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Issue 16, 2005
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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

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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.

Graphical abstract: 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

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Supplementary files

Article information


Submitted
09 May 2005
Accepted
09 Jun 2005
First published
07 Jul 2005

Org. Biomol. Chem., 2005,3, 3024-3031
Article type
Paper

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

E. Ohta, H. Higuchi, H. Kawai, K. Fujiwara and T. Suzuki, Org. Biomol. Chem., 2005, 3, 3024
DOI: 10.1039/B506435J

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