Functionalized [2]rotaxanes

Israel Journal of Chemistry

Volumn 36, Issue 4, 1996, Pages 329-340

  Asakawa, Masumi ^a   Ashton, Peter R ^a   Iqbal, Sayeedha ^a   Quick, Andrew ^b   Stoddart, J Fraser ^a   Tinker, Nigel D ^c   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c SELLAFIELD LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030335267     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijch.199600047     Document Type: Article

References (64)

1. (a) Haddon, R.C.; Lamola, A.A. Proc. Natl. Acad. Sci. U.S.A. 1985, 85, 1874.
2. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 28, 29.
3. (c) Miller, J.S. Adv. Mater. 1990, 2, 378.
4. (d) Lindsey, J.S. New J. Chem. 1991, 15, 153.
5. (e) Whitesides, G.M.; Mathias, J.P.; Seto, C.T. Science 1991, 254, 1312.
6. (f) Philp, D.; Stoddart, J.F. Synlett 1991, 445.
7. (g) Whitesides, G.M.; Simanek, E.E.; Mathias, J.F.; Seto, C.T.; Chin, D.N.; Mammen, M.; Gordon, D.M. Acc. Chem. Res. 1995, 28, 37.
8. (h) Amabilino, D.B.; Stoddart, J.F. Chem. Rev. 1995, 95, 2725.
9. (i) Philp, D.; Stoddart, J.F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
10. For references on catenanes, see: (a) Ashton, P.R.; Ballardini, R.; Balzani, V.; Blower, M.; Ciano, M.; Gandolfi, M.T.; McLean, C.H.; Philp, D.; Prodi, L.; Spencer, N.; Stoddart, J.F.; Tolley, M.S. New J. Chem. 1993, 17, 689.
11. (b) Amabilino, D.B.; Ashton, P.R.; Brown, C.L.; Córdova, E.; Godinez, L.A.; Goodnow, T.T.; Kaifer, A.E.; Newton, S.P.; Pietraszkiewicz, M.; Philp, D.; Raymo, F. M.; Reder, A.S.; Rutland, M.T.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Williams, D.J. J. Am. Chem. Soc. 1995, 117, 1271.
12. (c) Pérez-García, L.; Stoddart, J.F.; White, A.J.P.; Williams, D.J. Angew. Chem., Int. Ed. Engl. 1995, 34, 571.
13. (d) Dietrich-Buchecker, C.O.; Sauvage, J.-P. In Biorganic Chemistry Frontiers Vol. 2 Dugas, H., Ed.; Springer-Verlag, Weinheim, 1991; Vol. 2, p 195.
14. (d) Dietrich-Buchecker, C.O.; Sauvage, J.-P. In Biorganic Chemistry Frontiers Vol. 2 Dugas, H., Ed.; Springer-Verlag, Weinheim, 1991; Vol. 2, p 195.
15. (e) Gruter, G.J.M.; Dekanter, F.J.J.; Markies, P.R.; Nomoto, T.; Akkerman, T.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12180.
16. (f) Lu, T.B.; Zhang, L.; Gokel, G.W.; Kaifer, A.E. J. Am. Chem. Soc. 1993, 115, 2542.
17. (g) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature (London) 1994, 367, 720.
18. (h) Hoss, R.; Vögue, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375.
19. (i) Gunter, M.J.; Hockless, D.C.R.; Johnson, M.R.; Skelton, B.W.; White, A.H. J. Am. Chem. Soc. 1994, 116, 4810.
20. (j) Adams, H.; Carver, F.J.; Hunter, C.A. J. Chem. Soc., Chem. Commun. 1995, 809.
21. For references on rotaxanes, see: (a) Chambron, J.-C.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1993, 115, 6109.
22. (b) Chambron, J.C.; Heitz, V.; Sauvage, J.-P. Bull. Soc. Chim. Fr. 1995, 132, 340.
23. (c) Gibson, H.W.; Marand, H. Adv. Mater. 1993, 5, 11.
24. (d) Bissell, R.A.; Córdova, E.; Kaifer, A.E.; Stoddart, J.F. Nature (London) 1994, 369, 133.
25. (e) Gibson, H.W.; Bheda, M.C.; Engen, P.T. Prog. Polym. Sci. 1994, 19, 843.
26. (f) Benniston, A.C.; Harriman, A.; Lynch, V.M. Tetrahedron Lett. 1994, 35, 1473.
27. (g) Diederich, F.; Dietrich-Buchecker, C.O.; Nierengarten, J.F.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1995, 781.
28. (h) Sleiman, H.; Baxter, P.; Lehn, J.-M.; Rissanen, K. J. Chem. Soc., Chem. Commun. 1995, 715.
29. For references on the clipping approach to rotaxanes, see: (a) Ashton, P.R.; Grognuz, M.; Slawin, A.M.Z.; Stoddart, J.F.; Williams, D.J. Tetrahedron Lett. 1991, 32, 6235.
30. (b) Ashton, P.R.; Bissell, R.A.; Spencer, N.; Stoddart, J.F.; Tolley, M.S. Synlett 1992, 914.
31. (c) Ashton, P.R.; Bissell, R.A.; Górski, R.; Philp, D.; Spencer, N.; Stoddart, J.F.; Tolley, M.S. Synlett, 1992, 919.
32. (d) Ashton, P.R.; Bissell, R.A.; Spencer, N.; Stoddart, J.F.; Tolley, M.S. Synlett 1992, 923.
33. (e) Ashton, P.R.; Johnston, M.R.; Stoddart, J.F.; Tolley, M.S.; Wheeler, J.W. J. Chem. Soc., Chem. Commun. 1992, 128.
34. For references on the threading approach to rotaxanes, see: (a) Yamanari, K.; Shimura, Y. Bull. Chem. Soc. Jpn. 1983, 56, 2283.
35. (b) Ogino, H.; Ohata, K. Inorg. Chem. 1984, 23, 3314.
36. (c) Born, M.; Ritter, H. Makromol. Chem., Rapid Commun. 1991, 12, 471.
37. (d) Wenz, G.; Wolf, F.; Wagner, M.; Kubik, S. New J. Chem. 1993, 17, 729.
38. (e) Anelli, P.-L.; Asakawa, M.; Ashton, P.R.; Bissell, R.A.; Clavier, G.; Górski, R.; Kaifer, A.E.; Langford, S.J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Tolley, M.S.; Williams, D.J. Chem. Eur. J., in press.
39. For references on the slipping approach to rotaxanes, see: (a) Ashton, P.R.; Belohradsky, M.; Philp, D.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1993, 1269.
40. (b) Ashton, P.R.; Belohradsky, M.; Philp, D.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1993, 1274.
41. (c) Amabilino, D.B.; Ashton, P.R.; Belohradsky, M.; Raymo, F.M.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1995, 745.
42. Amabilino, D.B.; Ashton, P.R.; Belohradsky, M.; Raymo, F.M.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1995, 751.
43. (a) Davidson, R.B.; Izatt, R.M.; Christensen, J.J.; Shultz, R.A.; Dishong, D.M.; Gokel, G.W. J. Org. Chem. 1984, 49, 5080; Patai, S.; Rappaport, Z., Eds.; Crown Ethers and Analogs; John Wiley & Sons, New York, 1989.
44. (a) Davidson, R.B.; Izatt, R.M.; Christensen, J.J.; Shultz, R.A.; Dishong, D.M.; Gokel, G.W. J. Org. Chem. 1984, 49, 5080; Patai, S.; Rappaport, Z., Eds.; Crown Ethers and Analogs; John Wiley & Sons, New York, 1989.
45. (b) Inoue, Y.; Gokel, G.W., Eds.; Cation Binding by Macrocycles, Marcel Dekker Inc, New York, 1990.
46. Anelli, P.L.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M.T.; Goodnow, T.T.; Kaifer, A.E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M.V.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Vicent, C.; Williams, D.J. J. Am. Chem. Soc. 1992, 114, 193.
47. For preliminary communications of the results reported in this paper, see: (a) Ashton, P.R.; Iqbal, S.; Stoddart, J.F.; Tinker, N.D. Chem. Commun. 1996, 479.
48. (b) Asakawa, M.; Ashton, P.R.; Iqbal, S.; Stoddart, J.F.; Tinker, N.D.; White, A.J.P.; Williams, D.J. Chem. Commun. 1996, 483.
49. Hill, Z.D.; MacCarthy, P. J. Chem. Ed. 1986, 64, 162.
50. For a review of the nature of π-π interactions, see: (a) Hunter, C.A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584; For experimental approaches for studying the nature of π-π interactions, see:
51. (b) Cozzi, F.; Cinquini, M.; Annuziata, R.; Dwyer, T.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 5729.
52. (c) Cozzi, F.; Cinquini, M.; Annuziata, R.; Dwyer, T.; Siegel, J.S. J. Am. Chem. Soc. 1993, 114, 5330.
53. For a discussion of the computational approaches to studying the nature and geometry of π-π interactions, see: (d) Jorgensen, W.L.; Severance, D.L. J. Am. Chem. Soc. 1990, 112, 4768.
54. (e) Hunter, C.A.; Sanders, J.K.M. J. Am. Chem. Soc., 1990, 112, 5525.
55. For a discussion of T-type interactions, see: (a) Burley, S.K.; Petsko, G.A. Science 1985, 229, 23.
56. (b) Grossell, M.C.; Cheetham, A.K. J. Org. Chem. 1993, 58, 6654.
57. (c) Pailwal, S.; Geib, S.; Wilcox, C.S. J. Am. Chem. Soc. 1994, 116, 4497.
58. (d) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665.
59. For articles on hydrogen bonding, see: (a) Aakeröy, C.B.; Seddon, K.R. Chem. Soc. Rev. 1993, 397.
60. (b) Etter, M.C. Acc. Chem. Res. 1990, 23, 120.
61. (c) Hamilton, A.D. J. Chem. Ed. 1990, 67, 821. For articles discussing the [C-H⋯O] hydrogen bond, see:
62. (d) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
63. (e) Desiraju, D.R. Acc. Chem. Res. 1991, 24, 290; Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1993, 115, 4540.
64. (e) Desiraju, D.R. Acc. Chem. Res. 1991, 24, 290; Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1993, 115, 4540.