Abstract
A novel Schiff bases of 2-((2-aminophenylimino)methyl)-3-phenyl-4(3H)-quinazolinone (3a), 2-((2-aminophenylimino)methyl)-3-(4-tolyl)-4(3H)-quinazolinone (3b), and 2-((2-aminophenylimino)methyl)-3-(4-anisyl)-4(3H)-quinazolinone (3c) were synthesized and characterized by FTIR, NMR, and elemental analysis. In an aqueous solution at pH 8, the quinazolinone derivatives (3a–c) show remarkable selectivity and sensitivity towards Cu2+ ions over other common metal ions. The molar ratio plot confirms a 2:1 stoichiometry complex formation between 3a-c compounds and Cu2+. In addition, the binding constants (Kd) were calculated using Lineweaver-Burk plots and were found to be 2.45×106, 7.80×104 and 4.17×105 M−1 for 3a, 3b, and 3c, respectively. The detection limits were 0.04, 0.16 and 0.10 µmol L−1 for 3a, 3b, and 3c, respectively with a good linearity in the range of 0.2–2.0 µmol L−1. The quenching mechanism of 3a–c toward Cu2+ ions is assigned to the reverse photoinduced electron transfer. The synthesized sensors are applied to detecting Cu2+ions in sea water samples. The developed sensors were successfully used as test strips for fluorescence detection of Cu2+ ions.
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