含氮杂环多芳基咪唑衍生物的合成及其光物理性能

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

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p H值敏感且结构独特的两个化合物作为p H荧光探针,检测在其作用下MCF-7细胞在不同p H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p H变化的p H荧光探针.

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 p H-sensitive were selected as p H fluorescent probes.Furthermore,the fluorescence imaging of MCF-7 cells in different p H environments in the presence of the probe 2-（9-benzyl-9 H-carbazol-3-yl）-1 H-4,5-diphenylimidazole（2 d） or 2-（9-benzyl-9 H-carbazol-3-yl）-1 H-phenanthro[9,10-d]imidazole（4） was detected,and the results revealed that the two probes show promising potential to be used in detecting p H changes in living cells as p H fluorescent probes.