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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3584-3595
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number19
DOIs
Publication statusPublished - Jan 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

Cite this

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.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 19, 01.01.2018, p. 3584-3595.

Research output: Contribution to journalArticle

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. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 19. pp. 3584-3595.
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