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1. Influence of another, ruthenium containing, electroactive component on the apparent heterogeneous electron transfer rate constant of a ferrocene containing molecular wire in a Self-Assembled Monolayer of 11-hydroxyundecanethiol on gold

Author

Cédric Hortholary and Christophe Coudret

Subjects
General Chemical Engineering, chemistry.chemical_element, Self-assembled monolayer, General Chemistry, Photochemistry, Redox, Ruthenium, chemistry.chemical_compound, Electron transfer, Molecular wire, Reaction rate constant, chemistry, Ferrocene, Monolayer, Organic chemistry
Abstract

The co-adsorption of three thiol compounds on gold, two of them being electroactive, yields a Self-Assembled Monolayer (SAM) the behaviour of which was studied by impedance spectroscopy. The two redox active thiols have been chosen to have a good miscibility in a supporting inert component, non-degenerate first-oxidation redox couples, and distinct heterogeneous electron transfer rate constant. However, in the ternary monolayer, the slowest process was found to be concentration dependent on the other redox site. This unexpected behaviour should thus be taken into account when using multi-component SAM as a support for integrated devices.

Published
2008
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2. 'Electrical' Behavior of Photochromic Compounds

Author

Gonzalo Guirado, Christophe Coudret, Hubert Klein, Nicolas Battaglini, Jean-Pierre Launay, Cédric Hortholary, Ph. Dumas, Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre d'élaboration de matériaux et d'études structurales (CEMES), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Departament de Quimica, Universitat de Barcelona (UB), Interfaces, Traitements, Organisation et Dynamique des Systèmes (ITODYS (UMR_7086)), Université Paris Diderot - Paris 7 (UPD7)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Independent, Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA), Cinam, Hal, Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), and Centre National de la Recherche Scientifique (CNRS)-Université Paris Diderot - Paris 7 (UPD7)

Subjects
[PHYS]Physics [physics], 010405 organic chemistry, Chemistry, Analytical chemistry, Self-assembled monolayer, General Chemistry, 010402 general chemistry, Condensed Matter Physics, Ring (chemistry), Electrochemistry, Photochemistry, 01 natural sciences, Redox, 0104 chemical sciences, Photochromism, Molecular wire, Molecule, General Materials Science, ComputingMilieux_MISCELLANEOUS, Quantum tunnelling
Abstract

Dithienylethylene unit have been incorporated in a molecular wire. Incorporated in a Self Assembled Monolayer and tested by Scanning Tunnelling Microscopy, the molecule has been shown to have a blinking contrast. Redox properties of model compounds have been explored in order to explain this feature: all molecules can be oxidized and the resulting radical cations may undergo ring closure or opening depending on its substituents.

Published
2005
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3. Pentanuclear Cyanide-Bridged Complexes with High Spin Ground States S=6 and 9: Characterization and Magnetic Properties

Author

Guillaume Rogez, Cédric Hortholary, Talal Mallah, Jean-Paul Audière, Carley Paulsen, Vincent Villar, Arnaud Marvilliers, Eric Rivière, and Joan Cano Boquera

Subjects
Denticity, Spin states, chemistry.chemical_element, Crystal structure, Condensed Matter Physics, Magnetic susceptibility, Electronic, Optical and Magnetic Materials, Inorganic Chemistry, Nickel, Magnetization, Crystallography, Nuclear magnetic resonance, chemistry, Materials Chemistry, Ceramics and Composites, Antiferromagnetism, Physical and Theoretical Chemistry, Ground state
Abstract

Two pentanuclear complexes are obtained from the reaction of hexacyanochromate(III) with one to two molar equivalents of [Ni(H 2 O) 6 ] 2+ and bidentate organic ligands that chelate the metal ion, leaving two coordination sites in cis positions. Even though the crystal structure was not solved, the full characterization supports the formation of pentanuclear discrete species. [Cr(CN) 6 ] 2 [Ni(HIM2-py) 2 ] 3 ·7H 2 O, 1, has a ground spin state S=6 owing to the ferromagnetic interaction between Cr III ( S =3/2) and N II ( S =1). The presence of six organic radicals that couple ferromagnetically with Ni II in [Cr(CN) 6 ] 2 [Ni(IM2-py) 2 ] 3 ·7H 2 O, 2, leads to an S =9 ground state. A.c. susceptibility measurements below 2K indicate the occurrence of an antiferromagnetic order at 1.5 K in 2.

Published
2001
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4. STM observation of a single diarylethene flickering

Author

Christophe Coudret, Hubert Klein, Philippe Dumas, Nicolas Battaglini, François Maurel, Cédric Hortholary, Interfaces, Traitements, Organisation et Dynamique des Systèmes (ITODYS (UMR_7086)), Université Paris Diderot - Paris 7 (UPD7)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Centre de recherche de la matière condensée et des nanosciences (CRMCN), Université de la Méditerranée - Aix-Marseille 2-Université Paul Cézanne - Aix-Marseille 3-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Paris Diderot - Paris 7 (UPD7), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
02 engineering and technology, 010402 general chemistry, 01 natural sciences, Noise (electronics), law.invention, Electronic transport in nanoscale materials and structures, chemistry.chemical_compound, Diarylethene, law, Molecular conductance, Monolayer, Molecule, Scanning tunneling microscopy, Instrumentation, [PHYS]Physics [physics], Chemistry, Conductance, Self assembly, 021001 nanoscience & nanotechnology, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, 3. Good health, Electronic, Optical and Magnetic Materials, Self-assembly, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], Atomic physics, Scanning tunneling microscope, 0210 nano-technology
Abstract

International audience; We report the STM observation of single diarylethene derivatives (DD) embedded into alkylthiol Self Assembled Monolayers (SAM) on Au(111). Telegraph noise in the data shows that the molecular conductance oscillates between two states. Comparing our results to the ones obtained by other teams observing conductance flickering with systems in the same geometry, we relate the two observed states to the two isomeric configurations of the molecule under study.

Published
2007
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5. Three-centers models for electron transfer through a bridge. 1. Potential energy surfaces

Author

Christophe Coudret, Cédric Hortholary, and Jean-Pierre Launay

Subjects
Paraboloid, Chemistry, Diabatic, Geometry, Equilateral triangle, Potential energy, Surfaces, Coatings and Films, Reaction coordinate, Classical mechanics, Isosceles triangle, Materials Chemistry, Perpendicular, Physical and Theoretical Chemistry, Adiabatic process
Abstract

Three centers models adapted to the description of electron transfer through a bridge are discussed, with a special emphasis on potential energy surfaces. A short historical review of the available models is given, with a particular interest on the Bersuker-Borshch-Chibotaru model (1989) and the Lambert-Noll-Schelter model (2002). We propose our own model, inspired from the Bersuker-Borshch-Chibotaru model, but with a more physical discussion of the parameters and coordinates. The diabatic surfaces, before the intervention of electronic couplings between external site and bridge, consist of three revolution paraboloids of equal radii. The bottoms of the paraboloids do not form in general an equilateral triangle; they form an isosceles one. At this stage, the basic parameters are the ones describing the position of the third paraboloid (corresponding to a redox process on the bridge) with respect to the other two. We define in particular an energy shift parameter (Delta) and a depth parameter (d), the latter corresponding to the position of this paraboloid in the third dimension, i.e., along a coordinate of reaction perpendicular to the usual reaction coordinate. The topology of diabatic and adiabatic surfaces is discussed. As an application, we explain the contrasted behavior of two mixed valence systems bridged by anthracene and dimethoxybenzodithiophene, which differ by the value of the d parameter.

Published
2007

6. An Approach to Long and Unsubstituted Molecular Wires: Synthesis of Redox-Active, Cationic Phenylethynyl Oligomers Designed for Self-Assembled Monolayers

Author

Cédric Hortholary and and Christophe Coudret

Subjects
Stereochemistry, business.industry, Chemistry, Organic Chemistry, Cationic polymerization, chemistry.chemical_element, Self-assembled monolayer, General Medicine, Photochemistry, Oligomer, Ruthenium, chemistry.chemical_compound, Molecular wire, Semiconductor, Ferrocene, Hexafluorophosphate, Polymer chemistry, Redox active, Self-assembly, business
Abstract

Various oligo(phenyleneethynylene)s (OPEs) have been synthesized in the past, as they are considered as prototypes of molecular wires. When the oligomers are capped by a redox site at one end and a thiol at the other end, the resulting molecules can be grafted as a self-assembled monolayer on a gold electrode and fully studied by electrochemical techniques. Unfortunately, such molecules are usually poorly soluble and require the incorporation of solubilizing pendant groups. In this paper, we show that the replacement of the classically used redox group ferrocene by a cationic organometallic ruthenium complex, namely, [Ru(bipy)(2)(ppH)](+) (bipy, 2,2'-bipyridine; ppH, 2-(2'-yl-phenyl)pyridine), allows a concise synthesis of an unsubstituted thioacetate-capped OPE up to four repetitive units long. The positive charge does not interfere with the conventional organic chemistry used to elongate, purify, or characterize the hexafluorophosphate salts of the molecules. To our knowledge, this represents the first family of long, poorly substituted OPEs designed for self-assembly.

Published
2003
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7. A new redox site as an alternative to ferrocene to study electron transfer in self-assembled monolayers

Author

Cédric, Hortholary, Freddy, Minc, Christophe, Coudret, Jacques, Bonvoisin, and Jean-Pierre, Launay

Abstract

The cyclometallated ruthenium complex [Ru(bpy)2(pp)]+ (bpy: 2,2'-bipyridine; pp: 2-(2'-ylphenyl)pyridine) was easily grafted to a omega-alkanethiol and the resulting compound was coadsorbed with 11-hydroxyundecanethiol on gold yielding a Self-Assembled Monolayer (SAM) in an analogous manner as for a ferrocene derivative, as shown by impedance spectroscopy; the kinetics of the heterogeneous electron transfer were shown to be very fast, compared to ferrocene, which makes this new redox site a promising candidate for further studies about molecular wires.

Published
2002

8. A new redox site as an alternative to ferrocene to study electron transfer in self-assembled monolayersElectronic supplementary information (ESI) available: ac voltammograms, amount of redox active molecules determination, fitting law and SAM preparation protocol. See http://www.rsc.org/suppdata/cc/b2/b205073k

Author

Jacques Bonvoisin, Freddy Minc, Christophe Coudret, Jean-Pierre Launay, and Cédric Hortholary

Subjects
chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, Redox, Catalysis, chemistry.chemical_compound, Molecular wire, Electron transfer, Pyridine, Monolayer, Materials Chemistry, Metals and Alloys, Self-assembled monolayer, General Chemistry, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Ruthenium, chemistry, Ferrocene, Ceramics and Composites, 0210 nano-technology
Abstract

The cyclometallated ruthenium complex [Ru(bpy)2(pp)]+ (bpy: 2,2′-bipyridine; pp: 2-(2′-ylphenyl)pyridine) was easily grafted to a ω-alkanethiol and the resulting compound was coadsorbed with 11-hydroxyundecanethiol on gold yielding a Self-Assembled Monolayer (SAM) in an analogous manner as for a ferrocene derivative, as shown by impedance spectroscopy; the kinetics of the heterogeneous electron transfer were shown to be very fast, compared to ferrocene, which makes this new redox site a promising candidate for further studies about molecular wires.

Published
2002
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