A novel Schiff base 1-((E)-((E)-(4-(benzyloxy) benzylidene) hydrazono) methyl) naphthalen-2-ol [BBHN] having aggregation induced emission enhancement (AIEE) behaviour in DMSO/water mixture have been designed, synthesized, and characterized using spectral methods. The aggregate of BBHN shows relatively high Cu2+ ion selectivity and sensitivity among various metal ions through fluorescence “turn off” response with a very high detection limit of 35.52 nM and a quenching constant value of 2.58 × 108 M−1. These observations suggest that the synthesized Schiff base, BBHN could effectively function as a nano sensor for the detection of Cu2+ ion in aqueous media. The fluorescence quenching behaviour of BBHN in the presence of Cu2+ ions is taking place through dynamic quenching which was evident from the steady state fluorescence lifetime measurement study.