有机化学 ›› 1995, Vol. 15 ›› Issue (2): 161-169. 上一篇    下一篇

研究论文

苯并咪唑-噻碳菁染料的合成及性质

阎文鹏;彭必先;许慧君   

  1. 中国科学院感光化学研究所
  • 发布日期:1995-04-25

synthesis and properties of benzimidazolo-thiacarbocyanine dyes

YAN WENPENG;PENG BIXIAN;XU HUIJUN   

  • Published:1995-04-25

2-(β-苯胺基乙烯基)-5-R-3-(γ-磺酸丙基)苯并噻唑内铵盐同5,6-二氯-1-乙基-2-甲基-3-(γ-磺酸丙基)苯并咪唑内铵盐在乙酸酐-三乙胺存在下缩合生成苯并咪唑-噻碳菁染料, 合成并表征了七个不对称苯并咪唑-噻碳菁, 其中六个为新化合物. 测试了它们的紫外可见吸收光谱和荧光发射光谱, 结果表明 不对称染料的Brooker偏离值与取代基R的Hammettσ~m常数呈线性关系. 取代的苯并噻唑杂环碱性顺序: 4,5-苯并>5-CH~3>5-H>5-OCH~3>5-F>5-Cl>5-CF~3 .

关键词: 合成, 增感剂, 苯并咪唑-噻碳菁染料, 染料, 取代基效应

Seven unsymmetrical benzimidazdo-thiacarbocyanine dyes were synthesized by condensation of 2-(β-anioiovinyl)- 5-R-3-(γ-sylfopropyl) benzothiazolium betaine with 5,6- dichloro-1-ethyl-2-methyl-3-(γ-sulfopropyl) benzimidazolium betaine in Ac~2O-NEt~3 medium. A linear relationship between the Brooker deviation value of the unsymmetrical dyes and the Hammett σ~m-constant of the substituent R at the 5' position of benzene ring (benzothiazole heterocyclic nucleus) was observed. The sequence of the basicity of the nitrogen atom in the substituted benzothiazol heterocyclic ring was found to be 4,5-benzo>5-CH~3>5-H>5-OCH~3>5-F>5-Cl> 5-CF~3 .

Key words: SYNTHESIS, SENSITIZER, DYES, SUBSTITUENT EFFECT

中图分类号: