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 journalArticle

1 Citation (Scopus)

Abstract

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
Volume95
Issue number3
DOIs
Publication statusPublished - Jan 1 2017

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Thiophenes
Thiophene
Fluorescence
Electrons
Quantum yield
Chain length
Oxidation
alpha-terthienyl

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Bis(diarylethenyl)-thiophenes,-bithiophenes, and-terthiophenes : A new series of electrochromic systems that exhibit a fluorescence response. / Ishigaki, Yusuke; Kawai, Hidetoshi; Katoono, Ryo; Fujiwara, Kenshu; Higuchi, Hiroki; Kikuchi, Hirotsugu; Suzuki, Takanori.

In: Canadian Journal of Chemistry, Vol. 95, No. 3, 01.01.2017, p. 243-252.

Research output: Contribution to journalArticle

Ishigaki, Yusuke ; Kawai, Hidetoshi ; Katoono, Ryo ; Fujiwara, Kenshu ; Higuchi, Hiroki ; Kikuchi, Hirotsugu ; Suzuki, Takanori. / Bis(diarylethenyl)-thiophenes,-bithiophenes, and-terthiophenes : A new series of electrochromic systems that exhibit a fluorescence response. In: Canadian Journal of Chemistry. 2017 ; Vol. 95, No. 3. pp. 243-252.
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