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
收稿日期: 2024-06-04
修回日期: 2024-06-29
网络出版日期: 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
Received date: 2024-06-04
Revised date: 2024-06-29
Online published: 2024-07-10
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.
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, 2024 , 44(8) : 2479 -2486 . DOI: 10.6023/cjoc202403038
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.
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