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

AMA Style

Jones IM, Knipe PC, Michaelos T, Thompson S, Hamilton AD. Redox-Dependent Conformational Switching of Diphenylacetylenes. Molecules. 2014; 19(8):11316-11332.

Chicago/Turabian Style

Jones, Ian M., Peter C. Knipe, Thoe Michaelos, Sam Thompson, and Andrew D. Hamilton. 2014. "Redox-Dependent Conformational Switching of Diphenylacetylenes" Molecules 19, no. 8: 11316-11332.

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