有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1445-1449.DOI: 10.6023/cjoc1201091 上一篇    下一篇

研究论文

新型不对称苯并噻唑三次甲基菁染料的合成及光稳定性研究

陈秀英, 郭琳, 郑昌戈, 高海燕, 王海军, 张丹   

  1. 江南大学食品胶体与生物技术教育部重点实验室 江南大学化学与材料工程学院 无锡 214122
  • 收稿日期:2012-01-09 修回日期:2012-04-23 出版日期:2012-08-25 发布日期:2012-05-11
  • 通讯作者: 陈秀英 E-mail:chenxiuying1975@163.com
  • 基金资助:

    国家自然科学基金(No.20706026)、中央高校基本科研业务费专项资金(Nos. JUSRP211A12, JUSRP21110)资助项目.

Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes

Chen Xiuying, Guo Lin, Zheng Changge, Gao Haiyan, Wang Haijun, Zhang Dan   

  1. Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122
  • Received:2012-01-09 Revised:2012-04-23 Online:2012-08-25 Published:2012-05-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20706026) and the Fundamental Research Funds for the Central Universities (Nos. JUSRP211A12, JUSRP21110).

合成了系列杂环氮原子具有不同取代基的不对称苯并噻唑三次甲基菁染料, 染料结构经过质谱、1H NMR表征. 测试了染料在乙醇中的吸收和荧光发射光谱, 染料的最大吸收值和荧光发射值分别在628~631和662~666 nm之间. 染料在溶剂中几乎无荧光, 可以极大的降低染料自身的荧光背景干扰. 染料的光降解实验表明: 喹啉环上辛烷基取代和噻唑环上苄基取代时, 染料的光稳定性最强. 染料8a8d的光降解速率常数分别为6.38×10-4, 12.5×10-4, 2.68×10-4和6.30×10-4 mol·min-1. 循环伏安实验法测试了染料的氧化电位.

关键词: 苯并噻唑菁染料, 光降解, 循环伏安曲线, 荧光, 氧化电位, 光稳定性

Novel asymmetric trimethine benzothiazole cyanine dyes with different N-substituents were synthesized and characterized by MS and 1H NMR techniques. The maximums of absorption and emission spectra of the dyes in ethanol were in the range of 628~631 and 662~666 nm, respectively. The dyes were almost non-fluorescent in solvents, which can reduce the background interference greatly. The photodegradation experiment showed that the octyl group on quinoline ring and benzyl group on benzothiazole ring improved the photostabilites of the dyes obviously. The rate constants of photoreaction of the dyes 8a8d were 6.38×10-4, 12.5×10-4, 2.68×10-4 and 6.30×10-4 mol·min-1, respectively. Oxidation potentials were determined by cyclic voltammetry.

Key words: benzothiazole cyanine dye, photodegradation, cyclic voltammetry curves, fluorescence, oxidizing potential, photostability