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

被引:39
作者
Akhtaruzzaman, M
Tomura, M
Zaman, MB
Nishida, J
Yamashita, Y [1 ]
机构
[1] Tokyo Inst Technol, Dept Elect Chem, Interdisciplinary Grad Sch & Engn, Midori Ku, Yokohama, Kanagawa 2268502, Japan
[2] Grad Univ Adv Studies, Dept Struct Mol Sci, Okazaki, Aichi 4448585, Japan
[3] Inst Mol Sci, Okazaki, Aichi 4448585, Japan
[4] Natl Res Council Canada, Steacie Inst Mol Sci, Ottawa, ON K1A 0R6, Canada
关键词
D O I
10.1021/jo0202334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:7813 / 7818
页数:6
相关论文
共 54 条