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具有C2v对称性二苯并噻吩衍生物的合成及光学特性
C2v symmetrical dibenzothiophene derivatives: Synthesis and photophysical properties
【摘要】 以二苯并噻吩为原料合成了中间体2,8-二溴二苯并噻吩和2,8-二甲酰基二苯并噻吩,并从这两种化合物出发,分别利用Heck反应和Wittig反应合成了具有C2v对称性的一系列二苯并噻吩衍生物。用核磁共振、红外、质谱等光谱手段表征了新化合物的结构,对这些化合物的光物理特性进行了评价。结果表明:2,8-二[2-(吡啶-4-基)乙烯基]二苯并噻吩(I)的紫外吸收峰随着溶剂极性的增加而出现蓝移现象,而其他化合物的紫外吸收峰随溶剂极性增加往长波方向移动;化合物I具有较低的荧光量子效率;用750~920 nm的飞秒激光激发时化合物I的溶液表现出明显的双光子吸收特性。
【Abstract】 Three C2v symmetrical π-conjugated dibenzothiophene derivatives have been synthesized from 2,8-dibromodibenzothiophene and 2,8-diformyldibenzothiophene by means of separate Wittig and Heck reactions.Their structures were verified by 1H-NMR,IR and MS spectra.Investigation of their photophysical properties showed:(1) an abnormal blue-shift in the UV-visible and fluorescence spectra of compound I with increasing solvent polarity,whilst red-shifts were observed in the UV-visible spectra of compounds Ⅱ and Ⅲ;(2) compound Ⅰ possesses low fluorescence quantum yield;(3) compound Ⅰ exhibits significant two photon absorption properties when excited with near IR laser light.
【Key words】 dibenzothiophene derivatives; C2v symmetry; photophysical properties;
- 【文献出处】 北京化工大学学报(自然科学版) ,Journal of Beijing University of Chemical Technology(Natural Science Edition) , 编辑部邮箱 ,2007年04期
- 【分类号】TQ251.2
- 【被引频次】4
- 【下载频次】272