A carboethoxy quinoline-Derived Schiff base chemosensor: Crystal structure, selective Hg2+ ion detection and its computational study

Abstract

Environmental monitoring of mercury (Hg²⁺) ions has become increasingly important as a result of their detrimental effects on biological organisms at all levels. To recognize toxic metal ions, utmost effort has been devoted to developing new materials that are highly selective, ultra-sensitive, and provide rapid response. In this context, a new chemosensor, 2-imino [N - (N-amido phenyl)]-6-methoxy-3-carbethoxy quinoline (L), has been synthesized by combining 2-formyl-6-methoxy-3-carbethoxy quinoline and benzhydrazide and it has been extensively characterized by NMR, FTIR, ESI-Mass and SCXRD analysis. Probe L has excellent specificity and sensitivity toward Hg²⁺ ions in semi-aqueous solutions, with a detection limit of 0.185 μM, regardless of the presence of other interfering cations. Chromogenic behavior was demonstrated by the L when it changed the color of the solution from colorless to light yellow, a change that can be observed visually. The probe L forms a 1:1 stochiometric complex with an estimated association constant (K_a) of 6.74 × 10⁴ M^-1. The ¹H NMR change and density functional theory calculations were analyzed to improve our understanding of the sensing mechanism. Also, an inexpensive and simple paper-based test kit has been developed for the on-site detection of mercury ions in water samples.

Keywords: Chemosensors; Crystal structure; DFT study; Mercury; Quinoline.