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Electrochemically grafted single molecule junctions exploiting a chemical protection strategy

Liang, Jinghong; Smith, Robert E.G.; Vezzoli, Andrea; Xie, Liqiang; Milan, David C.; Davidson, Ross; Beeby, Andrew; Low, Paul J.; Higgins, Simon J.; Mao, Bingwei; Nichols, Richard J.

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Authors

Jinghong Liang

Robert E.G. Smith

Andrea Vezzoli

Liqiang Xie

David C. Milan

Ross Davidson

Paul J. Low

Simon J. Higgins

Bingwei Mao

Richard J. Nichols



Abstract

Diazonium grafted oligo(phenylene ethynylene) (OPE) monolayers suitable for single molecule conductance studies have been prepared. The surface-bound OPE is prepared from the amino tolan, 4-(2-(4-(2-(triisopropylsilyl)ethynyl)phenyl)ethynyl)benzamine, which is converted to the diazonium derivative in situ, and subsequently attached to a gold substrate using conventional cathodic electrochemical grafting. Multilayer formation is avoided by the presence of the bulky triisopropylsilyl (TIPS) protected ethynyl group. After removal of the TIPS group by treatment with fluoride, the film, now bearing exposed terminal acetylene moieties, is further functionalised by reaction with 1-iodo-4-acetylthiobenzene using Sonogashira coupling chemistry, to create sites bearing a strongly aurophilic top-contacting group. The success of these surface reactions is confirmed using Raman spectroscopy (gap-mode and SHINERS, employing gold nanoparticles and SiO2 coated gold nanoparticles, respectively). It is shown that such thiolate-modified, diazonium-grafted monolayers are suitable for STM-based molecular junction conductance measurements.

Citation

Liang, J., Smith, R. E., Vezzoli, A., Xie, L., Milan, D. C., Davidson, R., …Nichols, R. J. (2016). Electrochemically grafted single molecule junctions exploiting a chemical protection strategy. Electrochimica Acta, 220, 436-443. https://doi.org/10.1016/j.electacta.2016.10.095

Journal Article Type Article
Acceptance Date Oct 15, 2016
Online Publication Date Oct 17, 2016
Publication Date Oct 17, 2016
Deposit Date Jun 18, 2019
Publicly Available Date Mar 28, 2024
Journal Electrochimica Acta
Print ISSN 0013-4686
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 220
Pages 436-443
DOI https://doi.org/10.1016/j.electacta.2016.10.095

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