Maleimide-Activated Aryl Diazonium Salts for Electrode Surface Functionalization with Biological and Redox-Active Molecules

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• 作者：Jason C. Harper ; Ronen Polsky ; David R. Wheeler ; Susan M. Brozik
• 刊名：Langmuir
• 出版年：2008
• 出版时间：March 4, 2008
• 年：2008
• 卷：24
• 期：5
• 页码：2206 - 2211
• 全文大小：146K
• 年卷期：v.24,no.5(March 4, 2008)
• ISSN：1520-5827

文摘

A versatile and simple method is introduced for formation of maleimide-functionalized surfaces using maleimide-activated aryl diazonium salts. We show for the first time electrodeposition of N-(4-diazophenyl)maleimidetetrafluoroborate on gold and carbon electrodes which was characterized via voltammetry, grazing angle FTIR, andellipsometry. Electrodeposition conditions were used to control film thickness and yielded submonolayer-to-multilayergrafting. The resulting phenylmaleimide surfaces served as effective coupling agents for electrode functionalizationwith ferrocene and the redox-active protein cytochrome c. The utility of phenylmaleimide diazonium toward formationof a diazonium-activated conjugate, followed by direct electrodeposition of the diazonium-modified DNA onto theelectrode surface, was also demonstrated. Effective electron transfer was obtained between immobilized moleculesand the electrodes. This novel application of N-phenylmaleimide diazonium may facilitate the development of bioelectronicdevices including biofuel cells, biosensors, and DNA and protein microarrays.