Chemical Research in Chinese Universities ›› 2025, Vol. 41 ›› Issue (1): 79-85.doi: 10.1007/s40242-024-4145-y

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A Dibenzo-18-crown-6-based Symmetric Dual-coumarin Lead Ion Fluorescent Probe and Its Imaging in Living Cells

LIU Xiaolei1,2,3, GONG Chongzhen4, PENG Xiujing2, SUN Guoxin2, YAO Wei2, CHU Yongjie5, ZHANG Tianyong1   

  1. 1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
    2. Institute for Smart Materials and Engineering, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, P. R. China;
    3. Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China;
    4. Zaozhuang No. 20 Middle School, Zaozhuang 277011, P. R. China;
    5. Shandong Zhongcheng Test and Testing Co., Ltd., Jinan 250100, P. R. China
  • Received:2024-06-18 Online:2025-02-01 Published:2025-01-18
  • Contact: LIU Xiaolei,ism_liuxl@ujn.edu.cn;YAO Wei,stu_yaow@ujn.edu.cn;ZHANG Tianyong,tyzhang@tju.edu.cn E-mail:ism_liuxl@ujn.edu.cn;stu_yaow@ujn.edu.cn;tyzhang@tju.edu.cn
  • Supported by:
    This work was supported by the Sub-project of the National Key R&D Project of China (No. 2022YFC3902701-2), the Opened Foundation of the Key Laboratory of Molecular and Nano Probes, Ministry of Education, China (No. 2020KLMNP03), the Science and Technology Program of University of Jinan, China (No. XKY2066).

Abstract: Herein, a turn-on fluorescent probe for the detection of lead ions was developed using 7-diethylaminocoumarin as the fluorophore and dibenzo-18-crown-6 as the recognition unit. The response performance to lead ions was systematically studied. The probe showed specific selectivity and high sensitivity to lead ions, with fluorescence intensity at 496 nm increasing linearly with lead ion concentration (R2=0.995) over the range of 1.0×10-7―1.0×10-6 mol/L, and an LOD of 11.4 nmol/L. Job’s plot revealed that the probe forms a 1:1 stoichiometry complex with lead ions during the recognition process. Furthermore, the sensing mechanism of the probe was confirmed by density functional theory calculations, indicating that the recognition mechanism is based on photoinduced electron transfer (PET). The introduction of lead ions blocks PET, resulting in fluorescence enhancement. Finally, it was applied in the detection of practical water samples and bioimaging, demonstrating high application value in the field of chemosensors.

Key words: Coumarin, Dibenzo-18-crown-6, Fluorescent probe, Pb2+, Bioimaging