Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 13, Issue 34, Pages 15624-15632Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1cp21450k
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Funding
- Australian research Council [DP01094564, DP0556397]
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A novel method to prepare redox monolayers on silicon electrodes has been developed that employs Cu-I-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 equivalent to C-C equivalent to 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.
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