Premium
A benzimidazole‐based chromogenic anion receptor
Author(s) -
Yu Ming,
Lin Hai,
Zhao Guanhua,
Lin Huakuan
Publication year - 2006
Publication title -
journal of molecular recognition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.401
H-Index - 79
eISSN - 1099-1352
pISSN - 0952-3499
DOI - 10.1002/jmr.810
Subject(s) - benzimidazole , chromogenic , halide , hydrogen bond , chemistry , selectivity , receptor , ion , fluoride , crystal structure , stereochemistry , molecule , crystallography , inorganic chemistry , organic chemistry , biochemistry , chromatography , catalysis
Abstract A benzimidazole‐based anion receptor 1 has been designed and synthesized. The structure of 1 is confirmed through single crystal X‐ray diffraction analysis. Anion‐binding studies carried out using 1 H NMR and UV–visible revealed that this compound exhibits selective recognition toward F − over other halide anions. The highest selectivity for F − among the halides is attributed mainly to the strongest hydrogen‐bond interaction of the receptor with F − ; in addition, the higher match in geometry between the receptor and F − also plays a role in the selective recognition of the receptor for F − . Receptor 1 (1 × 10 −5 M) shows dramatic color change from light‐yellow to red in the presence of tetrabutylammonium fluoride (TBAF) (1 × 10 −5 M). Moreover, F − ‐induced color changes remain the same even in the presence of a large excess of Cl − , Br − , I − . Copyright © 2006 John Wiley & Sons, Ltd.