Reviews

Supramolecular Catenane Chemistry Based on Crown Ether Derivatives

  • Shen Jianfeng ,
  • Yu Xuetao ,
  • Ye Yuyuan ,
  • Chen Rener ,
  • Jiang Huajiang ,
  • Zhou Qizhong
Expand
  • Department of Chemistry, Taizhou University, Taizhou 317000

Received date: 2012-06-05

  Revised date: 2012-07-04

  Online published: 2012-07-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172166) and the Natural Science Foundation of Zhejiang Province (No. Y4100783).

Abstract

Catenanes, as one kind of the basic mechanically interlocked superstructures, have drawn considerable attention from the scientific community, not only because of their topological importance and unique properties, but also due to their potential for applications in artificial molecular machines and functional nanomaterials. Template-directed protocols have facilitated the efficient preparations of various kinds of catenanes. Thereinto, as the first macrocyclic host, crown ether derivatives have been widely used to prepare catenanes. Therefore, the development of supramolecular catenane chemistry based on crown ether derivatives is systematically addressed.

Cite this article

Shen Jianfeng , Yu Xuetao , Ye Yuyuan , Chen Rener , Jiang Huajiang , Zhou Qizhong . Supramolecular Catenane Chemistry Based on Crown Ether Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2265 -2275 . DOI: 10.6023/cjoc201206004

References

[1] Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959.

[2] Beves, J. E. B.; Blight, A.; Campbell, C. J.; Leigh, D. A.; Mcburney, R. T. Angew. Chem., Int. Ed. 2011, 50, 9260.

[3] Forgan, R. S.; Sauvage, J.-P.; Stoddart, J. F. Chem. Rev. 2011, 111, 5434.

[4] Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643.

[5] Niu, Z.; Gibson, H. W. Chem. Rev. 2009, 109, 6024.

[6] Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.

[7] Safarowsky, O.; Windisch, B.; Mohry, A.; Vögtle, F. J. Prakt. Chem. 2000, 342, 437.

[8] Hudson, B.; Vinograd, J. Nature 1967, 216, 647.

[9] Clayton, D. A.; Vinograd, J. Nature 1967, 216, 652.

[10] Wikoff, W. R.; Liljas, L.; Duda, R. L.; Tsuruta, H.; Hendrix, R. W.; Johnson, J. E. Science 2000, 289, 2129.

[11] Logeman, E.; Rissler, K.; Schill, G.; Fritz, H. Ber. Dtsch. Chem. Ges. 1981, 114, 2245.

[12] Schill, G.; Rissler, K.; Fritz, H.; Vetter, W. Angew. Chem., Int. Ed. 1981, 20, 187.

[13] Schill, G.; Schweickert, N.; Fritz, H.; Vetter, W. Angew. Chem., Int. Ed. 1983, 22, 889.

[14] Sauvage, J.-P.; Collin, J.-P.; Chambron, J.-C.; Gulllerez, S.; Coudret, C. Chem. Rev. 1994, 94, 993.

[15] Stoddart, J. F. Chem. Soc. Rev. 2009, 38, 1521.

[16] Beves, J. E.; Blight, B. A.; Campbell, C. J.; Leigh, D. A.; McBurney, R. T. Angew. Chem., Int. Ed. 2011, 50, 9260.

[17] Leigh, D. A.; Lusby, P. J.; Teat, S. J.; Wilson, A. J.; Wong. J. K. Y. Angew. Chem., Int. Ed. 2001, 40, 1538.

[18] Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R. J. Am. Chem. Soc. 2004, 126, 15364.

[19] Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303.

[20] Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. 1992, 31, 1619.

[21] Johnston, A. G.; Leigh, D. A.; Pritchard, R. J. Angew. Chem., Int. Ed. 1995, 34, 1209.

[22] Harada, A. Acc. Chem. Res. 2001, 34, 456.

[23] Liu, Y.; Yang, Z.; Chen, Y. J. Org. Chem. 2008, 73, 5298.

[24] Kim, K. Chem. Soc. Rev. 2002, 31, 96.

[25] Park, K.-M.; Kim, S.-Y.; Heo, J.; Whang, D.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2002, 124, 2140.

[26] Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. 1989, 28, 1396.

[27] Balzani, V.; Credi, A.; Langford, S. J.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 2000, 122, 3542.

[28] Amabilino, D. B.; Ashton, P. R.; Brown, C. L.; Cordora, E.; Godinez, L. A.; Godinez, L. A.; Kaifer, A. E.; Newton, S. P.; Pietraszkiewicz, M.; Philp, D.; Raymo, F. M.; Reder, A. S.; Rutland, M. T.; Slawin, A. M. E.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 1271.

[29] Yan, X.; Wei, P.; Zhang, M.; Chi, X.; Liu, J.; Huang, F. Org. Lett. 2011, 13, 6370.

[30] Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042.

[31] Guidry, E. N.; Cantrill, S. J.; Stoddart. J. F.; Grubbs, R. H. Org. Lett. 2005, 7, 2129.

[32] Chiu, S.-H.; Elizarov, A. M.; Glink, P. T.; Stoddart, J. F. Org. Lett. 2002, 4, 3561.

[33] Loeb, S. J.; Wisner, J. A. Angew. Chem., Int. Ed. 1998, 37, 2838.

[34] Loeb, S. J. Chem. Soc. Rev. 2007, 36, 226.

[35] Hubbard, A. L.; Dacidson, G. J. E.; Patel, R. H.; Wisner, J. A.; Loeb. S. J. Chem. Commun. 2004, 138.

[36] Zhu, X.-Z.; Chen, C.-F. J. Am. Chem. Soc. 2005, 127, 13158.

[37] Blanco, V.; Chas, M.; Abella, D.; Peinador, C.; Quintela, J. M. J. Am. Chem. Soc. 2007, 129, 13978.

[38] Zhang, M.; Luo, Y.; Zheng, B.; Yan, X.; Fronczek, F. R.; Huang, F. Eur. J. Org. Chem. 2010, 6798.

[39] Miljani?, O. Š.; Stoddart, J. F. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 12966.

[40] Liu, Y.; Bruneau, A.; He, J.; Abliz, Z. Org. Lett. 2008, 10, 765.

[41] Niu, Z.; Slebodnick, C.; Bonrad, K.; Huang, F.; Gibson, H. W. Org. Lett. 2011, 13, 2872.

[42] Yan, X.; Wei, P.; Xia, B.; Huang, F.; Zhou, Q. Chem. Commun. 2012, 48, 4968.

[43] Zhang, M.; Zhu, K.; Huang, F. Chem. Commun. 2010, 46, 8131.

[44] Niu, Z.; Huang, F.; Gibson, H. W. J. Am. Chem. Soc. 2011, 133, 2836.

[45] Liu, M.; Li, S.; Zhang, M.; Zhou, Q.; Wang, F.; Hu, M.; Fronczek, F. R.; Li, N.; Huang, F. Org. Biomol. Chem. 2009, 7, 1288.

[46] Li, S.; Liu, M.; Zheng, B.; Zhu, K.; Wang, F.; Li, N.; Zhao, X.-L.; Huang, F. Org. Lett. 2009, 11, 3350.

[47] Liu, M.; Li, S.; Hu, M.; Wang, F.; Huang, F. Org. Lett. 2010, 12, 760.

[48] Fang, L.; Wang, C.; Fahrenbach, A. C.; Trabolsi, A.; Botros, Y. Y.; Stoddart, J. F. Angew. Chem., Int. Ed. 2011, 50, 1805.

[49] Peinador, C.; Blanco, V.; Quintela, J. M. J. Am. Chem. Soc. 2009, 131, 920.

[50] Vickers, M. S.; Beer, P. D. Chem. Soc. Rev. 2007, 36, 211. Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. 1994. 33. 1286.

Outlines

/