Redox-dependent conformational switching of diphenylacetylenes

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

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)11316-11332
Number of pages17
JournalMolecules
Volume19
Issue number8
DOIs
StatePublished - Aug 2014

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • 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