Multiple Fluorescent Properties and Response to Hydrogen Peroxide of Developed Benzothiazole Derivatives

Novel fluorescent dye molecules-triphenylamine (TPA)-benzothiazole (BZT) based on excited state intramolecular proton transfer (ESIPT) were prepared by Suzuki coupling reaction. Photophysical property assay indicates that BZT-TPA appeared distinguishable colors in mixed solvents with different water content. Moreover, BZT-TPA exhibited observable AIE behavior. On this basis, a developed fluorescent probe BZT-TPA-BO was synthesized for detecting H2O2. This probe molecule was found to has excellent selectivity, rapid response, good linear relationship (R2 = 0.989) for detecting H2O2 in aqueous medium. Through DFT calculation, fluorescence spectrum, nuclear magnetic titration and HR-MS, the recognition mechanism of the probe BZT-TPA-BO to H2O2 was proposed. In addition, the probe BZT-TPA-BO to some extent possessed better performance for detecting exogenous H2O2 in HeLa cells.

Keywords: benzothiazole-based fluorescent dye, ESIPT emission, AIE effect, H2O2 response, cell imaging

Suggested Citation: Suggested Citation

Tang, Jiyu and Zhang, Kaiming and Ni, Tong and Xu, Bin and Hou, Binjie and Liu, Xiaoqiang and Jiang, Weidong, Multiple Fluorescent Properties and Response to Hydrogen Peroxide of Developed Benzothiazole Derivatives. Available at SSRN: https://ssrn.com/abstract=4456141 or http://dx.doi.org/10.2139/ssrn.4456141