Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (06): 843-849. Previous Articles     Next Articles

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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

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