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A pyridine based imine-linked chemosensor has been synthesized and evaluated its binding affinity with library of transition metal ions. It has prominent selectivity towards Pb 2+ among other metal ions in DMF/H 2 O (9:1, v/v) solvent system. The 1:1 stoichiometric was confirmed by job's plot and has a binding constant (K a ) = 5.142 × 10 3  M -1 on fluorescence. A B3LYP/6-31G and B3LYP/LanL2DZ basis sets were employed for optimization of 3 and 3.Pb 2+ .