Iterative synthesis and characterization of cross-conjugated iso-polydiacetylenes

被引：50

作者：

Zhao, YM ^{[1
]}

Campbell, K ^{[1
]}

Tykwinski, RR ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 02期

关键词：

D O I：

10.1021/jo015810n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iterative synthesis of cross-conjugated iso-polydiacetylenes (iso-PDAs) is reported based on three fundamental building blocks: vinyl triflates 8, 9, and 25. An efficient sequence of palladium-catalyzed cross-coupling reactions of vinyl triflates and terminal alkynes has been employed to extend the chain length of these oligomers. The longest member of the series, nonamer 19, spans 3.4 nm from Si to Si atom. The stability and solubility of the conjugated oligomers have been evaluated as a function of pendant substitution. Assessment of solid-state structural properties was achieved via X-ray crystallographic analyses of monomer 12 and trimer 14. The electronic characteristics of the monodisperse oligomers have been fully analyzed by UV-vis spectroscopy in solution and as thin films, and these studies suggest that pi-electron communication is present along the enyne framework, but quickly reaches saturation by the stage of nonamer 19.

引用

页码：336 / 344

页数：9

共 67 条

[31] Rapid solid-phase synthesis of oligo(1,4-phenylene ethynylene)s by a divergent convergent tripling strategy [J].