一种新型菲并咪唑类衍生物的合成及聚集诱导发光性质和细胞成像

Synthesis and Aggregation-induced Emission(AIE) Properties of A New Phenanthroimidazole Derivative and Its Cell Imaging

以9,10-菲醌为原料,通过Debus-Radziszewski反应合成新化合物2-[1-(4-碘苯基)-1 H -菲并咪唑基]苯酚( 2 );再通过Heck反应引入4-乙烯基吡啶合成了一种新的菲并咪唑衍生物2-[1-(4-乙烯基吡啶基苯基)-1 H -菲并咪唑基]苯酚( 3 ),其结构经 1 H NMR、 13 C NMR、 HR-MS (ESI)和元素分析表征。通过紫外-可见吸收光谱和荧光发射光谱研究了其光学性质。结果表明: 3 在水中具有明显的聚集诱导发光性质,在含水量为90%的 DMF/H 2O 溶剂中,荧光强度增强了6倍。 3 在DMSO-H 2 O混合溶剂中具有类似的AIE现象,含水量为70%时荧光强度最大。此外, 3 的细胞毒性小,生物成像实验表明: 3 可有效应用于细胞成像。

Using 9,10-phenanthraquinone as the raw material, a new compound 2-(1-(4-iodophenyl)-1 H -phenamimidazolyl)phenol( 2 ) was synthesized by Debus-Radziszewski reaction. A new phenanthroimidazole derivative, 2-(1-(4-vinylpyridyl)phenyl)-1 H -phenamimidazolyl)phenol( 3 ),was synthesized by Heck reaction of 2 with 4-vinylpyridine. The structures were characterized by 1 H NMR, 13 C NMR, HR-MS(ESI) and elemental analysis. The optical properties of 3 were preliminarily investigated by UV-Vis and fluorescence spectra. The results showed that compound 3 possessed evident aggregation-induced emission properties in water. When the contents of water in DMF/H 2 O was 90%, the fluorescence intensity increased to be 6-fold. A similar AIE phenomenon was found in DMSO/H 2 O mixed solvents, and the fluorescence intensity of 3 reached its maximum when the content of water was 70%. In addition, the cytotoxicity of 3 was low, and the cell imaging experiment revealed that compound 3 can be used for bio-imaging in living cell.