4种近红外菁类染料的合成及其光学性能研究

Synthesis and Spectral Properties of Four Near-infrared Cyanine Dyes

通过分子设计分别以2-甲基苯并噻唑和1,1,2-三甲基-1H-苯并[e]吲哚为原料,首先合成了2种季铵盐,再分别同四乙氧基丙烷和3-(羟基亚甲基)-2-氯环己-1-烯甲醛缩合制备4种带有活性羟基的菁类染料。通过傅里叶红外光谱仪、核磁共振仪和高分辨率质谱对染料结构进行了表征。以DMF为溶剂,用紫外-可见光谱仪测定了4种染料的吸收光谱;采用电流为13.4 A的高压氙灯为灯源,考察染料的光稳定性。结果表明:4种菁类染料均在近红外区产生较强吸收;其中,共轭聚甲川链上含有六元环和吸电子基团的染料拥有较大的最大吸收波长。光稳定性的测试结果表明:以苯并吲哚含氮杂环为母体合成的染料,光稳定性更好,可以作为功能性染料使用。

In this paper,four cyanine dyes with active hydroxyl were synthesized using 1,1,3,3-tetraethoxypropane and 3-(hydroxylmethylene)-2-chcloro-cyclohex-1-enealdehyde which respectively condensed with two kinds quaternary ammonium salts prepared from 2-Methylbenzothiazole and 1,1,2-trimethyl-1 H-benz[e]indole.The dyes’structure was characterized by nuclear magnetic resonance spectra and high resolution mass spectrometry.The absorption spectra of the four dyes were determined by UV-vis with DMF as solvent.A high voltage xenon lamp with current of 13.4 A was used as the source of the light to study the light resistance of the dyes.The results showed that,the four cyanine dyes all have strong absorption in near infrared region,and the dyes containing six-membered ring and electron absorbing group on the conjugate polymethyl chain possess greaterλmax.The test of photostability shows that the dyes with benzoindole nitrogen heterocyclic ring as the main structure are more photostable and can be used as functional dyes.