Chromone functionalized pyridine chemosensor for cupric ions detection

Abstract

A new Schiff base 2-ethoxy-3-{[(6-{[(2-ethoxy-4-hydroxy-2H-chromen-3-yl)methylidene]amino}pyridine-2-yl)imino]methyl}–2H-chromen-4-ol (CD) was synthesized as a result of the condensation of 2,6-diaminopyridine and 3-formyl chromone in 1:2 M ratio and used for cupric ions detection and characterized through FTIR, HRMS and 1H NMR spectral techniques. The sensing capability of Schiff base for cupric ions as compared to other transition metal ions was examined by absorbance and emission studies. A considerable decrease in emission intensity appeared in Schiff base in the case of cupric ions while irrelevant changes were examined for the rest of the ions. The binding stoichiometry was obtained as 1:2 for CD: Cu2+ complex intended from the job’s plot which was confirmed through HRMS spectral technique. DFT calculations were carried for the confirmation of structural relationships and absorption–emission data. The Regression coefficient, Limit of detection, and Association constant were obtained as 98.7%, 1.2 × 10-6 M, and 3.26 × 104 M−1 respectively using Benesi-Hildebrand (B-H) equation. The sensing power of Schiff base CD to recognize cupric ions was unaltered by the addition of the rest of metal ions, which was authenticated through interference studies. Schiff base CD and its complex with cupric ions were found stable over an extensive time period as revealed by time-reliant studies. The data collected by pH studies revealed that the preferred pH range for detecting cupric ions by Schiff base CD was 6 to 11. The Schiff base was finally utilized for sensing cupric ions in a variety of spiked samples of water like canal water, tap water, groundwater, distilled water.