Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors

doi:10.6023/cjoc201411030

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

ARTICLE

双核开链茂铁咪唑受体的合成与阴离子识别研究

卓继斌^a, 晏希泉^a, 王小雪^a, 谢莉莉^a,b, 袁耀锋^a,b

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 E-mail:yaofeng_yuan@fzu.edu.cn
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

Zhuo Jibin^a, Yan Xiquan^a, Wang Xiaoxue^a, Xie Lili^a,b, Yuan Yaofeng^a,b

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).

1. Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors.PDF(945KB)

Abstract

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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Zhuo Jibin, Yan Xiquan, Wang Xiaoxue, Xie Lili, Yuan Yaofeng. Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors[J]. Chin. J. Org. Chem., 2015, 35(5): 1090-1096.

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双核开链茂铁咪唑受体的合成与阴离子识别研究

Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors

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