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Synthesis, Mesogenic and Spectroscopic Properties of 2,5-Disubstituted Thiophene Derivatives
作者姓名:韩杰  王彦美  王晓光
作者单位:Department of Chemistry, Nankai University, Tianjin 300071, China
基金项目:Project supported by the National Natural Science Foundation of China (No. 20402009) and the Personnel Unit of Nankai University.
摘    要:Two series of 2,5-disubstituted thiophene derivatives (series 1: 2,5-bis(p-alkoxyphenylethynyl)thiophene and series 2: 2,5-bisp-(p-alkoxyphenylethynyl)(phenylethynyl)]thiophene) were synthesized and characterized by ^1H NMR, ^13C NMR, HRMS and elemental analysis. The relationship between the structure and the mesogenic and spectroscopic properties has been discussed. The results show that compounds 1a-1f all exhibited an enantiotropic nematic mesophase, which was confirmed by the polarized optical microscopy (POM), differential scanning calorimeter (DSC) and variable temperature powder X-ray diffraction (PXRD). In contrast, the extended conjugated analogues 2a-2b had no liquid crystal properties. As for the spectroscopic properties, incorporating more phenylethynyl units results in red-shifted absorption and emission spectra, greatly enhanced quantum efficiency.

关 键 词:噻吩  液晶性质  分光光谱性质  合成  结构表征
收稿时间:2006-03-27
修稿时间:2006-03-272006-06-01

Synthesis, Mesogenic and Spectroscopic Properties of 2,5-Disubstituted Thiophene Derivatives
HAN, Jie, WANG, Yan-Mei, WANG, Xiao-Guang.Synthesis, Mesogenic and Spectroscopic Properties of 2,5-Disubstituted Thiophene Derivatives[J].Chinese Journal of Chemistry,2006,24(11):1594-1598.
Authors:HAN  Jie  WANG  Yan-Mei  WANG  Xiao-Guang
Institution:Department of Chemistry, Nankai University, Tianjin 300071, China
Abstract:Two series of 2,5‐disubstituted thiophene derivatives (series 1 : 2,5‐bis(p‐alkoxyphenylethynyl)thiophene and series 2 : 2,5‐bisp‐(p‐alkoxyphenylethynyl)(phenylethynyl)]thiophene) were synthesized and characterized by 1H NMR, 13C NMR, HRMS and elemental analysis. The relationship between the structure and the mesogenic and spectroscopic properties has been discussed. The results show that compounds 1a – 1f all exhibited an enantiotropic nematic mesophase, which was confirmed by the polarized optical microscopy (POM), differential scanningcalorimeter (DSC) and variable temperature powder X‐ray diffraction (PXRD). In contrast, the extended conjugated analogues 2a – 2b had no liquid crystal properties. As for the spectroscopic properties, incorporating more phenylethynyl units results in red‐shifted absorption and emission spectra, greatly enhanced quantum efficiency.
Keywords:thiophene  liquid crystal property  spectroscopic property
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