Compound 1 bearing urea and viologen groups has been designed and synthesized.It could be used as a colorimetric receptor for dicarboxylate anions due to the significant color changes of the solution upon the addition of dicarboxylates.More importantly,the color changes were related to the chain lengths of the dicarboxylates tested.UV-vis,＇H NMR and HRMS studies demonstrated that receptor 1 utilized hydrogen bonds and electrostatic interactions to form 1：1 stoichiometry complexes with these anions.In addition,the generation of cation radical 1＇ during the complexation process was also detected by EPR.
A series of novel imidazolium based ionic liquids containing the urea moiety were designed and synthesized for anion recognition. 1-Ethylurea-3-methylimidazolium acetate ([Eumim]OAc) was used as the receptor for the halides and complex anions (BF4-, PF6-, BPh4-). 1H NMR spectra showed that the urea protons and imidazolium C(2) proton of the receptor ([Eumim]OAc) moved upfield on addition of various anions. A Job plot showed that the [Eumim]OAc receptor formed a 1:1 complex with BPh4-. X-ray diffraction analysis and the molecular modeling study revealed that the conformations of [Eumim]OAc and [Eumim]BPh4 were different. The conformational change of the cation was caused by anion exchange, and may provide an alternative to current methods for recognition of anions.
Benzimidazolium-based receptors 1-3 were designed and synthesized. On the basis of fluorescence, UV-Vis, and 1H NMR spectroscopic studies, and X-ray single crystal structure analysis, it was confirmed that the receptor 1 displays strong (C-H)+···X, N-H···X hydrogen bonds and charge-charge interactions with anions. More importantly, these investigations demonstrated that the charged (C-H)+ benzimidazolium and urea moieties play a synergistic role in anion recognition.
