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Molecules 2014, 19(8), 11316-11332;

Redox-Dependent Conformational Switching of Diphenylacetylenes

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK
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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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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MDPI and ACS Style

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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