Selective functionalization of independently addressed microelectrodes by electrochemical activation and deactivation of a coupling catalyst

被引:159
作者
Devaraj, NK [1 ]
Dinolfo, PH [1 ]
Chidsey, CED [1 ]
Collman, JP [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja058380h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We demonstrate selective functionalization of independently addressed microelectrodes by electrochemical activation and deactivation of a coupling catalyst. 1,2,3-Triazole formation between terminal acetylenes and organic azides is efficiently catalyzed by copper(I) complexes (a Sharpless "click" reaction), while the oxidized copper(II) complexes are inactive. By electrochemically activating or deactivating the catalyst by switching its redox state, we demonstrate control over triazole formation between surface-immobilized azides and ethynylferrocene. The reaction proceeds on the time scale of minutes using submicromolar concentration of reactants and catalyst, requires mild potentials for catalyst activation and deactivation, and works in aqueous and mixed aqueous-organic solvents. By appropriate biasing of each electrode, we selectively modify one of two chemically identical 10-μm-wide electrodes separated by 10 μm in an interdigitated array. The ability to switch on or off the reaction by electrical addressing together with the chemoselectivity of this reaction makes Cu(I)-catalyzed triazole formation an ideal method for the chemical modification of multielectrode arrays. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1794 / 1795
页数:2
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