Design and development of 5-aminoindan-based chemosensor for Hg2+ detection and cytotoxicity evaluation

Abstract

Novel 5-aminoindan-based azo derivatives (3a–e) containing an indane moiety were designed and synthesized via diazotization and coupling reactions. The synthesized compounds were characterized by UV–Vis, FT-IR, 1 H NMR, and LC–MS spectral studies. Their electronic properties were analysed using density functional theory (DFT) calculations. The In vitro cytotoxic activity of compounds 3c and 3d was evaluated against the A431 human skin carcinoma cell line using the MTT assay, and both compounds exhibited measurable cytotoxic effects. The interaction of the synthesized azo dyes with Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Hg 2+ , and Pb 2+ ions was investigated by UV–Vis and fluorescence spectroscopy. Among the series, compound 3d showed a distinct response toward Hg 2+ ions with a limit of detection of 1.62 × 10 −6 M. Molar ratio analysis indicated the formation of a coordination complex between 3d and Hg 2+ with a 2:1 ligand-to-metal stoichiometry. The combined experimental and computational data provide insight into the sensing and biological behaviour of the 5-aminoindan-based azo framework.