New Host Molecules with Imidazoliums as Functional Arms: Syntheses and Anion Recognition
Yi Yuan
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorZong-Lin Jiang
Department of Chemistry, Daxian Teacher s College, Dazhou, Sichuan 635000, China
Search for more papers by this authorGe Gao
Department of Chemistry, Daxian Teacher s College, Dazhou, Sichuan 635000, China
Search for more papers by this authorGuo-Lin Zhang
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorJing-Song You
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorRu-Gang Xie
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorYi Yuan
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorZong-Lin Jiang
Department of Chemistry, Daxian Teacher s College, Dazhou, Sichuan 635000, China
Search for more papers by this authorGe Gao
Department of Chemistry, Daxian Teacher s College, Dazhou, Sichuan 635000, China
Search for more papers by this authorGuo-Lin Zhang
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorJing-Song You
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorRu-Gang Xie
Department of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorAbstract
The bridged tri-imidazoliums 3 · 3X− — 5 · 3X− (X− = PF6−, Br−, I−) and bis-imidazoliums 6 × 2PF6− were synthesized by N-quaternization of imidazole derivative 1 in acetonitrile under reflux. UV spectroscopic titration experiments showed that the halide salts and hexafluorophosphate salts of these imidazoliums exhibited good recognition toward anions in water and in acetonitrile, respectively.
References
- 1(a)
Steed, J. W.;
Atwood, J. L.
Supramolecular Chemistry; A Concise Introduction,
John Wiley & Sons, Chichester,
2000.
(b)
Lehn, J.-M.
Supramolecular Chemistry; Concepts and Perspective,
VCH, Weinheim,
1995.
10.1002/3527607439 Google Scholar
- 2(a)
Beer, P. D.;
Gale, P. A.
Angew. Chem., Int. Ed.
2001,
40,
486.
10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar(b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609. (c) Bianchi, A.; Bowman-James, K.; García-España, E. Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997.
- 3(a) Sato, K.; Arai, S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219. (b) Elaiwi, A.; Hitchcock, P. B.; Seddon, K. R.; Srinivasan, N.; Tan, Y.; Welton, T.; Zora, J. A. J. Chem. Soc., Dalton Trans. 1995, 40, 5219. (c) Avent, A. G.; Chaloner, P. A.; Day, M. P.; Seddon, K. R.; Welton, T. J. Chem. Soc., Dalton Trans. 1994, 3405.
- 4(a) Thomas, J.-L.; Howarth, J.; Hanlon, K.; McGuirk, D. Tetrahedron Lett. 2000, 41, 413. (b) Alcalde, E.; Alvarez-Rúa, C.; Garcia-Granda, S.; Garcia-Rodriguez, E.; Mesquida, N.; Pérez-García, L. Chem. Commun. 1999, 295.
- 5(a) You, J.-S.; Yu, X.-Q.; Zhang, G.-L.; Xiang, Q.-X.; Lan, J.-B.; Xie, R.-G. Chem. Commun. 2001, 1816. (b) Yuan, Y.; Yan, J.-M.; Jiang, Z.-L.; Gao, G.; Chan, A. S. C.; Xie, R.-G. Synth. Commun. 2000, 30, 4555. (c) Luo, M.-M.; Xie, R.-G.; Yuan, D.-Q.; Lu, W.; Xia, P.-F.; Zhao, H.-M. Chin. J. Chem. 1999, 17, 384. (d) Liu, Z.-C.; Zhou, C.-H.; Su, X.-Y.; Xie, R.-G. Synth. Commun. 1999, 29, 1919. (e) Zhou, C.-H.; Gu, X.-R.; Xie, R.-G.; Cai, M.-S. Synth. Commun. 1999, 29, 1217. (f) Liu, Z.-C.; Zhou, C.-H.; Xie, R.-G. Chin. Chem. Lett. 1997, 8, 387. (g) Zhou, C.-H.; Xie, R.-G.; Zhao, H.-M. Org. Prep. Proeed. Int. 1996, 28, 345. (h) Luo, M.-M.; Guo, S.-J.; Zhou, C.-H.; Xie, R.-G. Heterocycles 1995, 41, 1421.
- 6 Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry, John Wiley & Sons, Chichester, 1999.
- 7(a) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. (b) Watanabe, S.; Onogawa, O.; Komatsu, Y.; Yoshida, K. J. Am. Chem. Soc. 1998, 120, 229. (c) Liu, Y.; Li, B.; Han, B.-H.; Li, Y.-M.; Chen, R.-T. J. Chem. Soc., Perkin Trans. 2 1997, 1275. (d) Liu, Y.; Zhang, Y.-M.; Sun, S.-X.; Li, Y.-M.; Chen, R.-T. J. Chem. Soc., Perkin Trans. 2 1997, 1609. (e) Asakawa, M.; Brown, C. L.; Pasini, D.; Stoddart, J. F.; Wyatt, P. G. J. Org. Chem. 1996, 61, 7234. (f) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.-Y.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950.
- 8(a) Polster, J.; Lachmann, H. Spectrometric Titrations, VCH, Weibheim, 1989. (b) Connors, K. A. Binding Constants. the Measurement of Molecular Complex, John Wiley & Sons, New York, 1987. (c) Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
- 9 Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6392.
