled to produce the expected dyes PP1 and PP2. The optical and electrochemical properties of the different dyes were examined. Theoretical calculations were also carried out to support the experimental results. To evidence the higher electron-withdrawing ability of this electron acceptor, a comparison was established with two dyes (PP3 and PP4) comprising its shorter analogue.
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- 2019
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34. Ferrocene-based (photo)redox polymerization under long wavelengths
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Jacques Lalevée, Fabrice Morlet-Savary, Valery F. Sidorkin, Frédéric Dumur, Bernadette Graff, Patxi Garra, David Duché, Damien Brunel, Jean-Pierre Fouassier, Céline Dietlin, Didier Gigmes, Guillaume Noirbent, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences (SB RAS), Institut des Matériaux, de Microélectronique et des Nanosciences de Provence (IM2NP), Aix Marseille Université (AMU)-Université de Toulon (UTLN)-Centre National de la Recherche Scientifique (CNRS), Gigmes, Didier, 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), and Université de Toulon (UTLN)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)
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[CHIM.POLY] Chemical Sciences/Polymers ,Polymers and Plastics ,Spin trapping ,Reducing agent ,Chemistry ,Radical ,Organic Chemistry ,Radical polymerization ,Photoredox catalysis ,Bioengineering ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,7. Clean energy ,01 natural sciences ,Biochemistry ,Redox ,0104 chemical sciences ,Photopolymer ,[CHIM.POLY]Chemical Sciences/Polymers ,Polymerization ,0210 nano-technology - Abstract
WOS:000462077800002 Electronic supplementary information (ESI) available: Fig. S1 and S2: synthesis of the different Fe complexes; Fig. S3: emission spectrum of LD@785 nm; Fig. S4: frontier molecular orbitals and UV-vis calculated spectra of the Fe complexes; Fig. S5: photopolymerization profiles upon LED@660 and 530 nm; Fig. S6: other redox polymerizations; Fig. S7: other; International audience; Ferrocene-based photoredox catalysis is proposed here for the first time. Aryl radicals generated from a Fe(II)*/Ar2I+ reaction can be used as initiating species for efficient free radical photopolymerization of methacrylate resins. Remarkably, these photoredox catalysts can also be used for redox free radical polymerization (without light) in combination with ammonium persulfate for unique access to dual cure (photochemical/thermal redox) systems. The addition of a third component (amine, phosphine or vitamin C reducing agents) enables the regeneration of the catalysts and greatly enhances the radical generation. The motivation with these dual cure systems is to develop orthogonal chemistries where a latent redox polymerization (without light) is able to cure any thickness of polymers (or composite) in combination with fast photopolymerization processes in the irradiated areas. Chemical mechanisms will be discussed in detail using cyclic voltammetry, electron spin resonance spin trapping (ESR-ST), UV-vis-NIR spectroscopy, free energy calculations and molecular modeling at the density functional theory (DFT) level. This study represents, to the best of our knowledge, the first photochemically active iron catalysts that are also efficient in thermal redox catalysis.
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- 2019
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35. Photopolymerization and 3D/4D applications using newly developed dyes: Search around the natural chalcone scaffold in photoinitiating systems
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Didier Gigmes, Fabrice Morlet-Savary, Guillaume Noirbent, Hong Chen, Shaohui Liu, Damien Brunel, Jacques Lalevée, Bernadette Graff, Ke Sun, Yijun Zhang, Pu Xiao, Frédéric Dumur, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), 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), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), and Dumur, Frederic
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[CHIM.MATE] Chemical Sciences/Material chemistry ,Reaction mechanism ,Chalcone ,Process Chemistry and Technology ,General Chemical Engineering ,Radical polymerization ,Cationic polymerization ,[CHIM.MATE]Chemical Sciences/Material chemistry ,02 engineering and technology ,Polyethylene glycol ,Natural dyes ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Photopolymer ,chemistry ,Hexafluorophosphate ,photopolymerization ,Polymer chemistry ,thermoresponsive and water-responsive reversible shape-memory ,Amine gas treating ,3D/4D printing ,0210 nano-technology - Abstract
Chalcones are well-known natural dyes, 18 different derivatives selected from the rational molecular design (i.e. through molecular orbital calculations) were synthesized. If used in conjunction with an amine (i.e. ethyl l, 4-(dimethylamino) benzoate, EDB) and an iodonium salt (bis(4-tert-butylphenyl) iodonium hexafluorophosphate, Iod) as photoinitiating systems (PISs), these dyes can initiate both the free radical polymerization of polyethylene glycol diacrylate (PEG-diacrylate) and the cationic polymerization of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (EPOX) via oxidation–reduction reaction mechanisms. Furthermore, among the 18 different suggested structures, except for dyes 9 and 10, which have been synthesized and used in other fields, the remaining 16 dyes have never been synthesized before. The photopolymerization efficiency of acrylates carried out under LED@405 nm are excellent both for thin films (the thickness is about 0.2 mm) and thick films (the thickness is about 2 mm). Furthermore, all of them can also boost the cationic polymerization of EPOX upon LED irradiation at 405 nm, in the presence of an iodonium salt and an amine. More interestingly, stereoscopic 3D patterns were successfully fabricated by the direct laser write (DLW) technique which demonstrated reversible swelling properties and reversible shape-memory effects induced via swelling and dehydration for the access to 4D printing.
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- 2021
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36. Monocomponent Photoinitiators based on Benzophenone-Carbazole Structure for LED Photoinitiating Systems and Application on 3D Printing
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Fabrice Morlet-Savary, Malek Nechab, Ke Sun, Shaohui Liu, Pu Xiao, Guillaume Noirbent, Damien Brunel, Yangyang Xu, Hong Chen, Jacques Lalevée, Frédéric Dumur, Didier Gigmes, Bernadette Graff, Yijun Zhang, Corentin Pigot, Institut de Science des Matériaux de Mulhouse (IS2M), 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 Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Australian National University (ANU), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017), 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), and Dumur, Frederic
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[CHIM.POLY] Chemical Sciences/Polymers ,Polymers and Plastics ,Substituent ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Article ,lcsh:QD241-441 ,chemistry.chemical_compound ,monocomponent photoinitiator ,lcsh:Organic chemistry ,carbazole ,Benzophenone ,Moiety ,Carbazole ,Cationic polymerization ,3D printing ,General Chemistry ,021001 nanoscience & nanotechnology ,3. Good health ,0104 chemical sciences ,[CHIM.POLY]Chemical Sciences/Polymers ,Photopolymer ,chemistry ,Polymerization ,0210 nano-technology ,Photoinitiator ,benzophenone - Abstract
In this article, different substituents (benzoyl, acetyl, styryl) are introduced onto the carbazole scaffold to obtain 8 novel carbazole derivatives. Interestingly, a benzoyl substituent, connected to a carbazole group, could form a benzophenone moiety, which composes a monocomponent Type II benzophenone-carbazole photoinitiator (PI). The synergetic effect of the benzophenone moiety and the amine in the carbazole moiety is expected to produce high performance photoinitiating systems (PISs) for the free radical photopolymerization (FRP). For different substituents, clear effects on the light absorption properties are demonstrated using UV-Visible absorption spectroscopy. Benzophenone-carbazole PIs can initiate the FRP of acrylates alone (monocomponent Type II photoinitiator behavior). In addition, fast polymerization rates and high function conversions of acrylate are observed when an amine and/or an iodonium salt are added in systems. Benzophenone-carbazole PIs have good efficiencies in cationic photopolymerization (CP) upon LED @ 365 nm irradiation in the presence of iodonium salt. In contrast, other PIs without synergetic effect demonstrate unsatisfied photopolymerization profiles in the same conditions. The best PIS identified for the free radical photopolymerization were used in three-dimensional (3D) printing. Steady state photolysis and fluorescence quenching experiments were carried out to investigate the reactivity and the photochemistry and photophysical properties of PIs. The free radicals, generated from the studied PISs, are detected by the electron spin resonance - spin trapping technique. The proposed chemical mechanisms are provided and the structure/reactivity/efficiency relationships are also discussed. All the results showed that the benzophenone-carbazole PIs have a good application potential, and this work provides a rational design route for PI molecules. Remarkably, BPC2-BPC4, C6, C8 were never synthetized before, therefore, 5 of the 8 compounds are completely new.
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- 2020
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37. Recent advances on push–pull organic dyes as visible light photoinitiators of polymerization
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Damien Brunel, Guillaume Noirbent, Corentin Pigot, Frédéric Dumur, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE08-0010,DUALITY,Elaboration de réseaux covalents bidimensionnels nanoporeux dirigés par la surface(2017), and ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
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chemistry.chemical_classification ,Materials science ,Polymers and Plastics ,Organic Chemistry ,General Physics and Astronomy ,Electron donor ,[CHIM.MATE]Chemical Sciences/Material chemistry ,02 engineering and technology ,Electron acceptor ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,Light intensity ,chemistry.chemical_compound ,Photopolymer ,chemistry ,Polymerization ,Intramolecular force ,Materials Chemistry ,Moiety ,0210 nano-technology ,Visible spectrum - Abstract
International audience; Photoinitiators activable under visible light and low light intensity are actively researched as it can advantageously address the safety concerns raised by the traditional UV-light photopolymerization process as well as the light penetration issue. Among dyes strongly absorbing in the visible range, one of the most promising family of photoinitiators are push-pull dyes based on an electron-donating and an electron-accepting moiety connected at both ends of a polyenyl-type spacer. By acting on both the strength of the electron donor and the electron accep-tor, position of the intramolecular charge transfer (ICT) band can be easily tuned from the near-UV to the near infrared region. In this review, an overview of the different D-π-A push-pull dyes used as visible photoinitiators of polymerization is presented. Over the years, a clear evolution in the chemical structure of the electron accep-tors can be clearly observed, evidencing the strong activity existing around these structures.
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- 2020
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38. Recent Advances on Nitrofluorene Derivatives: Versatile Electron Acceptors to Create Dyes Absorbing from the Visible to the Near and Far Infrared Region
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Guillaume Noirbent, Frédéric Dumur, Institut de Chimie Radicalaire (ICR), and Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
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Materials science ,Absorption spectroscopy ,Review ,Conjugated system ,Fluorene ,010402 general chemistry ,Photochemistry ,nitrofluorene ,01 natural sciences ,lcsh:Technology ,chemistry.chemical_compound ,fluorene ,Far infrared ,Molecule ,[CHIM]Chemical Sciences ,General Materials Science ,Absorption (electromagnetic radiation) ,lcsh:Microscopy ,push–pull chromophore ,poly(nitro)fluorene ,lcsh:QC120-168.85 ,chemistry.chemical_classification ,lcsh:QH201-278.5 ,010405 organic chemistry ,lcsh:T ,near infrared absorption ,Electron acceptor ,0104 chemical sciences ,chemistry ,Absorption band ,lcsh:TA1-2040 ,Knoevenagel reaction ,lcsh:Descriptive and experimental mechanics ,lcsh:Electrical engineering. Electronics. Nuclear engineering ,lcsh:Engineering (General). Civil engineering (General) ,lcsh:TK1-9971 - Abstract
WOS:000456419200083; Push-pull dyes absorbing in the visible range have been extensively studied so that a variety of structures have already been synthesized and reported in the literature. Conversely, dyes absorbing in the near and far infrared region are more scarce and this particularity relies on the following points: difficulty of purification, presence of side-reaction during synthesis, low availability of starting materials, and low reaction yields. Over the years, several strategies such as the elongation of the pi-conjugated spacer or the improvement of the electron-donating and accepting ability of both donors and acceptors connected via a conjugated or an aliphatic spacer have been examined to red-shift the absorption spectra of well-established visible dyes. However, this strategy is not sufficient, and the shift often remains limited. A promising alternative consists in identifying a molecule further used as an electron-accepting group and already presenting an absor ption band in the near infrared region and to capitalize on its absorption to design near and far infrared absorbing dyes. This is the case with poly(nitro)fluorenes that already exhibit such a contribution in the near infrared region. In this review, an overview of the different dyes elaborated with poly(nitro)fluorenes is presented. The different applications where these different dyes have been used are also detailed.
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- 2018
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39. Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region
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Jacques Lalevée, Frédéric Dumur, Guillaume Noirbent, Aude-Héloise Bonardi, Didier Gigmes, 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-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, 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)
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photoredox catalysis ,Nanotechnology ,Review ,010402 general chemistry ,01 natural sciences ,Polymer engineering ,Catalysis ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Microelectronics ,[CHIM]Chemical Sciences ,lcsh:Science ,chemistry.chemical_classification ,010405 organic chemistry ,business.industry ,Organic Chemistry ,Photoredox catalysis ,Polymer ,0104 chemical sciences ,Chemistry ,Photopolymer ,Monomer ,chemistry ,Polymerization ,photoredox catalyst ,photopolymerization ,lcsh:Q ,photoinitiator ,business - Abstract
WOS:000453278400001; Recent progresses achieved in terms of synthetic procedures allow now the access to polymers of well-defined composition, molecular weight and architecture. Thanks to these recent progresses in polymer engineering, the scope of applications of polymers is far wider than that of any other class of material, ranging from adhesives, coatings, packaging materials, inks, paints, optics, 3D printing, microelectronics or textiles. From a synthetic viewpoint, photoredox catalysis, originally developed for organic chemistry, has recently been applied to the polymer synthesis, constituting a major breakthrough in polymer chemistry. Thanks to the development of photoredox catalysts of polymerization, a drastic reduction of the amount of photoinitiators could be achieved, addressing the toxicity and the extractability issues; high performance initiating abilities are still obtained due to the catalytic approach which regenerates the catalyst. As it is a fast-growing field , this review will be mainly focused on an overview of the recent advances concerning the development of organic and organometallic photoredox catalysts for the photoreticulation of multifunctional monomers for a rapid and efficient access to 3D polymer networks.
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- 2018
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40. Photoinduced Thermal Polymerization Reactions
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Benoît H. Lessard, Trevor M. Grant, Jacques Lalevée, Didier Gigmes, Jean-Pierre Fouassier, Fabrice Morlet-Savary, Céline Dietlin, Fabien Bonardi, Frédéric Dumur, Aude-Héloise Bonardi, Guillaume Noirbent, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Science des Matériaux de Mulhouse (IS2M), 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), University of Ottawa [Ottawa], 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)
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Materials science ,Polymers and Plastics ,Organic Chemistry ,Radical polymerization ,technology, industry, and agriculture ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Wavelength ,Light intensity ,Monomer ,chemistry ,Polymerization ,Thermal ,Materials Chemistry ,[CHIM]Chemical Sciences ,Irradiation ,0210 nano-technology ,Curing (chemistry) - Abstract
WOS:000450694900050; The combination of thermally induced and photoinduced free radical polymerization of (meth)acrylic monomers has only been scarcely presented in the literature. In this study, a two-component system with a near- acts as a very efficient heat generator (heater) upon irradiation with NIR light. infrared (NIR) dye combined with a thermal initiator is presented. The dye Several thermal initiators are presented such as an alkoxyamine (e.g., BlocBuilder-MA), azo derivatives, and (hydro)peroxides. The heat delivered by the dye dissociates the thermal initiator, which initiates the free radical polymerization of (meth)acrylates. Several types of heat generators are presented such as borate-based dyes and a silicon phthalocyanine derivative. For the first time, the effects of the NIR heater concentration, light intensity, and monomer structure on the heat released are studied using thermal imaging studies. NIR light curing is challenging but offers significant advantage s: it is safer than shorter wavelength, and it allows a deeper penetration of the light and therefore a better curing of filled samples for a unique access to composites. Systems using a cyanine borate as a dye give high conversion rate of C=C for methacrylate monomer under air. Two wavelengths of irradiation are studied: 785 and 850 nm. The presence of additives (phosphines or iodonium salts) can also improve the polymerization profiles.
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- 2018
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41. Carbazole Derivatives with Thermally Activated Delayed Fluorescence Property as Photoinitiators/Photoredox Catalysts for LED 3D Printing Technology
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Tayssir Hamieh, Thanh-Tuan Bui, Jacques Lalevée, Bernadette Graff, Fabrice Goubard, Guillaume Noirbent, Diego Magaldi Lara, Joumana Toufaily, Assi Al Mousawi, Didier Gigmes, Frédéric Dumur, Jean Pierre Fouassier, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Sch Mech & Mat Engn, Pullman, WA 99164 USA, Washington State University (WSU), Lebanese University [Beirut] (LU), Laboratoire de Physico-chimie des Polymères et des Interfaces (LPPI), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Institut de Science des Matériaux de Mulhouse (IS2M), 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), Departement de Photochimie Générale, Ecole Nationale Supérieure de Chimie de Mulhouse (ENSCMu), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-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)-Aix Marseille Université (AMU), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-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 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)-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, 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), Ecole Nationale Supérieure de Chimie de Mulhouse, Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE), and 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
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Materials science ,Polymers and Plastics ,Carbazole ,Organic Chemistry ,Radical polymerization ,Substituent ,Cationic polymerization ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,Fluorescence ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Photopolymer ,Polymerization ,chemistry ,Polymer chemistry ,Materials Chemistry ,[CHIM]Chemical Sciences ,0210 nano-technology ,ComputingMilieux_MISCELLANEOUS ,Visible spectrum - Abstract
This paper is devoted to the effect of a thermally activated delayed fluorescence (TADF) property in new photoinitiators/photoredox catalysts. Four carbazole derivatives A1–A4 exhibiting a TADF character are synthesized and proposed for the first time as high performance visible light photoinitiators/metal-free photoredox catalysts, in the presence of an amine or/and an iodonium salt, for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides upon visible light exposure using light-emitting diodes (LEDs) at 405, 455, and 477 nm. Interestingly, the impact of the substituent effect on the excited state lifetimes and therefore on the photoinitiating ability of a series of substituted carbazoles was clearly evidenced and examined. Upon bromination of the carbazole core, clear effects on the excited state lifetimes and light absorption were demonstrated, enabling to tune the initiator performance. Excellent polymerization initiating abilities are found, a...
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- 2017
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42. Ferrocene: An unrivaled electroactive building block for the design of push-pull dyes with near-infrared and infrared absorptions
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Frédéric Dumur, Guillaume Noirbent, Damien Brunel, Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Aix Marseille Université (AMU)
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Materials science ,Infrared ,Process Chemistry and Technology ,General Chemical Engineering ,Near-infrared spectroscopy ,Nanotechnology ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Block (periodic table) ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Ferrocene ,chemistry ,[CHIM]Chemical Sciences ,0210 nano-technology ,Push pull - Abstract
WOS:000478711200061; International audience; Ferrocene is an exceptional building block for the development of dyes with reversible redox properties. Dyes absorbing int the near infrared and infrared region are actively researched due to their potential applications ranging from telecommunication to defence systems. In this review, an overview of the different NIR and infrared dyes reported to date is presented. Parallel to the photophysical characteristics, the synthetic pathways giving access to these structures is presented.
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- 2019
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43. A novel class of photoinitiators with a thermally activated delayed fluorescence (TADF) property
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Bouzrati-Zerelli, Mariem, primary, Guillaume, Noirbent, additional, Goubard, Fabrice, additional, Bui, Thanh-Tuan, additional, Villotte, Ségolène, additional, Dietlin, Céline, additional, Morlet-Savary, Fabrice, additional, Gigmes, Didier, additional, Fouassier, Jean Pierre, additional, Dumur, Frédéric, additional, and Lalevée, Jacques, additional
- Published
- 2018
- Full Text
- View/download PDF
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