Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1090-1096.DOI: 10.6023/cjoc201411030 Previous Articles     Next Articles



卓继斌a, 晏希泉a, 王小雪a, 谢莉莉a,b, 袁耀锋a,b   

  1. a 福州大学化学学院 福州 350116;
    b 能源与环境光催化国家重点实验室 福州 350002
  • 收稿日期:2014-11-16 修回日期:2014-12-09 发布日期:2015-01-05
  • 通讯作者: 袁耀锋
  • 基金资助:


Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors

Zhuo Jibina, Yan Xiquana, Wang Xiaoxuea, Xie Lilia,b, Yuan Yaofenga,b   

  1. a College of Chemistry, Fuzhou University, Fuzhou 350116;
    b State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350002
  • Received:2014-11-16 Revised:2014-12-09 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).

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