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    Oxidative acetylenic coupling reactions as a surface chemistry tool

    Access Status
    Fulltext not available
    Authors
    Ciampi, S.
    James, M.
    Darwish, Nadim
    Luais, E.
    Guan, B.
    Harper, J.
    Gooding, J.
    Date
    2011
    Type
    Journal Article
    
    Metadata
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    Citation
    Ciampi, S. and James, M. and Darwish, N. and Luais, E. and Guan, B. and Harper, J. and Gooding, J. 2011. Oxidative acetylenic coupling reactions as a surface chemistry tool. Physical Chemistry Chemical Physics. 13 (34): pp. 15624-15632.
    Source Title
    Physical Chemistry Chemical Physics
    DOI
    10.1039/c1cp21450k
    ISSN
    1463-9076
    School
    Nanochemistry Research Institute
    URI
    http://hdl.handle.net/20.500.11937/23997
    Collection
    • Curtin Research Publications
    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 (CC-CC-) 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.

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