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Updated: Jun 20, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
Published on: September 5, 2018
Electrochemistry and reactivity of surface-confined catechol groups derived from diazonium reduction. Bias-assisted
Ngoc Hoa Nguyen1, Charles Esnault, Frédéric Gohier
1Unité de Chimie Organique Moléculaire et Macromoléculaire (UCO2M, UMR CNRS 6011), Université du Maine, Avenue O. Messiaen, F-72085 Le Mans Cedex 9, France.
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.
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