Issue 34, 2011
From the journal:

Physical Chemistry Chemical Physics

Oxidative acetylenic coupling reactions as a surface chemistry tool†

Simone Ciampi,a   Michael James,ab   Nadim Darwish,a   Erwann Luais,a   Bin Guan,a   Jason B. Harpera  and  J. Justin Gooding*a  

* Corresponding authors

a School of Chemistry, The University of New South Wales, Sydney, Australia
E-mail: justin.gooding@unsw.edu.au
Fax: 61-2-9385 5384
Tel: 61-2-9385 6141

b Bragg Institute, Australian Nuclear Science and Technology Organisation (ANSTO), Locked Bag 2001, Kirrawee DC NSW 2232, Australia

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.

Graphical abstract: Oxidative acetylenic coupling reactions as a surface chemistry tool

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Article information

DOI
https://doi.org/10.1039/C1CP21450K
Article type
Paper
Submitted
06 May 2011
Accepted
08 Jul 2011
First published
29 Jul 2011

Phys. Chem. Chem. Phys., 2011,13, 15624-15632

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Oxidative acetylenic coupling reactions as a surface chemistry tool

S. Ciampi, M. James, N. Darwish, E. Luais, B. Guan, J. B. Harper and J. J. Gooding, Phys. Chem. Chem. Phys., 2011, 13, 15624 DOI: 10.1039/C1CP21450K

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