Nopinone-based AIE active dual-functional fluorescent chemosensor for Hg2+ and Cu2+ and its environmental and biological applications
A high 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 detecting Hg2+ and Cu2+ ions in near 100% aqueous solution was developed based on the renewable β-pinene derivatives nopinone. The probe PBPHS was designed and synthesized by four steps reactions 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 also could be utilized to detect S2- and Hg2+/Cu2+ reversibly with five cycle periods. Moreover, we confirm the different binding strategies of PBPHS with Hg2+ and Cu2+ by HRMS analysis, 1 H NMR titration, DFT calculation, and molecular logic gate. Furthermore, the probe PBPHS was applied in real water and soil samples analysis and living HeLa cells and zebrafish bioimaging.