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Impact of the Diazonium Grafting Control on the Interfacial Reactivity: Monolayer versus Multilayer
Author(s) -
Menanteau Thibaud,
DabosSeig Sylvie,
Levillain Eric,
Breton Tony
Publication year - 2017
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201600710
Subject(s) - monolayer , reactivity (psychology) , surface modification , electron transfer , chemistry , electrochemistry , grafting , covalent bond , redox , combinatorial chemistry , molecule , nanotechnology , self assembled monolayer , photochemistry , materials science , organic chemistry , electrode , medicine , alternative medicine , pathology , polymer
A very simple strategy to prepare, in two steps, a versatile and sustainable monolayer platform for on‐surface chemistry is presented. The first step consists of the electroreduction of well‐known 4‐nitrobenzenediazonium in the presence of a radical scavenger, leading to a covalent monolayer surface modification. Then, a dense reactive phenylamine monolayer is obtained through the full electroreduction of the nitrophenyl moieties. The platform thus obtained is available for post‐functionalization with carboxyl derivatives through a usual peptide coupling. Attachment of a TEMPO unit, offering both redox and electrocatalytic properties, validates this approach and leads to high surface coverage and fast electron transfer. A comparison of the electrochemical properties of the modified surface with a classical multilayered post‐functionalized one highlights important differences in terms of interfacial reactivity. The results presented here justify the interest in preparing a reactive monolayer platform for molecule grafting and paves the way for simple and controlled surface chemistry without the need of synthesis.