Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2479-2486.DOI: 10.6023/cjoc202403038 Previous Articles     Next Articles

ARTICLES

具有聚集诱导发光性质的高效热激活延迟荧光材料用于脂滴成像

黄凯航a, 尹理b, 姜青云a, 汪乾c,*(), 石光a, 许炳佳a,*()   

  1. a 华南师范大学化学学院 广州 510006
    b 中国科学院广州生物医药与健康研究院 广州 510530
    c 广州实验室 广州 510320
  • 收稿日期:2024-06-04 修回日期:2024-06-29 发布日期:2024-07-10
  • 基金资助:
    广东省自然科学基金(2023A1515010915)

Efficient Thermally Activated Delayed Fluorescence Materials with Aggregation-Induced Emission for Lipid Droplet Imaging

Kaihang Huanga, Li Yinb, Qingyun Jianga, Qian Wangc(), Guang Shia, Bingjia Xua()   

  1. a School of Chemistry, South China Normal University, Guangzhou 510006
    b Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530
    c Guangzhou Laboratory, Guangzhou 510320
  • Received:2024-06-04 Revised:2024-06-29 Published:2024-07-10
  • Contact: E-mail: bingjiaxu@m.scnu.edu.cn; wang_qian@gzlab.ac.cn
  • Supported by:
    Natural Science Foundation of Guangdong Province(2023A1515010915)

Thermally activated delayed fluorescence (TADF) materials with aggregation-induced emission (AIE) properties are promising for autofluorescence-free bioimaging. However, efficient AIE-TADF luminogens that can specifically target lipid droplets and enable high-quality fluorescence imaging are very limited. 3 new organic luminophores were successfully developed by introducing diphenylamine, 9,10-dihydro-9,9-diphenylanthracene, and 9,10-dihydro-9,9-dimethylanthracene, respectively, onto the phthalimide moiety, along with a lipid droplet-targeting group, morpholine. These compounds exhibited excellent AIE properties with fluorescence quantum yields up to 46.5% in the solid state. Moreover, 5-(diphenylamine)- 2-(2-morpholinoethyl)isoindoline-1,3-dione (1) and 5-(9,9-diphenylacridine-10(9H)-yl)-2-(2-morpholinoethyl) isoindoline-1,3- dione (2) only displayed prompt fluorescence, while 5-(9,9-dimethylacridine-10(9H)-yl)-2-(2-morpholinoethyl)isoindoline- 1,3-dione (3) demonstrated intense TADF. More importantly, 3 exhibited good biocompatibility and the ability to enter cells and specifically target lipid droplets, enabling high-brightness fluorescence imaging. The Pearson’s correlation coefficient between 3 and the commercially available lipid droplet dye Bodipy reached 0.87 in the imaging area. This work provides a new approach for the development of high-performance AIE-TADF molecules for bioimaging applications.

Key words: aggregation-induced emission, thermally activated delayed fluorescence, lipid droplet, bioimaging