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Communication | Special issue | Vol 90, No. 1, 2015, pp.136-143
Published online, 11th June, 2014
DOI: 10.3987/COM-14-S(K)33
Bis(diarylethenyl)thiophene, -bithiophene, and -terthiophene: A New Series of Violene-Cyanine Hybrid-Type Electron Donors

Yusuke Ishigaki, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, and Takanori Suzuki*

*Division of Chemistry, Graduate School of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan


The title fluorescent (oligo)thiophenes 1-3 were designed as new violene/cyanine-hybrid-type electron donors, which have two 4-methoxyphenyl groups each on the two cyanine parts. Voltammetric analyses showed that they all undergo reversible two-stage one-electron oxidation. The intramolecular short S(thiophene) -- Cipso(Ar) contacts were commonly present in their X-ray structures, and the coplanarily extended geometries are suitable for π-delocalization. Electrochemical oxidation of 1-3 caused continuous changes in their UV-Vis-NIR and fluorescence spectra although the oxidized species are too labile to be isolated.