A novel dual mode viscosity sensitive and AIE active fluorescent chemosensor based on naphthalene coupled pyrene (NCP) moiety has been designed and synthesized for selective detection of OCl¯ and Cu2+. In non-viscous media, NCP exhibited weak fluorescence but with the increase in viscosity by using various proportion of glycerol results the enhancement of fluorescence intensity at 461 nm with 6-fold increase of fluorescence quantum yield, which could be utilized for quantitative determination of viscosity. Intriguingly, NCP exhibited novel AIE characteristics in H2O-CH3CN mixtures at high water content with size and growth process of particles in different volume percentage of water and CH3CN mixtures, which was investigated using fluorescence, DLS study and SEM images. Interestingly this probe can also be effective to employ as dual mode fluorescent probe for light up fluorescent detection of OCl¯ and Cu2+ at different emission wavelengths at 439 nm and 457 nm by chemodosimetric and chelation pathways respectively. The fast-sensing ability of NCP towards OCl¯ has been shown by lower detection limit at 0.546 μM and the binding affinity of NCP with Cu2+ has been proved by lower detection limit at 3.97 μM and high binding conastnt at 1.66×103 M-1. The sensing mechanism of NCP with OCl¯ and Cu2+ has been verified by UV-vis, Fluorescence, 1H-NMR analysis, mass spectra, DFT study and Jobs plot analysis. For the practical applications, the binding of NCP with OCl¯ and Cu2+ has been capitalized through dipstick method as well as cell imaging study in physiological medium by using green gram seeds.

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