TY - JOUR
T1 - Synthesis and characterization of new linear π-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer
AU - Akhtaruzzaman, Md
AU - Tomura, Masaaki
AU - Zaman, Md Badruz
AU - Nishida, Jun ichi
AU - Yamashita, Yoshiro
PY - 2002/11/1
Y1 - 2002/11/1
N2 - 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.
AB - 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.
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U2 - 10.1021/jo0202334
DO - 10.1021/jo0202334
M3 - Article
C2 - 12398508
AN - SCOPUS:0036827532
VL - 67
SP - 7813
EP - 7818
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -