Abstract
Abstract Although a variety of fluorescence based chemosensors have been utilized for selective detection of Zn2+, pyridoxal containing simple Schiff bases still remained less explored. Here, we combine pyridoxal hydrochloride and 1,2-diaminocyclohexane to generate a new sensor molecule, H4PydChda [5-Hydroxymethyl-4-({2-[5-hydroxymethyl-2-methylpyridin-3-hydroxy-4-ylethylene)-amino]-cyclohexylimino}-methyl-2-methylpyridin-3-ol]. Chemosensor H4PydChda exhibits selective turn-on type response in presence of Zn2+ in ethanol-water mixture at physiological pH. Appreciable fluorescence enhancement occurs upon addition of Zn2+ to H4PydChda as a result of inhibited C N isomerisation and excited state intramolecular proton transfer (ESIPT) leading to efficient chelation enhanced fluorescence (CHEF). The relevant properties, including reversibility, life time measurements and detection limit have been determined for the sensor system. The experimental and theoretical supports in terms of 1H and 13C NMR spectroscopy and DFT/TDDFT study are provided to establish the binding mode of H4PydChda to Zn2+. H4PydChda was employed as a sensor for detection of Zn2+ in Human gastric adenocarcinoma (AGS) cells. Moreover, the resulting probe-Zn2+complex shows convincing phosphatase activity (kcat = 21.59 s−1), opening a promising avenue for further research.
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