Mixed azide-terminated monolayers: a platform for modifying electrode surfaces

Langmuir : the ACS Journal of Surfaces and Colloids
James P CollmanChristopher E D Chidsey

Abstract

We have prepared and characterized mixed self-assembled monolayers (SAM) on gold electrodes from azido alkane thiols and various omega-functionalized alkane thiols. In the presence of copper(I) catalysts, these azide-modified surfaces are shown to react rapidly and quantitatively with terminal acetylenes forming 1,2,3-triazoles, via "click" chemistry. The initial azide substituents can be identified and monitored using both grazing-angle infrared (IR) and X-ray photoelectron spectrosopies. Acetylenes possessing redox-active ferrocene substituents react with the azide-terminated mixed SAMs and electrochemical measurements of the ferrocene-modified SAM electrodes have been used to quantify the redox centers attached to these platforms. Time-resolved electrochemical measurements have enabled us to follow the formation of these ferrocene centers and thus to measure the rate of the surface "click" reaction. Under optimal conditions this well-behaved second-order reaction takes place with a rate constant of 1 x 10(3) M(-)(1) s(-)(1). Typical reaction times of several minutes were realized using micromolar concentrations of acetylene. These techniques have been used to construct well-characterized, covalently modified monolayers that ...Continue Reading

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Citations

Jul 20, 2006·Journal of the American Chemical Society·Rosemary D RohdeJames R Heath
Nov 3, 2010·Journal of the American Chemical Society·Guoting QinChengzhi Cai
Mar 4, 2011·Journal of the American Chemical Society·Charles C L McCroryChristopher E D Chidsey
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