title: Electrochemistry and reactivity of surface-confined catechol groups derived from diazonium reduction. Bias-assisted Michael addition at the solid/liquid interface.
abstract: We have designed a novel catechol-modified electrode that could be used for bias-assisted Michael addition at the solid/liquid interface. The glassy carbon electrode was modified by the electrochemical reduction of a catechol para-substituted phenyldiazonium salt. The electrochemistry of surface-confined catechol moieties was investigated by cyclic voltammetry. The transfer coefficient and apparent surface standard electron-transfer rate constant were obtained using Laviron's theory. We demonstrate that o-quinone moieties linked to the surface remain quite reactive with nucleophilic species by Michael addition at the solid/liquid interface. To demonstrate the versatility of this procedure, 4-nitrobenzyl alcohol, (4-nitrobenzyl)amine, and a ferrocenealkylamine were chosen as nucleophile models due to their well-known redox properties. Electrochemically triggered Michael addition was validated, leading to redox headgroup-tethered surfaces.
authors.affiliation: Unité de Chimie Organique Moléculaire et Macromoléculaire (UCO2M, UMR CNRS 6011), Université du Maine, Avenue O. Messiaen, F-72085 Le Mans Cedex 9, France.
authors.forename: Ngoc Hoa
authors.initials: NH
authors.lastname: Nguyen
authors.forename: Charles
authors.initials: C
authors.lastname: Esnault
authors.forename: Frédéric
authors.initials: F
authors.lastname: Gohier
authors.forename: Daniel
authors.initials: D
authors.lastname: Bélanger
authors.forename: Charles
authors.initials: C
authors.lastname: Cougnon