Synthesis and Characterization of Novel Dipyridylbenzothiadiazole and Bisbenzothiadiazole Derivatives

Md. Akhtaruzzaman, Masaaki Tomura, Jun Ichi Nishida, Yoshiro Yamashita

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Novel dipyridyl compounds containing a mono- and bisbenzothiadiazole unit were synthesized using the Stille coupling reaction. Their pyridinium salts, viologen analogues, were also prepared by the N-alkylation. The X-ray crystallographic analysis of the compounds containing a benzothiadiazole ring revealed nonplanar molecular structures and unique crystal structures depending on the nitrogen positions. The dipyridyl compounds are efficient fluorophores with high electron affinity. The derivative afforded complexes with chloranilic acid and cyanuric acid composed of hydrogen bonding networks. The methyl viologen analogues showed two-stage one-electron reduction waves.

Original languageEnglish
Pages (from-to)2953-2958
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number9
DOIs
Publication statusPublished - 30 Apr 2004
Externally publishedYes

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Viologens
Electron affinity
Paraquat
Fluorophores
Alkylation
Molecular structure
Hydrogen bonds
Nitrogen
Salts
Crystal structure
Derivatives
X rays
Electrons
benzo-1,2,3-thiadiazole
chloranilic acid
cyanuric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and Characterization of Novel Dipyridylbenzothiadiazole and Bisbenzothiadiazole Derivatives. / Akhtaruzzaman, Md.; Tomura, Masaaki; Nishida, Jun Ichi; Yamashita, Yoshiro.

In: Journal of Organic Chemistry, Vol. 69, No. 9, 30.04.2004, p. 2953-2958.

Research output: Contribution to journalArticle

Akhtaruzzaman, Md. ; Tomura, Masaaki ; Nishida, Jun Ichi ; Yamashita, Yoshiro. / Synthesis and Characterization of Novel Dipyridylbenzothiadiazole and Bisbenzothiadiazole Derivatives. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 9. pp. 2953-2958.
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