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Diamino malenonitrile-linked naphthalimide in selective sensing of F-, CN-, Hg2+ and Cu2+ under different experimental conditions

ABSTRACT Diaminomalenonitrile-linked naphthalimide 1 has been designed and synthesised. It shows selective sensing of F−, CN−, Cu2+ and Hg2+ under different experimental conditions. While compound 1 in CH3CN exhibits colour change from yellow to greenish blue or green in the presence of F−, AcO−, CN− and H2PO4 −, it shows a colour change from yellow to light green selectively in presence of CN− in aqueous CH3CN. The selectivity of 1 for F− in pure CH3CN is achieved by using Ca2+ ion as chelating agent. Besides anion sensing, the probe exhibits different colour attributes towards Hg2+ and Cu2+ ions in aqueous CH3CN. While the yellowish solution of 1 is discharged to almost colourless in presence of Cu2+ ions, a light red colour is observed in the presence of Hg2+ ions. The interaction study has been performed by NMR, UV-vis, fluorescence and mass spectroscopic techniques. A theoretical study has been invoked to understand the deprotonation of 1 that occurs in presence of basic anions. Graphical Abstract