Bis(diarylethenyl)-thiophenes,-bithiophenes, and-terthiophenes: A new series of electrochromic systems that exhibit a fluorescence response

Yusuke Ishigaki, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Hiroki Higuchi, Hirotsugu Kikuchi, Takanori Suzuki

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


2,5-Bis(diarylethenyl)thiophenes (1) and their bithiophene (2) and terthiophene (3) homologues were designed as a new series of violene/cyanine-hybrid-type electrochromic materials. Alkoxyphenyl and dialkylaminophenyl groups are used as the aryl group in the cyanine parts of 1/2/3O and 1/2/3N, respectively, which emit fluorescence in the neutral state but not in the oxidized state. Voltammetric analyses of 18 newly prepared electron donors show that they all undergo two reversible one-electron oxidations. Redox potentials, UV-vis spectral features, and fluorescence quantum yields are important parameters for characterizing the present electrochromic behavior with a fluorescence response, and can be finely tuned by changing aryl groups in the cyanine part, the number of thiophene rings in the violene part, and the alkyl-chain length of the alkoxyphenyl or diaklylaminophenyl groups (R = CH3, C8H17, C16H33), which makes this a versatile platform for the design of novel electrochromic materials.

Original languageEnglish
Pages (from-to)243-252
Number of pages10
JournalCanadian Journal of Chemistry
Issue number3
Publication statusPublished - 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Organic Chemistry


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