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Electrochemical Functionalization of Carbon Surfaces by Aromatic Azide or Alkyne Molecules: A Versatile Platform for Click Chemistry
Author(s) -
Evrard David,
Lambert François,
Policar Clotilde,
Balland Véronique,
Limoges Benoît
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801168
Subject(s) - click chemistry , azide , alkyne , surface modification , chemistry , phenylacetylene , electrochemistry , acetylene , triazole , biomolecule , combinatorial chemistry , covalent bond , polymer chemistry , catalysis , photochemistry , organic chemistry , electrode , biochemistry
Abstract The electrochemical reduction of phenylazide or phenylacetylene diazonium salts leads to the grafting of azido or ethynyl groups onto the surface of carbon electrodes. In the presence of copper(I) catalyst, these azide‐ or alkyne‐modified surfaces react efficiently and rapidly with compounds bearing an acetylene or azide function, thus forming a covalent 1,2,3‐triazole linkage by means of click chemistry. This was illustrated with the surface coupling of ferrocenes functionalized with an ethynyl or azido group and the biomolecule biotin terminated by an acetylene group.