Fluorescent chemosensors with aggregation induced emission enhancement (AIEE) emerge as promising tools in the field of sensing materials. Herein, we report the design, synthesis and applicability of a Schiff base chemosensor 1‐(benzo[1,3]dioxol‐4‐ylmethylene‐hydrazonomethyl)‐naphthalen‐2‐ol (Hbdhn) of AIE characteristics that exhibits highly effective and selective response towards Zn2+. The sensing effect of Hbdhn was evaluated by means of absorption/emission spectra and corresponding underlying photophysical mechanisms were proposed based on extensive quantum‐chemical (TD)DFT calculations. The aggregated states in different DMSO/H2O ratios and in a presence of Zn2+ were examined by fluorescence lifetime measurements, dynamic light scattering and scanning electron microscopy studies. The bioimaging abilities of Hbdhn were evaluated for Zn2+ in HepG2 cancer cells. The results demonstrate instant, stable in time and reproducible, colorimetric turn‐on response with superb selectivity and sensitivity of Hbdhn towards Zn2+, based on chelation enhanced fluorescence mechanism. AIEE improves further Hbdhn properties, leading to strong, long‐lived fluorescence, with appearance of rod‐like particles, in 90 % of water in DMSO and only 10 % of water in DMSO in the presence of Zn2+. All these features combined with successful biomaging studies make Hbdhn one of the most promising candidate for practical applications among recently proposed related systems.
A pyridine–pyrazole based fluorescence turn-on chemosensor provides access to selective detection of Al3+ in solution as well as in HepG2 living cells.
A reaction of N,N-bis(3-methoxysalicylidene) diethylenetriamine (H2Vd) and Zn(NO)·6HO, ZnBr, ZnI and Cd(NO)·4HO in a methanol solution led to zinc and cadmium complexes of different nuclearities, [Zn(Vd·H)(X)]·CHOH (X = NO, Br, I) [1a, 1b and 1c] and Cd(Vd)(NO) (2). In 1(a-c), two H2Vd ligands bridge the two metal centers whereas in 2, they provide sideways support to two terminal Cd ions, providing an all-oxygen envelope to the central Cd ion. All four compounds were characterized by elemental analysis, FT-IR spectroscopy and single crystal X-ray diffraction analysis. Complexes 1(a-c) exhibit dinuclear structures, whereas 2 exhibits a nearly linear trinuclear structure. The structural differences among these complexes are attributable to various coordination modes and flexible configurations of the H2Vd ligand. The ligand H2Vd is an excellent probe for sensing Zn in solution, whereas complexes 1(a-c) are able to selectively detect pyrophosphate (PPi) in aqueous medium. The structure of the pyrophosphate (PPi) complex has been proposed using DFT calculations and the selectivity is due to the unique ability of this anion to simultaneously coordinate to both the Zn metal centers. The anticancer activity of complexes 1(a-c) was also explored.
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