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

作　　者：赵洋 陈盼盼 李高楠[1,2] 钮智刚 王恩举[1] Zhao Yang;Chen Panpan;Li Gaonan;Niu Zhigang;Wang Enju(Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province,Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education,College of Chemistry&Chemical Engineering,Hainan Normal University,Haikou 571158;Key Laboratory of Emergency and Trauma,Ministry of Education,College of Emergency and Trauma,Hainan Medical University,Haikou 571199)

机构地区：[1]海南师范大学化学与化工学院热带药用资源化学教育部重点实验室海南省热带药用植物化学重点实验室,海口571158 [2]海南医学院急救与创伤学院急救与创伤研究教育部重点实验室,海口571199

出　　处：《有机化学》2023年第6期2156-2162,共7页Chinese Journal of Organic Chemistry

基　　金：急救与创伤研究教育部重点实验室(海南医学院)开放课题基金(No.KLET-202011);海南省自然科学基金(No.222MS059)资助项目。

摘　　要：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.

关 键 词：聚集诱导发射 四芳基咪唑 自聚集纳米颗粒 封装的纳米颗粒 细胞成像 

分 类 号：Q2-33[生物学—细胞生物学] TQ617.8[化学工程—精细化工]