Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: Synthesis, photophysical and electrochemical properties, and self-assembly behavior

Shin Ichiro Kato, Satoshi Jin, Terutaka Kimura, Naoki Yoshikawa, Daiki Nara, Kenji Imamura, Yoshihito Shiota, Kazunari Yoshizawa, Ryo Katoono, Takeshi Yamanobe, Hiroki Uehara, Yosuke Nakamura

研究成果: ジャーナルへの寄稿記事

4 引用 (Scopus)

抄録

We report the synthesis, photophysical properties, redox characteristics, and self-assembly behavior of disk-shaped trithiazolyl-1,3,5-triazines that bear decyloxybenzene moieties. These compounds were synthesized by a Migita-Kosugi-Stille coupling reaction of 1,3,5-trichlorotriazine with three different tributyltin(thiazoles) as the key step. The structure-property relationships, namely the effects of the incorporation of thiazole units into the triazine unit, the conjugation connectivity between the thiazole and triazine units, and the insertion of ethynylene spacers between the thiazole and decyloxybenzene moieties on the properties of the trithiazolyl-1,3,5-triazines were comprehensively investigated. Binding of the triazine core at the 5-position of the thiazole moieties effectively extended the π-conjugation and afforded high fluorescence quantum yields. The ethynylene spacers substantially lowered the LUMO level relative to the HOMO level. The prepared trithiazolyl-1,3,5-triazines self-assembled in solution, and the introduction of thiazole units at the 5-position enhanced this behavior. Detailed thermodynamic studies on the self-association behavior were conducted, and the formation of self-assembled 1D clusters is disclosed.

元の言語英語
ページ(範囲)3584-3595
ページ数12
ジャーナルOrganic and Biomolecular Chemistry
16
発行部数19
DOI
出版物ステータス出版済み - 1 1 2018

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Bearings (structural)
Thiazoles
Triazines
Electrochemical properties
Self assembly
self assembly
conjugation
spacers
synthesis
bears
insertion
fluorescence
thermodynamics
Quantum yield
Thermodynamics
Oxidation-Reduction
Fluorescence
Association reactions

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties : Synthesis, photophysical and electrochemical properties, and self-assembly behavior. / Kato, Shin Ichiro; Jin, Satoshi; Kimura, Terutaka; Yoshikawa, Naoki; Nara, Daiki; Imamura, Kenji; Shiota, Yoshihito; Yoshizawa, Kazunari; Katoono, Ryo; Yamanobe, Takeshi; Uehara, Hiroki; Nakamura, Yosuke.

:: Organic and Biomolecular Chemistry, 巻 16, 番号 19, 01.01.2018, p. 3584-3595.

研究成果: ジャーナルへの寄稿記事

Kato, SI, Jin, S, Kimura, T, Yoshikawa, N, Nara, D, Imamura, K, Shiota, Y, Yoshizawa, K, Katoono, R, Yamanobe, T, Uehara, H & Nakamura, Y 2018, 'Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: Synthesis, photophysical and electrochemical properties, and self-assembly behavior', Organic and Biomolecular Chemistry, 巻. 16, 番号 19, pp. 3584-3595. https://doi.org/10.1039/c8ob00471d
Kato, Shin Ichiro ; Jin, Satoshi ; Kimura, Terutaka ; Yoshikawa, Naoki ; Nara, Daiki ; Imamura, Kenji ; Shiota, Yoshihito ; Yoshizawa, Kazunari ; Katoono, Ryo ; Yamanobe, Takeshi ; Uehara, Hiroki ; Nakamura, Yosuke. / Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties : Synthesis, photophysical and electrochemical properties, and self-assembly behavior. :: Organic and Biomolecular Chemistry. 2018 ; 巻 16, 番号 19. pp. 3584-3595.
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abstract = "We report the synthesis, photophysical properties, redox characteristics, and self-assembly behavior of disk-shaped trithiazolyl-1,3,5-triazines that bear decyloxybenzene moieties. These compounds were synthesized by a Migita-Kosugi-Stille coupling reaction of 1,3,5-trichlorotriazine with three different tributyltin(thiazoles) as the key step. The structure-property relationships, namely the effects of the incorporation of thiazole units into the triazine unit, the conjugation connectivity between the thiazole and triazine units, and the insertion of ethynylene spacers between the thiazole and decyloxybenzene moieties on the properties of the trithiazolyl-1,3,5-triazines were comprehensively investigated. Binding of the triazine core at the 5-position of the thiazole moieties effectively extended the π-conjugation and afforded high fluorescence quantum yields. The ethynylene spacers substantially lowered the LUMO level relative to the HOMO level. The prepared trithiazolyl-1,3,5-triazines self-assembled in solution, and the introduction of thiazole units at the 5-position enhanced this behavior. Detailed thermodynamic studies on the self-association behavior were conducted, and the formation of self-assembled 1D clusters is disclosed.",
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AU - Kato, Shin Ichiro

AU - Jin, Satoshi

AU - Kimura, Terutaka

AU - Yoshikawa, Naoki

AU - Nara, Daiki

AU - Imamura, Kenji

AU - Shiota, Yoshihito

AU - Yoshizawa, Kazunari

AU - Katoono, Ryo

AU - Yamanobe, Takeshi

AU - Uehara, Hiroki

AU - Nakamura, Yosuke

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