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Surfaces 2018, 1(1), 3-11; https://doi.org/10.3390/surfaces1010002

Switchable Interfaces: Redox Monolayers on Si(100) by Electrochemical Trapping of Alcohol Nucleophiles

1
School of Molecular and Life Sciences, Curtin Institute of Functional Molecules and Interfaces, Curtin University, Bentley, Western Australia 6102, Australia
2
ARC Centre of Excellence for Electromaterials Science, Intelligent Polymer Research Institute, University of Wollongong, Wollongong, New South Wales 2500, Australia
3
ARC Centre of Excellence for Electromaterials Science, Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory 2601, Australia
4
School of Chemistry, The University of New South Wales, Sydney, New South Wales 2052, Australia
*
Authors to whom correspondence should be addressed.
Received: 29 June 2018 / Accepted: 17 July 2018 / Published: 20 July 2018
(This article belongs to the Special Issue Electrochemical Surface Science: basics and applications)
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Abstract

Organic electrosynthesis is going through its renaissance but its scope in surface science as a tool to introduce specific molecular signatures at an electrode/electrolyte interface is under explored. Here, we have investigated an electrochemical approach to generate in situ surface-tethered and highly-reactive carbocations. We have covalently attached an alkoxyamine derivative on an Si(100) electrode and used an anodic bias stimulus to trigger its fragmentation into a diffusive nitroxide (TEMPO) and a surface-confined carbocation. As a proof-of-principle we have used this reactive intermediate to trap a nucleophile dissolved in the electrolyte. The nucleophile was ferrocenemethanol and its presence and surface concentration after its reaction with the carbocation were assessed by cyclic voltammetry. The work expands the repertoire of available electrosynthetic methods and could in principle lay the foundation for a new form of electrochemical lithography. View Full-Text
Keywords: electrosynthesis; switchable surfaces; alkoxyamine surfaces; redox monolayers electrosynthesis; switchable surfaces; alkoxyamine surfaces; redox monolayers
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Zhang, L.; Espíndola, R.B.D.; Noble, B.B.; Gonçales, V.R.; Wallace, G.G.; Darwish, N.; Coote, M.L.; Ciampi, S. Switchable Interfaces: Redox Monolayers on Si(100) by Electrochemical Trapping of Alcohol Nucleophiles. Surfaces 2018, 1, 3-11.

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