期刊
LANGMUIR
卷 22, 期 6, 页码 2457-2464出版社
AMER CHEMICAL SOC
DOI: 10.1021/la052947q
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资金
- NIGMS NIH HHS [GM-69568-01A1, R01 GM069658, L30 GM069568] Funding Source: Medline
We have prepared and characterized mixed self-assembled monolayers (SAM) on gold electrodes from azido alkane thiols and various -functionalized alkane thiols. In the presence of copper(l) 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 can be employed as functional electrode surfaces.
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