Synthesis of Two Anion Receptors of 1H-Imidazo[4,5-f][1,10]phenanthroline Derivatives and Their Recognition Properties

doi:10.3969/j.issn.0251-0790.2012.06.020

Abstract

Abstract: Anion play important roles in a wide range of chemical, biological and environmental processes. So anion binding and sensing became an active research field in supramolecular chemistry with potential applications in biomedical and environmental monitoring, anion exchange as well as anion transport. Artificial neutral receptors for anions are designed and synthesized in which color metric sensors are paid a good deal of attention for they could efficiently change their photo physical properties in the presence of anions. Imidazole and phenol are recently used in the design of neutral receptors for anions due to their ability to act as H-bond donors. Two anion receptors of 1H-imidazo[4,5-f][1,10]phenanthroline derivatives, 2-(2-hydroxyphenyl)-1H-imidazo[4,5-f][1,10]phenan-throline(1) and 2-(2-hydroxy-5-bromophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline(2) were designed and synthesized, and the structure of compound 2 was confirmed by single crystal X-ray diffraction analysis. Anion sensing and the mechanism studies were carried out by UV-Vis spectrophotometric titration and ¹H NMR titration. The receptors exhibited sensing towards CH₃COO^-, F^- and H₂PO₄^- with color of the solution changed from pale yellow to yellow, and weakly sensing towards Cl^- with inconspicuous response towards Br^- and I^- in DMSO. The receptors formed hydrogen bond supramolecular with anions F^-, H₂PO₄^- and CH₃COO^- as 1: 1 within[receptor]/[anion]=1. As flowed with the molar ratio exceeded 1, the proton of 1H-imidazo deprotoned and linked with the anion. The receptors formed hydrogen bond supramolecular with Cl^-.

Key words: 1H-Imidazo[4,5-f][1,10]phenanthroline derivative, Crystal structure, Anion recognition

CLC Number:

O626.23

TrendMD:

CHEN Hua-Mei, YUE Fan, LIN Hai, LIN Hua-Kuan. Synthesis of Two Anion Receptors of 1H-Imidazo[4,5-f][1,10]phenanthroline Derivatives and Their Recognition Properties[J]. Chem. J. Chinese Universities, 2012, 33(06): 1239.

References

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