Molecules (Jul 2014)

Redox-Dependent Conformational Switching of Diphenylacetylenes

  • Ian M. Jones,
  • Peter C. Knipe,
  • Thoe Michaelos,
  • Sam Thompson,
  • Andrew D. Hamilton

DOI
https://doi.org/10.3390/molecules190811316
Journal volume & issue
Vol. 19, no. 8
pp. 11316 – 11332

Abstract

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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.

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