Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, College of Light Industry and Food, Nanjing Forestry University, Nanjing, 210037, China.
Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, MI 48502, USA.
Dalton Trans. 2020 Nov 10;49(43):15299-15309. doi: 10.1039/d0dt02888f.
A highly sensitive AIE fluorescent chemosensor, N'-((4'-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-5,7-methanoindazol-3-yl)-[1,1'-biphenyl]-4-yl)methylene)picolinohydrazide (PBPHS), for the detection of Hg2+ and Cu2+ ions in near 100% aqueous solution was developed based on the renewable β-pinene derivative nopinone. The probe PBPHS was designed and synthesized via a four reaction steps, including condensation, cyclization, Suzuki coupling reaction, and Schiff-base reaction. PBPHS could recognize Hg2+ and Cu2+ over other competitive metal ions via specific complexation ability towards them. The detection limits of PBPHS for Hg2+ and Cu2+ were 15 nM and 17 nM, respectively. The fluorescent probe PBPHS could also be utilized to detect S2- and Hg2+/Cu2+ reversibly for five cycle. Moreover, the different binding mechanisms of PBPHS with Hg2+ and Cu2+ were confirmed by HRMS analysis, 1H NMR titration, DFT calculation, and molecular logic gate. Furthermore, the probe PBPHS was applied for the analysis of real water and soil samples and living HeLa cells and zebrafish bioimaging.
一种高灵敏度的聚集诱导发射荧光化学传感器，N'-((4'-(6,6-二甲基-4,5,6,7-四氢-1H-5,7-甲并吲哚-3-基)-[1,1'-联苯]-4-基)亚甲基)吡啶甲酰肼(PBPHS)，是基于可再生的β-蒎烯衍生物诺蒎酮开发的，用于在近 100%的水溶液中检测 Hg2+和 Cu2+离子。探针 PBPHS 通过包括缩合、环化、Suzuki 偶联反应和希夫碱反应在内的四个反应步骤设计和合成。PBPHS 通过对 Hg2+和 Cu2+的特殊络合能力，能够识别 Hg2+和 Cu2+，而不会受到其他竞争金属离子的干扰。PBPHS 对 Hg2+和 Cu2+的检测限分别为 15 nM 和 17 nM。荧光探针 PBPHS 还可用于检测 S2-和 Hg2+/Cu2+，并可进行五次循环的可逆检测。此外，通过高分辨率质谱分析、1H NMR 滴定、DFT 计算和分子逻辑门，证实了 PBPHS 与 Hg2+和 Cu2+的不同结合机制。此外，探针 PBPHS 还用于分析实际水样和土壤样品以及活 HeLa 细胞和斑马鱼的生物成像。
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