A julolidine-coupled benzoxazole-based fluorescent chemosensor (BPOZ) is designed and developed to investigate the different target analyte interactions spectroscopically. Based on the 'off-on-off' photoluminescence mechanism, the as-prepared BPOZ is used for sequentially detecting Zn 2 + and HSO 4À ions, respectively. The UV-visible absorption and photoluminescence spectral behavior is intramolecular charge transfer (ICT) in nature. When Zn 2 + ions bind with BPOZ, its fluorescence is significantly enhanced at 512 nm due to chelation-enhanced fluorescence. A green color emission is also visible under 365 nm UV light exposure, which is also confirmed by the color chromaticity diagram. Chelation-enhanced photoluminescence is also manifested in the lifetime decay analysis. Further, it is well supported by different spectroscopic techniques and DFT analysis. In the presence of HSO 4À ions, photoluminescence of the Zn 2 + chelated BPOZ complex is significantly reduced, rebirthing the free BPOZ. The detection limit of BPOZ for Zn 2 + and Zn 2 + chelated BPOZ complex towards detecting Zn 2 + and HSO 4À ions is established to be in the order of nM and μM range, respectively, in the solution phase. Among the various explosive nitroaromatic compounds, picric acid (PA) quenched the emission of the Zn 2 + chelated BPOZ complex, and the quenching mechanism is found to be both static and dynamic in nature. Using these chemically prearranged inputs and optical outputs, two inputs, INHIBIT, and three inputs, combinational logic gates have been constructed. The BPOZ chemosensor and Zn 2 + chelated BPOZ complex are also employed to map Zn 2 + ions and PA in the living cell. The performance of the BPOZ chemosensor and Zn 2 + chelated BPOZ complex toward Zn 2 + ions and PA proved that it could be exploited as a signal tool for environmental and biological samples.