基于四芳基咪唑的聚集诱导发光染料及其细胞成像应用
收稿日期: 2022-10-02
修回日期: 2022-12-15
网络出版日期: 2023-01-05
基金资助
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(KLET-202011); 海南省自然科学基金(222MS059)
Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application
Received date: 2022-10-02
Revised date: 2022-12-15
Online published: 2023-01-05
Supported by
Open Research Fund Program of Key Laboratory of Emergency and Trauma(Hainan Medical University),Ministry of Education(KLET-202011); Hainan Provincial Natural Science Foundation(222MS059)
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.
赵洋 , 陈盼盼 , 李高楠 , 钮智刚 , 王恩举 . 基于四芳基咪唑的聚集诱导发光染料及其细胞成像应用[J]. 有机化学, 2023 , 43(6) : 2156 -2162 . DOI: 10.6023/cjoc202210002
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 aggregation- induced 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.
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