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Oxidative acetylenic coupling reactions as a surface chemistry tool

Journal Article


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. This journal is © the Owner Societies.

Authors


  •   Ciampi, Simone (external author)
  •   James, Michael (external author)
  •   Darwish, Nadim A. (external author)
  •   Luais, Erwann (external author)
  •   Guan, Bin (external author)
  •   Harper, Jason Brian. (external author)
  •   Gooding, J Justin. (external author)

Publication Date


  • 2011

Citation


  • Ciampi, S., James, M., Darwish, N., Luais, E., Guan, B., Harper, J. B. & Gooding, J. Justin. (2011). Oxidative acetylenic coupling reactions as a surface chemistry tool. Physical Chemistry Chemical Physics, 13 (34), 15624-15632.

Scopus Eid


  • 2-s2.0-80052115255

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1836

Number Of Pages


  • 8

Start Page


  • 15624

End Page


  • 15632

Volume


  • 13

Issue


  • 34

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. This journal is © the Owner Societies.

Authors


  •   Ciampi, Simone (external author)
  •   James, Michael (external author)
  •   Darwish, Nadim A. (external author)
  •   Luais, Erwann (external author)
  •   Guan, Bin (external author)
  •   Harper, Jason Brian. (external author)
  •   Gooding, J Justin. (external author)

Publication Date


  • 2011

Citation


  • Ciampi, S., James, M., Darwish, N., Luais, E., Guan, B., Harper, J. B. & Gooding, J. Justin. (2011). Oxidative acetylenic coupling reactions as a surface chemistry tool. Physical Chemistry Chemical Physics, 13 (34), 15624-15632.

Scopus Eid


  • 2-s2.0-80052115255

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1836

Number Of Pages


  • 8

Start Page


  • 15624

End Page


  • 15632

Volume


  • 13

Issue


  • 34