Electrochemistry and reactivity of surface-confined catechol groups derived from diazonium reduction. Bias-assisted Michael addition at the solid/liquid interface.
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.
Nguyen
Ngoc Hoa
NH
Unité de Chimie Organique Moléculaire et Macromoléculaire (UCO2M, UMR CNRS 6011), Université du Maine, Avenue O. Messiaen, F-72085 Le Mans Cedex 9, France.
Esnault
Charles
C
Gohier
Frédéric
F
Bélanger
Daniel
D
Cougnon
Charles
C