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The turn-off fluorescent sensors based on thioether-linked bisbenzamide for Fe3+ and Hg2+
- Lv, Hehong, Ren, Ziqi, Liu, Heng, Zhang, Ganbing, He, Hanping, Zhang, Xiuhua, Wang, Shengfu
- Tetrahedron 2018 v.74 pp. 1668-1680
- aromatic compounds, chemical reactions, chemical structure, fluorescence, geometry, iron, mercury, nuclear magnetic resonance spectroscopy, titration
- Some dibenzamide derivatives with a thioether linker were designed, synthesized and characterized. The specific responses to Hg²⁺ and Fe³⁺ were investigated by fluorescence. According to fluorescence titration, the Job plot, ¹H NMR, and ESI-mass analysis, the derivative with mono-hydroxyl substituent (1b) on the aromatic ring has high selectivity for Fe³⁺ ion with the formation of 1:1 1b-Fe³⁺ complexes. The specificity of 1c for Hg²⁺ could be switched by swapping the substituent from hydroxyl to amino, and a 1:2 (1c-Hg²⁺) complex was formed. Along with the obtained results, density functional theory (DFT) and natural bond orbital (NBO) analyses, Time-dependent (TD) DFT and natural transition orbital (NTO) analyses were employed to explore the geometric structures, properties and possible mechanisms.