Synthesis of new chromogenic sensors containing thiourea and selective detection for F–, H2PO4–, and Ac– anions

Abstract

Two new chromogenic sensors 1-(2-hydroxyphenyl)-3-(4-nitrophenyl)thiourea 1 and 1-(3-hydroxypyridin-2-yl)-3-(4-nitrophenyl)thiourea 2 bearing nitrophenyl and thiourea groups were designed and synthesized by one-step procedure and characterized through 1H NMR, 13C NMR, FTIR, and MS. The anion recognition property of the receptors was studied via naked-eye detection, UV–vis, and 1H NMR. Based on the existence of amino gen and hydroxyl moieties in receptors, receptors 1 and 2 exhibit obvious selectivity by the redshift of UV–vis signals, colour changes through naked-eye detection, and binding effects for F–, H2PO4–, and Ac–. Surprisingly, the detection limits of receptor 1 for F– and Ac– were calculated to be 5.45 × 10−7 and 2.11 × 10−7 (mol/L)−1, respectively, which indicated that F– and Ac– can be identified with high sensitivity by receptor 1. Besides, simple “test strips” were developed and were used as sensors for recognition of F–, H2PO4–, or Ac– in DMSO solution. Lastly, the mechanisms of the recognition process were studied through DFT calculation and 1H NMR titration.