Synthesis and Characterization of New Linear π-Conjugated Molecules Containing Bis(ethynylpyridine) Units with a Benzothiadiazole Spacer
- 28 September 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (22) , 7813-7818
- https://doi.org/10.1021/jo0202334
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.Keywords
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