摘要
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.
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.
作者
黄凯航
尹理
姜青云
汪乾
石光
许炳佳
Huang Kaihang;Yin Li;Jiang Qingyun;Wang Qian;Shi Guang;Xu Bingjia;无(School of Chemistry,South China Normal University,Guangzhou 510006;Guangzhou Institutes of Biomedicine and Health,Chinese Academy of Sciences,Guangzhou 510530;Guangzhou Laboratory,Guangzhou 510320)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2024年第8期2479-2486,共8页
Chinese Journal of Organic Chemistry
基金
广东省自然科学基金(No.2023A1515010915)资助项目。
关键词
聚集诱导发光
热激活延迟荧光
脂滴
生物成像
aggregation-induced emission
thermally activated delayed fluorescence
lipid droplet
bioimaging
