π-Donor layer coverage onto glassy carbon by electrochemical means. Reduction of ω-iodoalkyl-tetrathiafulvalenes

Lorcy, Dominique; Shin, Kyong-Soon; Guerro, Michel; Simonet, Jacques

doi:10.1016/j.electacta.2012.10.120

Cited by 9 publications

(4 citation statements)

References 28 publications

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“…31 The synthesis of the azido TTFs with different alkyl chains was realized starting from the corresponding iodo-alkyl-TTF according to published procedures (see Supporting Information). 32 Electrochemical Measurements. Electrochemical modification and characterization were performed with an Autolab PGSTAT N302 potentiostat/galvanostat (EcoChemie B.V.) equipped with the GPES software.…”

Section: Methodsmentioning

confidence: 99%

Tetrathiafulvalene-Tetracyanoquinodimethane Charge-Transfer Complexes Wired to Carbon Surfaces: Tuning of the Degree of Charge Transfer

et al. 2016

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International audienceCharge-transfer complexes involving tetrathiafulvalene (TTF) and tetracyanoquinodimethane (TCNQ) derivatives are engineered in a 2D arrangement onto a carbon surface through the exposure of immobilized TTF units to TCNQ compounds. TTF molecules were immobilized as robust monolayers on carbon surfaces using the electrografting method followed by a click chemistry coupling. When the TTF monolayer is exposed to TCNQ TCNQF(2) (2,5-difluoroTCNQ), and TCNQF4 (2,3,5,6-tetrafluoro-TCNQ), strong donor acceptor complexes are formed onto the surface. A considerable decrease of the electrochemical response accompanies the formation of the charge-transfer complex. This observation is rationalized by the analysis of original crystal samples using an ultramicroelectrode cavity, confirming that charge transfer complexes are electrochemically silent. A fine control of the degree of charge transfer with the judicious choice of different acceptors is evidenced through electrochemical and X-ray photoelectron spectroscopy (XPS) measurements. Thus, donor acceptor complexes of different natures are formed. A fully ionic charge-transfer complex is formed upon exposure of the TTF monolayer to the more oxidizing TCNQF(4), while a neutral complex is obtained after exposure to the less oxidizing TCNQ, Exposition of the TTF monolayers to the intermediate TCNQF(2) yields a mixture of neutral-ionic systems. These donor acceptor interactions that fully mimic those described in the solid state are rarely described in such a 2D arrangement, with systems being directly wired to an electrode

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Section: Methodsmentioning

confidence: 99%

Tetrathiafulvalene-Tetracyanoquinodimethane Charge-Transfer Complexes Wired to Carbon Surfaces: Tuning of the Degree of Charge Transfer

et al. 2016

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“…In other words, the GC surface could be perceived as a reactive material when quite negative potentials are reached (with active insertion stages [C n – , Alk 4 N + ] that can be seen as “graphite salts” similar to tetraalkylammonium amalgams and considered as both reducing species and polynucleophiles). This novel reactivity was recently used for covalent grafting of ferrocene and tetrathiafulvalene (TTF) to carbon surfaces using 1-iodoalkanes bearing corresponding redox active groups as precursors.…”

Section: Introductionmentioning

confidence: 99%

Efficient Anodic Allylation and Benzylation of Carbons Using Allyl and Benzyl Trimethylsilanes

Jouikov

Simonet

2013

Langmuir

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An easy process for allylation and benzylation of different carbon materials, primarily of glassy carbon, in acetonitrile solutions containing tetraalkyammonium salts is described. The method relies on the capability of C(sp(2)) zones of glassy carbon (graphite and fullerene-like inclusions) to be anodically charged at potentials >1.5 V versus Ag/AgCl to form electrophilic centers reacting with substituted trimethylsilanes RSiMe3. Great propensity of the trimethylsilyl group (TMS(+)) to act as a cationic leaving group facilitates electrophilic reactions of the charged anodic surface with R-carrying silylated precursors, permitting efficient grafting of a large variety of R groups. The present preliminary work focuses only on the efficient grafting of benzyl and allyl moieties.

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“…With this new method of immobilization at the GC surface, the grafting of redox active functionalities such as ferrocene and tetrathiafulvalenes was achieved by use of ω-iodoalkyl precursors. 23,24 Organometallic entities as well as π-donor moieties were used as redox probes to verify grafting reactions and to emphasize their efficiency. These processes may be of interest for developing electrocatalytic redox oxidation at the redox-decorated carbon surface, especially when such electrodes provide two reversible electron transfers.…”

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confidence: 99%

Electrochemical Cleavage of Alkyl Carbon-Halogen Bonds at Carbon-Metal and Metal-Carbon Substrates: Catalysis and Surface Modification

Jouikov¹,

Simonet²

2013

J. Electrochem. Soc.

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International audienceThe reaction of ferrocene-tagged primary alkyl iodides (RI) in polar aprotic solvents (dimethylformamide, acetonitrile, and propylene carbonate) in the presence of tetraalkylammonium salts was considered at several kinds of solid electrodes: (i) glassy carbon doped with sub-nanomolar layers of transition metals, graphite, and graphene, and (ii) gold and platinum modified by deposits of natural graphite and graphene. Under such conditions, extensive grafting of alkyl groups onto carbon (as substrate or as modifier) occurred, monitored using the redox response of ferrocene. Details of different modes of C-I bond cleavage at such interfaces are discussed

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π-Donor layer coverage onto glassy carbon by electrochemical means. Reduction of ω-iodoalkyl-tetrathiafulvalenes

Cited by 9 publications

References 28 publications

Tetrathiafulvalene-Tetracyanoquinodimethane Charge-Transfer Complexes Wired to Carbon Surfaces: Tuning of the Degree of Charge Transfer

Tetrathiafulvalene-Tetracyanoquinodimethane Charge-Transfer Complexes Wired to Carbon Surfaces: Tuning of the Degree of Charge Transfer

Efficient Anodic Allylation and Benzylation of Carbons Using Allyl and Benzyl Trimethylsilanes

Electrochemical Cleavage of Alkyl Carbon-Halogen Bonds at Carbon-Metal and Metal-Carbon Substrates: Catalysis and Surface Modification

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