Synthesis and characterization of new linear π-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer

Md. Akhtaruzzaman, Masaaki Tomura, Md Badruz Zaman, Jun ichi Nishida, Yoshiro Yamashita

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Three novel 4,7-bis(n-pyridylethynyl)-2,1,3-benzothiadiazoles (n = 2, 3, and 4) were synthesized by using the Sonogashira cross-coupling reaction of 4,7-dibromo-2,1,3-benzothiadiazole with the corresponding ethynylpyridines in the presence of a Pd(II) catalyst. The viologen analogues were also prepared by methylation of pyridyl nitrogen atoms. X-ray structure analysis of these compounds revealed the linear molecular structures with unusual columnar crystal structures. Insertion of a benzothiadiazole moiety into the acetylene-pyridine skeleton brings about a large increase in electron affinity and the bispyridyl compounds obtained here show high fluorescence quantum yields.

Original languageEnglish
Pages (from-to)7813-7818
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number22
DOIs
Publication statusPublished - 1 Nov 2002
Externally publishedYes

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Viologens
Acetylene
Electron affinity
Molecules
Methylation
Quantum yield
Molecular structure
Nitrogen
Crystal structure
Fluorescence
X rays
Atoms
Catalysts
benzo-1,2,3-thiadiazole
ethynylpyridine
4,7-dibromo-2,1,3-benzothiadiazole
pyridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and characterization of new linear π-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer. / Akhtaruzzaman, Md.; Tomura, Masaaki; Zaman, Md Badruz; Nishida, Jun ichi; Yamashita, Yoshiro.

In: Journal of Organic Chemistry, Vol. 67, No. 22, 01.11.2002, p. 7813-7818.

Research output: Contribution to journalArticle

Akhtaruzzaman, Md. ; Tomura, Masaaki ; Zaman, Md Badruz ; Nishida, Jun ichi ; Yamashita, Yoshiro. / Synthesis and characterization of new linear π-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 22. pp. 7813-7818.
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