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4H-吡咯并[1,2-a]苯并咪唑的合成及其荧光性质
Synthesis and Fluorescence Properties of 4H-Pyrrolo[1,2-a]Benzimidazoles
【摘要】 合成了一系列4H吡咯并[1,2-a]苯并咪唑类化合物,测量了它们乙醇溶液的紫外/可见吸收光谱和荧光光谱并计算出各自的荧光量子效率.对化合物(5a~5m)的吸收光谱和荧光光谱进行了比较分析,发现化合物(5a~5m)在200~400nm范围内,都有3或3个以上较强的π→π电子跃迁紫外吸收峰,化合物(5b,5c,5i)在360~440nm区域有较强的荧光发射峰和较高的荧光量子效率;研究了化合物(5a~5m)分子中不同取代基对荧光光谱和荧光量子效率的影响,认为4H吡咯并[1,2-a]苯并咪唑环上的-CN和-CO2Et具有较好的荧光助色作用,而-COPh、-COMe则对分子的荧光具有猝灭作用,发现荧光量子效率较好的化合物(5b,5c,5i)可进一步修饰成为探针化合物或用于与DNA等生物大分子相互作用机理的研究.
【Abstract】 A series of 4H-pyrrolo[1,2-a]benzimidazoles are synthesized, the UV and fluorescence spectra of 4H-yrrolo[1,2-a]benzimidazoles (5a~5m) are measured, and their fluorescence quantum yields are determined. The UV and fluorescence spectra of the heading compounds are analysised and compared, it is found that compounds (5b,5c,5i) have strong fluorescence in the region 360~440nm with high fluorescence quantum yields and the fluorescence quantum yields increase if cyano group or ester group is introduced into the 4H-pyrrolo[1,2-a]benzimidazole ring, and the presence of acetyl or benzoyl as substituent in 4H-pyrrolo[1,2-a]benzimidazole results in fluorescence quenching. The 4H-yrrolo[1,2-a]benzimidazole (5b,5c,5i) which have high fluorescence quantum yields are shown to be useful fluorophores used in the construction of probe compounds or used to study the interaction mechanism of pyrrolobenzimidazoles with DNA.
【Key words】 4H-pyrrolo[1; 2-a]benzimidazole; fluorescence spectrum; fluorescence quantum yield;
- 【文献出处】 南京师大学报(自然科学版) ,Journal of Nanjing Normal University(Natural Science Edition) , 编辑部邮箱 ,2005年02期
- 【分类号】O626.13
- 【被引频次】3
- 【下载频次】308