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Published in

American Chemical Society, Journal of the American Chemical Society, 40(132), p. 14039-14041, 2010

DOI: 10.1021/ja106971x

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Efficient covalent modification of a carbon surface: use of a silyl protecting group to form an active monolayer.

Journal article published in 2010 by Yann R. Leroux, Hui Fei, Jean-Marc Noël, Clément Roux ORCID, Philippe Hapiot
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

A global strategy to prepare a versatile and robust reactive platform for immobilizing molecules on carbon substrates with controlled morphology and high selectivity is presented. The procedure is based on the electroreduction of a selected triisopropylsilyl (TIPS)-protected ethynyl aryldiazonium salt. It avoids the formation of multilayers and efficiently protects the functional group during the electrografting step. After TIPS deprotection, a dense reactive ethynyl aryl monolayer is obtained which presents a very low barrier to charge transfer between molecules in solution and the surface. As a test functionalization, azidomethylferrocene was coupled by "click" chemistry with the modified surface. Analysis of the redox activity highlights a surface concentration close to the maximum possible attachment considering the steric hindrance of a ferrocenyl group.