含氮杂环多芳基咪唑衍生物的合成及其光物理性能
收稿日期: 2017-09-29
修回日期: 2017-12-21
网络出版日期: 2018-01-18
基金资助
国家大学生创新创业训练计划（No.201610559039）资助项目.
Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring
Received date: 2017-09-29
Revised date: 2017-12-21
Online published: 2018-01-18
Supported by
Project supported by the National University Student Innovation Program of China (No. 201610559039).
以冰醋酸为溶剂和催化剂，苯偶酰/9，10-菲醌、3-吲哚甲醛/3-咔唑甲醛及醋酸铵经“一锅”反应高效合成了系列含吲哚或咔唑结构单元的多取代咪唑衍生物.考察了反应物配比、溶剂的选择和用量及温度等因素对反应的影响，研究了所合成化合物的光物理性能；筛选出对pH值敏感且结构独特的两个化合物作为pH荧光探针，检测在其作用下MCF-7细胞在不同pH值环境中的荧光成像，结果表明探针2-（9-苄基-9H-咔唑-3-基）-4，5-二苯基-1H-咪唑（2d）和2-（9-苄基-9H-咔唑-3-基）-1H-菲并[9，10-d]咪唑（4）都可用作检测活细胞内pH变化的pH荧光探针.
蔡柳, 吕柳, 王梦颖, 吴禹胜, 黃锦锋, 曾向潮 . 含氮杂环多芳基咪唑衍生物的合成及其光物理性能[J]. 有机化学, 2018 , 38(5) : 1126 -1137 . DOI: 10.6023/cjoc201709046
A series of novel imidazole derivatives containing indole or carbazole unit were efficiently synthesized via one-pot reaction of benzil/9, 10-phenanthraquinone, indole-3-carbaldehyde/carbazole-3-carbaldehyde and ammonium acetate utilizing glacial acetic acid as solvent and catalyst. The effects of selection and amount of solvents, molar ratio of the reagents, and temperature on the reactions have been surveyed. The photophysical properties of the synthesized products were also investigated, and two compounds possessing structural characteristics and pH-sensitive were selected as pH fluorescent probes. Furthermore, the fluorescence imaging of MCF-7 cells in different pH environments in the presence of the probe 2-(9-benzyl- 9H-carbazol-3-yl)-1H-4, 5-diphenylimidazole (2d) or 2-(9-benzyl-9H-carbazol-3-yl)-1H-phenanthro [9, 10-d]imidazole (4) was detected, and the results revealed that the two probes show promising potential to be used in detecting pH changes in living cells as pH fluorescent probes.
Key words： imidazole; indole; carbazole; bioimaging; pH fluorescent probe
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