有机化学 ›› 2024, Vol. 44 ›› Issue (8): 2479-2486.DOI: 10.6023/cjoc202403038 上一篇    下一篇

研究论文

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)

具有聚集诱导发光(AIE)性质的热激活延迟荧光(TADF)材料可作为染料标记物用于无自体荧光的生物成像. 然而, 可特异性靶向至脂滴并进行高质量荧光成像的高效AIE-TADF染料目前极少有报道. 通过在邻苯二甲酰亚胺单元上分别引入二苯胺、9,10-二氢-9,9-二苯基吖啶、9,10-二氢-9,9-二甲基吖啶等结构不同的电子给体以及连接脂滴靶向基团吗啉, 成功获得了三个新型的有机发光分子. 研究发现, 所合成的化合物均表现出优异的AIE性能, 其在固态下的荧光量子产率可达46.5%. 同时, 5-(二苯胺基)-2-(2-吗啉基乙基)异吲哚啉-1,3-二酮(1)和5-(9,9-二苯基吖啶-10(9H)-基)-2-(2-吗啉基乙基)异吲哚啉-1,3-二酮(2)只能产生荧光, 而5-(9,9-二甲基吖啶-10(9H)-基)-2-(2-吗啉基乙基)异吲哚啉- 1,3-二酮(3)则可以发射高亮度的TADF. 更重要的是, 3不仅具有良好的生物相容性, 而且可以进入细胞并特异性靶向至脂滴, 从而实现高亮度的荧光成像. 其与商用脂滴染色剂Bodipy的成像区域的Pearson相关系数高达0.87. 该工作为用于生物成像的高性能AIE-TADF分子的开发提供了新的思路.

关键词: 聚集诱导发光, 热激活延迟荧光, 脂滴, 生物成像

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