新型三苯胺-苯并噻唑衍生物的多重荧光和过氧化氢响应特性
Multiple fluorescence and hydrogen peroxide-responsive properties of novel triphenylamine-benzothiazole derivatives.
作者信息
Tang Jiyu, Zhang Kaiming, Ni Tong, Xu Bin, Hou Binjie, Liu Xiaoqiang, Jiang Weidong
机构信息
School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, P. R. China.
Key Laboratory of Green Catalysis of Sichuan Institute of High Education, Zigong, Sichuan 643000, P. R. China.
出版信息
Anal Methods. 2023 Aug 17;15(32):4021-4031. doi: 10.1039/d3ay01038d.
A novel fluorescent dye molecule - triphenylamine (TPA)-benzothiazole (BZT) - based on excited state intramolecular proton transfer (ESIPT) was prepared by the Suzuki coupling reaction. The photophysical property assay indicates that BZT-TPA appeared in distinguishable colors in mixed solvents with different water contents. Moreover, BZT-TPA exhibited observable AIE behavior. On this basis, a fluorescent probe BZT-TPA-BO was synthesized for detecting HO. This probe molecule was found to have excellent selectivity, rapid response, and good linear relationship ( = 0.989) for detecting HO in aqueous medium. Through DFT calculation, fluorescence spectrum, nuclear magnetic titration and HR-MS, the mechanism of recognition of HO by the probe BZT-TPA-BO is proposed. In addition, the probe BZT-TPA-BO to some extent exhibited better performance for detecting exogenous HO in HeLa cells.
通过铃木偶联反应制备了一种基于激发态分子内质子转移（ESIPT）的新型荧光染料分子——三苯胺（TPA）-苯并噻唑（BZT）。光物理性质测定表明，BZT-TPA在不同水含量的混合溶剂中呈现出可区分的颜色。此外，BZT-TPA表现出明显的聚集诱导发光（AIE）行为。在此基础上，合成了一种用于检测HO的荧光探针BZT-TPA-BO。发现该探针分子在水性介质中检测HO具有优异的选择性、快速响应和良好的线性关系（=0.989）。通过密度泛函理论（DFT）计算、荧光光谱、核磁共振滴定和高分辨质谱（HR-MS），提出了探针BZT-TPA-BO识别HO的机制。此外，探针BZT-TPA-BO在一定程度上表现出在HeLa细胞中检测外源性HO的更好性能。
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