Citation: Cai Liu, Lü Liu, Wang Mengying, Wu Yusheng, Huang Jinfeng, Zeng Xiangchao. Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1126-1137. doi: 10.6023/cjoc201709046 shu

Synthesis and Photophysical Properties of Multi-aryl Imidazoles Containing Nitrogen Heterocyclic Ring

College of Chemistry and Materials Science, Jinan University, Guangzhou 510632

Corresponding author: Zeng Xiangchao, xczeng@126.com
Received Date: 29 September 2017
Revised Date: 21 December 2017
Available Online: 18 May 2018
Fund Project: the National University Student Innovation Program of China 201610559039Project supported by the National University Student Innovation Program of China (No. 201610559039)

Figures(8)

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.
- imidazole,
- indole,
- carbazole,
- bioimaging,
- pH fluorescent probe
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