一种新型水溶性聚集诱导发光探针的合成  

Synthesis of A Novel Water-soluble Aggregation-induced Emission Fluorescent Probe

作　　者：谢样梓 李莹[2] 罗媛 蔡林涛[2] 焦哲 张鹏飞[2] XIE Yangzi;LI Ying;LUO Yuan;CAI Lintao;JIAO Zhe;ZHANG Pengfei(School of Environment And Civil Engineering,Dongguan University of Technology,Dongguan 523106,China;Institute of Biomedicine and Biotechnology,Shenzhen Institute of Advanced Technology Chinese Academy of Sciences,Shenzhen 518055,China)

机构地区：[1]东莞理工学院生态环境与建筑工程学院,广东东莞523106 [2]中国科学院深圳先进技术研究院生物医药与技术研究所,广东深圳518055

出　　处：《合成化学》2023年第7期533-538,共6页Chinese Journal of Synthetic Chemistry

基　　金：中国科学院院级重大科研仪器研制项目(ZDKYYQ20220008)。

摘　　要：传统有机染料在稀溶液中表现出强烈的荧光现象,而在聚集态的情况下,因受到聚集诱导淬灭效应(ACQ)的影响,荧光强度会大幅度降低,致使光量子产率低,很大程度上限制了有机染料的应用。基于在生物学的研究中,通常以水相的方式进行,然而有机染料水溶性差且生物相容性差。因此,以简单的方法合成水溶性的AIE染料在研究中具有很大的优势。本文以4,4′-[(4-溴苯基)亚甲基]双(N,N-二甲基苯胺)和5-甲酰基呋喃-2-硼酸作为底物经过Suzuki偶联反应得到水溶性聚集诱导发光(AIE)材料MG-A。通过^(1)H NMR,^(13)C NMR,HR-MS(ESI)等分析表征,确定了产物的结构。通过光物理表征和活细胞共聚焦成像实验证明了本文中合成的分子MG-A具有良好的水溶性以及聚集诱导发光特性,活细胞共定位成像实验结果显示MG-A具有很好的线粒体靶向性。Traditional organic dyes show strong fluorescence in dilute solution, but in the case of aggregation, due to the influence of aggregation caused quenching (ACQ), the fluorescence intensity will be greatly reduced, resulting in low quantum yield, which greatly limits the application of organic dyes. In biological research, it is usually carried out in an aqueous phase, but organic dyes have poor water solubility and biocompatibility. Therefore, synthesizing water-soluble AIE dyes using a simple method has great advantages in research. In this paper, 4,4′- [(4-bromophenyl) methylene] bis( N, N -dimethylaniline) and 5-formaldehyde furan-2-boric acid were used as substrates to undergo Suzuki coupling reaction under the protection of argon. After purification, compound 1 was obtained. After purification, water-soluble aggregation-induced luminescence(AIE) material MG-A was obtained. MG-A were characterized by ^(1)H NMR, ^(13)C NMR and HR-MS analysis. The photophysical characterization and living cell confocal imaging experiments prove that the molecule MG-A synthesized in this paper has good water solubility and aggregation-induced luminescence characteristics. The living cell colocalization imaging experiment showed that MG-A was successfully targeting mitochondrial.

关 键 词：水溶性 染料 聚集诱导发光 有机合成 线粒体 活细胞成像 

分 类 号：O623.732[理学—有机化学] O621.3[理学—化学]