Binding modes of cucurbit[6]uril and cucurbit[7]uril with a series of bis-pyridinium compounds

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 76, Issue 3-4, 2013, Pages 333-344

  He, Suhang ^a   Zhou, Chan ^a   Zhang, Haibo ^a   Zhou, Xiaohai ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Binding behavior; Cucurbit n uril; Host guest system; Pseudorotaxane; Supramolecular chemistry

Indexed keywords

EID: 84880132823     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0204-y     Document Type: Article

References (38)

1. Freeman, W.A., Mock, W.L., Shih, N.-Y.: Cucurbituril. J. Am. Chem. Soc. 103, 7367-7368 (1981)
2. Kim, J., Jung, I.S., Kim, S.Y., Lee, E., Kang, J.K., Sakamoto, S., Yamaguchi, K., Kim, K.: New cucurbituril homologues: syntheses, isolation, characterization, and x-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 122, 540-541 (2000)
3. Mock, W.L., Shih, N.-Y.: Host-guest binding capacity of cucurbituril. J. Org. Chem. 48, 3618-3619 (1983)
4. Mock, W.L., Shih, N.-Y.: Structure and selectivity in host-guest complexes of cucurbituril. J. Org. Chem. 51, 4440-4446 (1986)
5. Mock, W.L., Shih, N.-Y.: Organic ligand-receptor interactions between cucurbituril and alkylammonium ions. J. Am. Chem. Soc. 110, 4706-4710 (1988)
6. Mock, W.L., Shih, N.-Y.: Dynamics of molecular recognition involving cucurbituril. J. Am. Chem. Soc. 111, 2697-2699 (1989)
7. Buschmann, H.-J., Cleve, E., Schollmeyer, E.: Cucurbituril as a ligand for the complexation of cations in aqueous solutions. Inorg. Chem. Acta 193, 93-97 (1992)
8. Meschke, C., Buschmann, H.-J., Schollmeyer, E.: Complexes of cucurbituril with alkyl mono- and diammonium ions in aqueous formic acid studied by calorimetric titrations. Thermochim. Acta 297, 43-48 (1997)
9. Buschmann, H.-J., Schollmeyer, E.: Cucurbituril and β-cyclodextrin as hosts for the complexation of organic dyes. J. Incl. Phenom. Macrocycl. Chem. 29, 167-174 (1997)
10. Buschmann, H.-J., Jansen, K., Schollmeyer, E.: The formation of cucurbituril complexes with amino acids and amino alcohols in aqueous formic acid studied by calorimetric titrations. Thermochim. Acta 317, 95-98 (1998)
11. Buschmann, H.-J., Jansen, K., Schollmeyer, E.: Cucurbituril as host molecule for the complexation of aliphatic alcohols, acids and nitriles in aqueous solution. Themochim. Acta. 346, 33-36 (2000)
12. Buschmann, H.-J., Cleve, E., Jansen, K., Schollmeyer, E.: Determination of complex stabilities with nearly insoluble host molecules: cucurbit[5]uril, decamethylcucurbit[5]uril and cucurbit[6]uril as ligands for the complexation of some multicharged cations in aqueous solution. Anal. Chim. Acta 437, 157-163 (2001)
13. Buschmann, H.-J., Jansen, K., Schollmeyer, E.: Cucurbit[6]uril as ligand for the complexation of lanthanide cations in aqueous solution. Inorg. Chem. Commun. 6, 531-534 (2003)
14. Lee, E., Heo, J., Kim, K.: A three-dimensional polyrotaxane network. Angew. Chem. Int. Ed. 39, 2699-2701 (2000)
15. Whang, D., Heo, J., Kim, C.A., Kim, K.: Helical polyrotaxane: cucurbituril 'beads' threaded onto a helical one-dimensional coordination polymer. Chem. Commun. 24, 2361-2362 (1997)
16. Lee, E., Kim, J., Heo, J., Whang, D., Kim, K.: A two-dimensional polyrotaxane with large cavities and channels: a novel approach to metal-organic open-frameworks by using supramolecular building blocks. Angew. Chem. Int. Ed. 40, 399-402 (2001)
17. Whang, D., Kim, K.: Polycatenated two-dimensional polyrotaxane net. J. Am. Chem. Soc. 119, 451-452 (1997)
18. Wagner, B.D., MacRae, A.I.: The lattice inclusion compound of 1,8-ans and cucurbituril: a unique fluorescent solid. J. Phys. Chem. B 103, 10114-10119 (1999)
19. Wagner, B.D., Fitzpatrick, S.J., Gill, M.A., MacRae, A.I., Stojanovic, N.: A fluorescent host-guest complex of cucurbituril in solution: a molecular Jack O'Lantern. Can. J. Chem. 79, 1101-1104 (2001)
20. Marquez, C., Hudgins, R.R., Nau, W.M.: Mechanism of host-guest complexation by cucurbituril. J. Am. Chem. Soc. 126, 5806-5816 (2004)
21. Day, A.I., Arnold, A.P., Blanch, R.J., Snushall, B.: Controlling factors in the synthesis of cucurbituril and its homologues. J. Org. Chem. 66, 8094-8100 (2001)
22. Whang, D., Park, K.M., Heo, J., Ashton, P., Kim, K.: Molecular necklace: quantitative self-assembly of a cyclic oligorotaxane from nine molecules. J. Am. Chem. Soc. 120, 4899-4900 (1998)
23. Roh, S.G., Park, K.M., Park, G.J., Sakamoto, S., Yamaguchi, K., Kim, K.: Synthesis of a five-membered molecular necklace: a 2 + 2 approach. Angew. Chem. Int. Ed. 38, 637-641 (1999)
24. Park, K.M., Kim, S.Y., Heo, J., Whang, D., Sakamoto, S., Yamaguchi, K., Kim, K.: Designed self-assembly of molecular necklaces. J. Am. Chem. Soc. 124, 2140-2147 (2002)
25. Whang, D., Jeon, Y.M., Heo, J., Kim, K.: Self-assembly of a polyrotaxane containing a cyclic "bead" in every structural unit in the solid state: cucurbituril molecules threaded on a one-dimensional coordination polymer. J. Am. Chem. Soc. 118, 11333-11334 (1996)
26. Lee, J.W., Ko, Y.H., Park, S.H., Yamaguchi, K., Kim, K.: Novel pseudorotaxane-terminated dendrimers: supramolecular modification of dendrimer periphery. Angew. Chem. Int. Ed. 40, 746-749 (2001)
27. Park, K.M., Whang, D., Lee, E., Heo, J., Kim, K.: Transition metal ion directed supramolecular assembly of one- and two-dimensional polyrotaxanes incorporating cucurbituril. Chem. Eur. J. 8, 498-508 (2002)
28. Zhang, F., Yajima, T., Li, Y.Z., Xu, G.Z., Chen, H.L., Liu, Q.T., Yamauchi, O.: Iodine-assisted assembly of helical coordination polymers of cucurbituril and asymmetric copper(ii) complexes. Angew. Chem. Int. Ed. 44, 3402-3407 (2005)
29. Rekharsky, M.V., Yamamura, H., Kawai, M., Osaka, I., Arakawa, R., Sato, A., Ko, Y.H., Selvapalam, N., Kim, K., Inoue, Y.: Sequential formation of a ternary complex among dihexylammonium, cucurbit[6]uril, and cyclodextrin with positive cooperativity. Org. Lett. 8, 815-818 (2006)
30. Liu, Y., Li, X.Y., Zhang, H.Y., Li, C.J., Ding, F.: Cyclodextrin-driven movement of cucurbit[7]uril. J. Org. Chem. 72, 3640-3645 (2007)
31. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., Isaacs, L.: The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844-4870 (2005)
32. Belda, O., Moberg, C.: Bispyridylamides-coordination chemistry and applications in catalytic reactions. Coordin. Chem. Rev. 249, 727-740 (2005)
33. Ong, W., Kaifer, A.E.: Cucurbit[7]uril: A very effective host for viologens and their cation radicals. Org. Lett. 4, 1791-1794 (2002)
34. Kim, H.-J., Jeon, W.S., Ko, Y.H., Kim, K.: Supramolecular chemistry and self-assembly special feature: inclusion of methylviologen in cucurbit[7]uril. Proc. Natl. Acad. Sci. USA 99, 5007-5011 (2002)
35. Day, A.I., Arnold, A.P., Blanch, R.J., Snushall, B.: Controlling factors in the synthesis of cucurbituril and its homologues. J. Org. Chem. 66, 8094-8100 (2001)
36. Fujimoto, K., Morisaki, D., Yoshida, M., Namba, T., Hye-Sook, K., Wataya, Y., Kourai, H., Kakuta, H., Sasaki, K.: Antimalarial effect of bis-pyridinium salts, n, n′-hexamethylenebis(4-carbamoyl-1-alkylpyridinium bromide). Bioorg. Med. Chem. Lett. 16, 2758-2760 (2006)
37. Yoshida, M., Maeda, T., Okazaki, K., Nagamune, H., Kunikata, K., Tsuchiya, H., Tetsuto, N., Hiroki, K.: Synthesis and antimicrobial characteristics of n, n′-hexamethylenebis (4-carbamoyl-1-decylpyridinium bromide). Biocontrol Sci. 5, 65-71 (2000)
38. Nau, W.M., Florea, M., Assaf, K.I.: Deep inside cucurbiturils: physical properties and volumes of their inner cavity determine the hydrophobic driving force for host-guest. Isr. J. Chem. 51, 559-577 (2011)