Redox-dependent conformational switching of diphenylacetylenes

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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. 

LanguageEnglish
Pages11316-11332
Number of pages17
JournalMolecules
Volume19
Issue number8
DOIs
Publication statusPublished - 31 Jul 2014

Fingerprint

Oxidation-Reduction
switches
Switches
Fourier Analysis
Hydrogen Bonding
Cations
Oxidation
oxidation
Magnetic Resonance Spectroscopy
Electrons
Scaffolds
Nuclear magnetic resonance spectroscopy
Cyclic voltammetry
Hydrogen bonds
cations
nuclear magnetic resonance
Molecules
hydrogen
synthesis
spectroscopy

Keywords

  • Amide bond
  • Ferrocene
  • Hydrogen bonding
  • Molecular switch
  • Redox
  • Translational isomerism

Cite this

Jones, I. M., Knipe, P. C., Michaelos, T., Thompson, S., & Hamilton, A. D. (2014). Redox-dependent conformational switching of diphenylacetylenes. Molecules, 19(8), 11316-11332. https://doi.org/10.3390/molecules190811316
Jones, Ian M. ; Knipe, Peter C. ; Michaelos, Thoe ; Thompson, Sam ; Hamilton, Andrew D. / Redox-dependent conformational switching of diphenylacetylenes. In: Molecules. 2014 ; Vol. 19, No. 8. pp. 11316-11332.
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Jones, IM, Knipe, PC, Michaelos, T, Thompson, S & Hamilton, AD 2014, 'Redox-dependent conformational switching of diphenylacetylenes', Molecules, vol. 19, no. 8, pp. 11316-11332. https://doi.org/10.3390/molecules190811316

Redox-dependent conformational switching of diphenylacetylenes. / Jones, Ian M.; Knipe, Peter C.; Michaelos, Thoe; Thompson, Sam; Hamilton, Andrew D.

In: Molecules, Vol. 19, No. 8, 31.07.2014, p. 11316-11332.

Research output: Contribution to journalArticle

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Jones IM, Knipe PC, Michaelos T, Thompson S, Hamilton AD. Redox-dependent conformational switching of diphenylacetylenes. Molecules. 2014 Jul 31;19(8):11316-11332. https://doi.org/10.3390/molecules190811316