Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2156-2162.DOI: 10.6023/cjoc202210002 Previous Articles     Next Articles


赵洋a, 陈盼盼a, 李高楠a,b, 钮智刚a,b, 王恩举a,*()   

  1. a 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
    b 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
  • 收稿日期:2022-10-02 修回日期:2022-12-15 发布日期: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

Yang Zhaoa, Panpan Chena, Gaonan Lia,b, Zhigang Niua,b, Enju Wanga,*()   

  1. a 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
    b Key Laboratory of Emergency and Trauma, Ministry of Education, College of Emergency and Trauma, Hainan Medical University, Haikou 571199
  • Received:2022-10-02 Revised:2022-12-15 Published:2023-01-05
  • Contact: E-mail:
  • 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-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.

Key words: aggregation-induced emission, tetraarylimidazole, self-aggregation nanoparticles, encapsulated nanoparticles, cell imaging