Synthesis, Structures, and Redox Behavior of Methyl-Substituted Derivatives of Thiophene-Inserted [3]Dendralene with Redox-Active 1,3-Dithiol-2-ylidene Units
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- Toshiki Ito
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
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- Masafumi Ueda
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
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- Masahiro Fujisaki
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
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- Aya Yoshimura
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
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- Takashi Shirahata
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
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- Yohji Misaki
- Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
Description
<jats:title>Abstract</jats:title> <jats:p>Several derivatives of 1,3-dithiole[3]dendralene with one thiophene spacer (1) were newly prepared. X-ray structure analysis of the hexamethyl-1 (1Aa) revealed that 1Aa adopts a structure with significant distortion between the central 1,3-dithiole (DT) ring and the thiophene ring. Cyclic voltammograms of all the derivatives were composed of three pairs of one-electron redox waves in correspondence with the presence of three redox-active DT rings. The results of cyclic voltammetry and spectroelectrochemistry indicated that a positive charge in 1Aa•+ is mainly delocalized on the vinyl-extended tetrathiafulvalene (TTF) moiety, while two positive charges in 1Aa2+ are mainly distributed on the thiophene-inserted TTF moiety. X-ray structure analysis revealed that two-electron oxidation of 1Aa with (4-BrC6H4)3N•+SbCl6− gradually facilitated the formation of a dicationic species of its chlorinated product.</jats:p>
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 95 (9), 1419-1427, 2022-07-29
Oxford University Press (OUP)
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Details 詳細情報について
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- CRID
- 1360579812037905024
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- ISSN
- 13480634
- 00092673
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- Article Type
- journal article
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- Data Source
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- Crossref
- KAKEN
- OpenAIRE
