有机化学 ›› 2011, Vol. 31 ›› Issue (06): 843-849. 上一篇    下一篇

研究论文

N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物的合成与荧光性质研究

范梅,谢志雄,徐之涵,平冰,赵圣印*   

  1. (东华大学化学化工与生物工程学院 上海 201620)
  • 收稿日期:2010-08-13 修回日期:2010-12-22 发布日期:2011-02-14
  • 通讯作者: 赵圣印 E-mail:syzhao8@dhu.edu.cn

Synthesis and Fluorescence Properties of N-Benzamidobisindolylmaleimide Derivatives

FAN Mei, XIE Zhi-Xiong, XU Zhi-Han, PING Bing, ZHAO Sheng-Yin   

  1. (College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620)
  • Received:2010-08-13 Revised:2010-12-22 Published:2011-02-14

以琥珀酰亚胺为原料, 经溴代、吲哚加成、与水合肼反应、酰基化和烷基化等反应, 设计合成了6a6c7a7b共5个新型N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物, 其结构经IR, 1H NMR和HRMS等进行了表征, 并研究了该类化合物的紫外、荧光性能和热性质. 研究表明, N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物的紫外吸收光谱在360~400和450~500 nm显示两个主要吸收峰, 将N原子甲基化和苄基化后, 紫外吸收峰波长发生红移. 以化合物紫外最大吸收波长为激发波长, 目标化合物的荧光发射光谱在560~620 nm有最大发射峰, 7a有最大的荧光量子产率, 7a在不同溶剂中随溶剂极性的增大, 量子产率没有明显的变化规律, 讨论了化合物的结构对荧光性能的影响. 热学性质研究表明, 化合物7a7b的玻璃化转变温度(Tg)分别为116和80 ℃, 目标化合物的分解温度接近400 ℃.

关键词: 双吲哚马来酰亚胺, 紫外, 荧光性能, 热稳定性

Five novel N-benzamidobisindolylmaleimide derivatives 6a6c and 7a7b were designed and synthesized from succiminide by bromination, indole addition, hydrazine cyclization, acylation, alkylation and so on. Their structures were confirmed by IR, 1H NMR and HRMS techniques. Their ultraviolet and fluorescence properties have been studied. The results suggested that the target compounds showed two maximum absorption peaks at 360~400 and 450~500 nm in UV spectrum. The maximum emision wavelength was around 560~620 nm in fluoresecnce spectrum. The effect of structure of the compounds on fluorescence properties was also discussed. Using rhodamine B as a reference, the fluorescence quantum yields for all compounds were detected. The compound 7a has the strongest fluorescence quantum yield. The results showed that the polarity of the solvents has a little effect on the fluorescence quantum yields. Thermal behavior of the compounds 7a and 7b have been investigated by DSC (different scanning calorimetric) and TGA (thermogravimetric analysis). Glass-transition temperature (Tg) of 7a and 7b appeared at 80 and 116 ℃, respectively. The high thermal stabilities for the target compounds were confirmed by TGA experiment. No sign of decomposition appeared upon heating below 400 ℃.

Key words: bisindolylmaleimide, ultraviolet analysis, fluorescence property, thermal stability