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 Zn . 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/H O ratios and in a presence of Zn were examined by fluorescence lifetime measurements, dynamic light scattering and scanning electron microscopy studies. The bioimaging abilities of Hbdhn were evaluated for Zn 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 Zn , 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 Zn . All these features combined with successful biomaging studies make Hbdhn one of the most promising candidate for practical applications among recently proposed related systems.