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 journalArticlepeer-review

38 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 - 2002 Nov 1

ASJC Scopus subject areas

  • Organic Chemistry

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