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Molecules 2014, 19(8), 11316-11332; https://doi.org/10.3390/molecules190811316

Redox-Dependent Conformational Switching of Diphenylacetylenes

1
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK
2
Department of Chemistry, Yale University, P. O. Box 208107, New Haven, CT 06520-8107, USA
*
Authors to whom correspondence should be addressed.
Received: 28 April 2014 / Revised: 23 July 2014 / Accepted: 24 July 2014 / Published: 31 July 2014
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding)
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Abstract

Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch. View Full-Text
Keywords: molecular switch; ferrocene; hydrogen bonding; amide bond; redox; translational isomerism molecular switch; ferrocene; hydrogen bonding; amide bond; redox; translational isomerism
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Jones, I.M.; Knipe, P.C.; Michaelos, T.; Thompson, S.; Hamilton, A.D. Redox-Dependent Conformational Switching of Diphenylacetylenes. Molecules 2014, 19, 11316-11332.

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