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

doi:10.6023/cjoc202403038

摘要/Abstract

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. 为此, 本工作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, 成功获得了新型的有机发光分子1、2和3. 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, 1和2只能产生荧光, 而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. In this work, new organic luminophores, namely 1, 2, and 3, 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, pyridine. These compounds exhibited excellent AIE properties, with fluorescence quantum yields up to 46.5% in the solid state. Moreover, while 1 and 2 only displayed prompt fluorescence, 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

引用此文

黄凯航, 尹理, 姜青云, 汪乾, 石光, 许炳佳. 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[J]. 有机化学, doi: 10.6023/cjoc202403038.

Kaihang Huang, Li Yin, Qingyun Jiang, Qian Wang, Guang Shi, Bingjia Xu. Efficient Thermally Activated Delayed Fluorescence Materials with Aggregation-Induced Emission for Lipid Droplet Imaging[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202403038.

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