Oxidative acetylenic coupling reactions as a surface chemistry tool
No Thumbnail Available
Date
2011-09-14
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
A novel method to prepare redox monolayers on silicon electrodes has been developed that employs CuI-catalyzed oxidative acetylenic coupling reactions for molecular electronic type applications. As the first case study, ethynylferrocene was covalently immobilized onto an acetylene-terminated monolayer on a Si(100) surface to give a 1,3-diyne (C[triple bond, length as m-dash]C-C[triple bond, length as m-dash]C-) linked redox assembly. The derivatization process requires no protection/de-protection steps, nor activation procedures. The effect of the conjugated diyne linkage on the rate of electron transfer between tethered ferrocenyl units and the silicon electrode is benchmarked against well-established "click" products (i.e. 1,2,3-triazole linkage). The surfaces, after each step, are characterized thoroughly using X-ray reflectivity (XRR), X-ray photoelectron spectroscopy (XPS), electrochemical impedance spectroscopy (EIS) and cyclic voltammetry (CV). The coupling chemistry provides a useful strategy for functionalizing silicon surfaces and contributes to an expanding repertoire of wet chemistry routes for the functionalization of solid substrates.© 2011, Royal Society of Chemistry
Description
Keywords
Silicon, X-ray photoelectron spectroscopy, Electrodes, Acetylene, Couplings, Solids
Citation
Ciampi, S., James, M., Darwish, N., Luais, E., Guan, B., Harper, J. B., & Gooding, J. J. (2011). Oxidative acetylenic coupling reactions as a surface chemistry tool. Physical Chemistry Chemical Physics, 13(34), 15624-15632. doi:10.1039/c1cp21450k