Butane-1,4-diyl dications stabilized by steric factors: Electrochiroptical response systems based on reversible interconversion between dihydro[5]helicene-type electron acceptors and electron-donating 1,1′-binaphthyls

Eisuke Ohta, Hiroki Higuchi, Hidetoshi Kawai, Kenshu Fujiwara, Takanori Suzuki

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27 Citations (Scopus)

Abstract

Incorporation in the dihydro[5]helicene framework prevents deprotonation of the title dications by steric factors, thus allowing their isolation as deeply colored stable salts. Based on the reversible interconversion with the electron-donating binaphthylic diolefins, they constitute a new class of electrochromic systems, in which C-C bond making/breaking is accompanied by two-electron transfer. Optically pure (R)-binaphthylic donors are interconvertible with the 1,4-dications with the R,R-configuration. The very large molar ellipticity makes it possible for them to be used as electrochiroptical response systems, by which the electrochemical input is transduced into two spectral outputs, i.e. UV-Vis and circular dichroism. Structurally related push-pull-type bis(quinonemethide)s also exhibit a similar multi-output electrochemical response.

Original languageEnglish
Pages (from-to)3024-3031
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number16
DOIs
Publication statusPublished - Aug 21 2005

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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