Chinese Journal of Organic Chemistry >
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).
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
Zhuo Jibin , Yan Xiquan , Wang Xiaoxue , Xie Lili , Yuan Yaofeng . Synthesis and Anion Recognition of Acyclic Ferrocene-Based Imidazole Receptors[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1090 -1096 . DOI: 10.6023/cjoc201411030
[1] (a) Maeda, H.; Shirai, T.; Bando, Y.; Takaishi, K.; Uchiyama, M.; Muranaka, A.; Kawai, T.; Naito, M. Org. Lett. 2013, 15, 6006. (b) Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262. (c) Huang, Z. B.; Liu, X. C.; Hu, M. H.; Lin, W.; Shi, D. Q. Chin. J. Org. Chem. 2014, 34, 382 (in Chinese). (黄志斌, 刘学成, 胡明华, 林伟, 史达清, 有机化学, 2014, 34, 382.)
[2] (a) Wade, C. R.; Broomsgrove, A. E.; Aldridge, S.; Gabbai, F. P. Chem. Rev. 2010, 110, 3958. (b) Zhang, D. W.; Yang, H. Q.; Martinez, A.; Jamieson, K.; Dutasta, J. P.; Gao, G. H. Chem. Eur. J. 2014, 20, 1. (c) Liu, R. Y.; Yong, X.; Yang, X. D.; Yan, Y. S.; Lu, X. W.; Qu, J. Q. Chin. J. Org. Chem. 2014, 34, 561 (in Chinese). (刘瑞源, 勇雪, 杨小东, 严轶琛, 路新卫, 瞿金清, 有机化学, 2014, 34, 561.)
[3] Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
[4] Niu, H. T.; Yin, Z.; Su, D.; Niu, D.; Ao, Y.; He, J.; Cheng, J. P. Tetrahedron 2008, 64, 6300.
[5] Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355.
[6] (a) Su, Z. M.; Ye, H. M.; Zhu, X. X.; Xie, L. L.; Bai, S.; Yuan, Y. F. J. Organomet. Chem. 2014, 750, 162. (b) Zhuo, J. B.; Zhang, C. Y.; Lin, C. X.; Bai, S.; Xie, L. L.; Yuan, Y. F. J. Organomet. Chem. 2014, 763~764, 34.
[7] Cao, Q. Y.; Han, Y. M.; Yao, P. S.; Fu, W. F.; Xie, Y.; Liu J. H. Tetrahedron Lett. 2014, 55, 248.
[8] (a) Beer, P. D.; Hayes, E. J. Coord. Chem. Rev. 2003, 240, 167. (b) Caballero, A.; Martínez, R.; Lloveras, V.; Ratera, I.; Vi-dal-Gancedo, J.; Wurst, K.; Tárraga, A.; Molina, P.; Veciana, J. J. Am. Chem. Soc. 2005, 127, 15666. (c) Cao, Q. Y.; Zhang, J. F.; Ren, W. X.; Choi, K.; Kim, J. S. Tetrahedron Lett. 2011, 52, 4464.
[9] Zhuo, J. B.; Zhu, X. X.; Lin, C. X.; Bai, S.; Xie, L. L.; Yuan, Y. F. J. Organomet. Chem. 2014, 770, 85.
[10] Niu, H. T.; Yin, Z.; Su, D.; Niu, D.; He, J.; Cheng, J. P. Dalton Trans. 2008, 3694.
[11] Satheshkumar, A.; Manivannan, R.; Elango, K. P. J. Organomet. Chem. 2014, 750, 98.
[12] Klimova, T.; Klimova, E. I.; García, M. M.; Stivalet, J. M. M.; Ramírez, L. R. J. Organomet. Chem. 2001, 633, 137.
[13] Kong, D.; Weng, T.; He, W.; Liu, B.; Jin, S.; Hao, X.; Liu, S. J. Organomet. Chem. 2013, 727, 19.
[14] Thakur, A.; Mandal, D.; Sao, S.; Ghosh, S. J. Organomet. Chem. 2012, 715, 129.
[15] Thomas, J. L.; Howarth, J.; Hanlon, K.; McGuirk, D. Tetrahe-dron Lett. 2000, 41, 413.
[16] Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112.
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