Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2454-2461.DOI: 10.6023/cjoc202212004 Previous Articles     Next Articles



赵洋, 陈盼盼, 韩立志*(), 王恩举*()   

  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 热带药用植物化学海南省重点实验室 海口 571158
  • 收稿日期:2022-12-05 修回日期:2023-03-04 发布日期:2023-03-30
  • 通讯作者: 韩立志, 王恩举
  • 基金资助:

Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives

Yang Zhao, Panpan Chen, Lizhi Han(), Enju Wang()   

  1. 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
  • Received:2022-12-05 Revised:2023-03-04 Published:2023-03-30
  • Contact: Lizhi Han, Enju Wang
  • Supported by:
    Natural Science Foundation of Hainan Province(222MS059)

Aggregation-induced emission (AIE)-active materials have great advantages in the biomedical field and open up a whole new world of opportunity for bioimaging. Herein, two butylidene-bridged bisimidazole derivatives and two butyl-sub- stituted monoimidazole derivatives were easily synthesized from dibromobutane/bromobutane and 2,4,5-triphenyl-1H-imida- zole derivatives. All the obtained imidazole derivatives showed excellent AIE properties, and the derivatives containing methoxy groups exhibited red-shifted emission. The research on AIE mechanism indicated that the restriction of twisted intramolecular charge transfer (TICT) mechanism was responsible for the AIE behaviors of these imidazole derivatives. Therefore, the strong electron-withdrawing nitro group is crucial for their AIE property. In addition, the steric effect of the substituent group at 1-position of imidazole ring is also indispensable for AIE, because it results in the twisted conformation and thus hampers the intermolecular π-π stacking interactions. Ultimately, the cell staining and bioimaging behaviour of butyl-substituted monoimidazole derivatives were investigated. Both of them displayed an excellent bioimaging performance in blue, green and red channels, but the different staining regions in cells were observed in different channels.

Key words: aggregation-induced emission (AIE), triphenylimidazole, twisted intramolecular charge transfer (TICT), twisted conformation