基于四芳基咪唑的聚集诱导发光染料及其细胞成像应用

Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application

1,2,4,5-四苯基咪唑呈螺旋桨状高扭曲构象,具有发展成为聚集诱导发光分子的潜力.通过四组分“一锅煮”反应,高产率地合成了2个基于四芳基咪唑的荧光分子(TAI-m和TAI-q),通过核磁共振和高分辨质谱对其进行了结构表征,单晶结构证实了它们高度扭曲的分子构象.TAI-m和TAI-q都表现出优异的聚集诱导发光性质.对其自聚集纳米颗粒及F-127封装纳米颗粒的细胞染色及荧光成像性能做了比较研究.结果表明二者的染色行为明显不同,自聚集纳米颗粒染色的细胞显示清晰的细胞轮廓,但细胞内部染色效果较差,而F-127封装纳米颗粒能快速分布于整个细胞.

1,2,4,5-Tetraphenylimidazole takes a highly twisted propeller-like conformation,which results in its potential to be developed into aggregation-induced emission(AIE)-active molecules.Herein,two tetraarylimidazole-based aggregationinduced emission luminogens(TAI-m and TAI-q)were easily synthesized through a one-pot,four-component reaction in high yields.Their structures were fully characterized by nuclear magnetic resonance(NMR)and high-resolution mass spectra(HRMS).Furthermore,the crystal structures of them confirmed their highly twisted conformation.Both TAI-m and TAI-q exhibited good AIE properties.The self-aggregation nanoparticles and the pluronic F-127 encapsulated nanoparticles of them were prepared for comparative study of their cell imaging performance.The findings indicated that they showed the distinct staining behaviors.The cells stained with the self-aggregates showed clear cell outlines but fuzzy cell interiors.By comparison,the pluronic F-127 encapsulated nanoparticles can be distributed in the whole cell.