The aryl-amine containing azacrown ether ring and alkyl-chloro boradiazaindacene (Bodipy) were synthesized by the Schiff base condensation. The absorption and emission of a novel Schiff base derivative (based on azacrown–Bodipy) were performed in presence of different cations such as Zn2+, Ga3+, Pb2+, Hg2+, NH4+ Ca2+, Cu2+, Na+, Ni2+, Cd2+ and Cr3+. The complexation property of the Schiff base was studied in dimethylformamide (DMF) by interacting azacrown-ether group and transition metal nitrates–ammonium chloride. The electrochemical behavior of the Schiff base has also been investigated by cyclic voltammetry. All experimental results indicated that the new compound acts as a selective ratiometric chemosensor for Hg2+.