Redox-dependent conformational switching of diphenylacetylenes

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

*Corresponding author for this work

Research output: Contribution to journalArticle

10 Citations (Scopus)
177 Downloads (Pure)

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
Pages (from-to)11316-11332
Number of pages17
JournalMolecules
Volume19
Issue number8
DOIs
Publication statusPublished - 31 Jul 2014

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

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