双核开链茂铁咪唑受体的合成与阴离子识别研究
收稿日期: 2014-11-16
修回日期: 2014-12-09
网络出版日期: 2015-01-05
基金资助
国家自然科学基金(Nos.21202019,21372043)、国家基础科学人才培养基金(No.J1103303)资助项目.
Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors
Received date: 2014-11-16
Revised date: 2014-12-09
Online published: 2015-01-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21202019, 21372043), and the National Science Foundation for Fostering Talents in Basic Research of China (No.J1103303).
卓继斌 , 晏希泉 , 王小雪 , 谢莉莉 , 袁耀锋 . 双核开链茂铁咪唑受体的合成与阴离子识别研究[J]. 有机化学, 2015 , 35(5) : 1090 -1096 . DOI: 10.6023/cjoc201411030
The design and synthesis of artificial receptors capable of binding and sensing anions have been widely explored in the field of host-guest chemistry. Herein, a series of acyclic ferrocene-based imidazolium receptors 3a~3e were designed and synthesized. All the receptors were prepared by reactions of 1-(ferrocenylmethylene)imidazole 1 with corresponding dibromides in solvent under refluxing, followed by anion exchanges with NH4PF6. The structures of all the products were determined by IR, 1H NMR, 13C NMR, MS and elemental analysis. The crystal structure 3e was confirmed by X-ray crystallography, and it was clear that molecules were linked by C—H…F hydrogen bonds interactions. The interaction between these receptors and various anions was studied by electrochemical measurements and 1H NMR spectroscopy. The receptors 3a~3e were proven to be highly selective and sensitive to F-. 1H NMR titrations demonstrated that the receptors and anions form 1:1 complex, and the receptors displayed a strong (C—H)+…X- in anion recognition. Receptor 3c was the most effective receptor to bind with fluoride ion compared to the others.
Key words： ferrocene; acyclic; imidazolium; synthesis; anion recognition
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