Electrochemical functionalization of carbon surfaces by aromatic azide or alkyne molecules: a versatile platform for click chemistry.
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.
Evrard
David
D
Laboratoire d'Electrochimie Moléculaire, UMR CNRS 7591, Université Paris Diderot, 2 place Jussieu, 75251 Paris cedex 05, France.
Lambert
François
F
Policar
Clotilde
C
Balland
Véronique
V
Limoges
Benoît
B
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D001360:Avidin / Q000737:chemistry / Q000378:metabolism; D001386:Azides / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D004563:Electrochemistry; D004566:Electrodes; D006735:Horseradish Peroxidase / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity; D013499:Surface Properties; D013997:Time Factors; D014867:Water / Q000737:chemistry
D001386:Azides; D003979:Diazonium Compounds; C093483:neutravidin; D014867:Water; D001360:Avidin; C044736:phenylacetylene; C014747:phenylazide; D001710:Biotin; D002244:Carbon; D006735:Horseradish Peroxidase; D000114:Acetylene