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 language | English |
|---|---|
| Pages (from-to) | 243-252 |
| Number of pages | 10 |
| Journal | Canadian Journal of Chemistry |
| Volume | 95 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Jan 1 2017 |
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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 journal › Article
}
TY - JOUR
T1 - Bis(diarylethenyl)-thiophenes,-bithiophenes, and-terthiophenes
T2 - A new series of electrochromic systems that exhibit a fluorescence response
AU - Ishigaki, Yusuke
AU - Kawai, Hidetoshi
AU - Katoono, Ryo
AU - Fujiwara, Kenshu
AU - Higuchi, Hiroki
AU - Kikuchi, Hirotsugu
AU - Suzuki, Takanori
PY - 2017/1/1
Y1 - 2017/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85014038331&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85014038331&partnerID=8YFLogxK
U2 - 10.1139/cjc-2016-0222
DO - 10.1139/cjc-2016-0222
M3 - Article
AN - SCOPUS:85014038331
VL - 95
SP - 243
EP - 252
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
SN - 0008-4042
IS - 3
ER -