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

• Published in: Supramolecular chemistry Vol. 32; no. 7; pp. 403 - 413
• Main Authors: Pati, Chiranjit, Chattopadhyay, Asoke P., Ghosh, Kumaresh
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis 02.07.2020; Taylor & Francis Ltd
• Subjects: Anions; Calcium ions; Chelating agents; Chelation; Color; Copper; copper sensing and Colorimetric detection; cyanide sensing; Detection; Fluorescence; fluoride sensing; Mercury (metal); mercury sensing; Naphthalimide derivative; NMR; Nuclear magnetic resonance; Selectivity
• ISSN: 1061-0278; 1029-0478
• DOI: 10.1080/10610278.2020.1749628

Diaminomalenonitrile-linked naphthalimide 1 has been designed and synthesised. It shows selective sensing of F − , CN − , Cu 2+ and Hg 2+ under different experimental conditions. While compound 1 in CH 3 CN exhibits colour change from yellow to greenish blue or green in the presence of F − , AcO − , CN − and H 2 PO 4 − , it shows a colour change from yellow to light green selectively in presence of CN − in aqueous CH 3 CN. The selectivity of 1 for F − in pure CH 3 CN is achieved by using Ca 2+ ion as chelating agent. Besides anion sensing, the probe exhibits different colour attributes towards Hg 2+ and Cu 2+ ions in aqueous CH 3 CN. While the yellowish solution of 1 is discharged to almost colourless in presence of Cu 2+ ions, a light red colour is observed in the presence of Hg 2+ 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.