title: Electrochemical immobilization of a benzylic film through the reduction of benzyl halide derivatives: deposition onto highly ordered pyrolytic graphite.
abstract: The reactivity of electrogenerated benzyl radicals at carbon surfaces was examined through the cathodic reduction of the corresponding bromide derivatives. 4-Nitrobenzyl bromide and benzyl bromide were reduced in N,N-dimethylformamide (DMF) on highly ordered pyrolytic graphite (HOPG) surfaces. Electroproduced films were examined using electrochemistry, scanning electron microscopy (SEM), and atomic force microscopy (AFM). Experiments show the formation of strongly adherent deposits and the occurrence of electrografting processes. They are based on radical generation and the reaction of the radical with the substrate. As expected, the thickness of the organic film increases with deposition time but the deposit displays a lower compactness than previously reported for the electroreduction of aryl diazonium salts. Interestingly for benzyl derivatives, the reduction potential required for the electrografting could be rendered much more positive by simply using an iodide-type supporting electrolyte.
authors.affiliation: Sciences Chimiques de Rennes (Equipe MaCSE), CNRS, UMR 6226, Université de Rennes 1, Campus de Beaulieu, Bat 10C, 35042 Rennes Cedex, France.
authors.forename: Fei
authors.initials: F
authors.lastname: Hui
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Noël
authors.forename: Philippe
authors.initials: P
authors.lastname: Poizot
authors.forename: Philippe
authors.initials: P
authors.lastname: Hapiot
authors.forename: Jacques
authors.initials: J
authors.lastname: Simonet
mesh_terms: D000327:Adsorption; D001593:Benzyl Compounds / Q000737:chemistry*; D055664:Electrochemical Techniques; D006108:Graphite; D010084:Oxidation-Reduction
chemical_list: D001593:Benzyl Compounds; D006108:Graphite; C038682:benzyl bromide