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Author: search.filters.author.Daengngern, RathawatSubject: search.filters.subject.Sensor

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    The synergy of CHEF and ICT toward fluorescence ‘turn-on’ probes based on push-pull benzothiazoles for selective detection of Cu2+ in acetonitrile/water mixture
    (2021-06-15)
    Nootem, Jukkrit
    ;
    Daengngern, Rathawat
    ;
    Sattayanon, Chanchai
    ;
    Wattanathana, Worawat
    ;
    Wannapaiboon, Suttipong
    New push-pull schiff base ligands based on benzothiazole (BZ) unit were developed for the selective detection of Cu<sup>2+</sup> through fluorescence ‘turn-on’ mechanism. These derivatives with electron withdrawing trifluoromethyl (-CF<inf>3</inf>) and cyano (-CN) substituents (BZ2 and BZ3) demonstrated a prominent fluorescence enhancement upon copper ion binding which could be the results from the synergistic effect between the chelation-enhanced fluorescence (CHEF) and the intramolecular charge transfer (ICT) processes. In addition, these compounds displayed 1:1 binding with Cu<sup>2+</sup> with low limits of detection of 0.77 μM and 0.64 μM for BZ2 and BZ3, respectively, in acetonitrile-water (3:1 v/v) media. The electronic and photophysical properties of these BZ ligands and the copper ion complexes were modelled by the density functional theory (DFT) and the time-dependent density functional theory (TD-DFT) calculations, respectively. Analysis of X-ray absorption spectra probed at Cu K-edge of Cu<sup>2+</sup>-BZ mixtures revealed the complex formation of BZ ligands with the targeted Cu<sup>2+</sup> and confirmed the non-centrosymetric structures of the complexes as predicted by the DFT calculation. The electron density distributions of the HOMO-LUMOs in the computational results as well as large stokes shifts of the ligand-metal complexes in the experimental data confirmed the strong ICT effect after Cu<sup>2+</sup> binding which is a key process promoting fluorescence ‘turn-on’ mechanism.