Radical ions of alpha,alpha'-bis(diphenylamino)-capped oligothiophenes: a combined spectroelectrochemical and theoretical study

The Journal of Physical Chemistry. B
Dirk RohdeJürgen Fabian

Abstract

A new homologous series of alpha,alpha'-bis(diphenylamino)-capped oligothiophenes, prepared by a palladium-catalyzed coupling reaction of stannylated 2-diphenylaminothiophenes with 2-mono- or 2,5-dibromothiophenes and their homologues, was studied by in situ ESR/UV-vis/NIR spectroelectrochemistry. In general, the oxidation potentials of these oligothiophenes were found to be proportional to the inverse number of thiophene units. However, the potential slope of the first oxidation is completely different from that of higher oxidation steps. Trication radicals were identified by electron spin resonance (ESR) for higher thiophene homologues in addition to monocation radicals (polarons). According to the ESR hyperfine structures, the unpaired electron is delocalized in the conjugated system. In contrast to the parent alpha,alpha'-bis(diphenylamino)-capped oligothiophenes, the UV-vis/NIR absorption maxima of the oxidized species strongly depend on the number of thiophene units. Spin-restricted and spin-unrestricted Kohn-Sham density functional calculations were used to explain and to understand these properties. Absorption wavelength and intensities were calculated by the time-dependent density functional response theory. Unrestrict...Continue Reading

References

May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
May 16, 2002·Chemistry : a European Journal·Joke J ApperlooJean-Luc Brédas
Oct 25, 2003·The Journal of Organic Chemistry·Atsushi WakamiyaKoichi Komatsu
Jan 31, 2004·The Journal of Organic Chemistry·Zhong Hui LiMarie D'Iorio

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Citations

Sep 14, 2012·ACS Applied Materials & Interfaces·K M Nalin de SilvaEvgueni E Nesterov
Mar 8, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Peter RaptaLothar Dunsch
Nov 14, 2014·The Journal of Physical Chemistry. a·Ann Christin JahnkeOliver S Wenger
Feb 13, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Abdelaziz Al OuahabiSylvie Choua
Apr 8, 2010·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Olena YurchenkoSabine Ludwigs
Feb 9, 2007·Physical Chemistry Chemical Physics : PCCP·Agnieszka RogowskaBenoît Champagne
Jun 28, 2012·The Journal of Physical Chemistry. a·Luisa G ReuterOliver S Wenger
Sep 22, 2011·Journal of the American Chemical Society·Sandra R GonzálezJuan Casado
Aug 21, 2013·The Journal of Organic Chemistry·Tohru NishinagaMasahiko Iyoda
May 23, 2012·The Journal of Organic Chemistry·Yanmei DongW G Skene
Jun 26, 2007·The Journal of Physical Chemistry. B·Akira KumagaiTakakazu Yamamoto

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