Self-assembly of [2]catenanes containing metals in their backbones

Accounts of Chemical Research

Volumn 32, Issue 1, 1999, Pages 53-61

  Fujita, Makoto ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032909480     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9701068     Document Type: Article

References (60)

1. van Gulick, N. New J. Chem. 1993, 17, 619. A preprint of this paper was first available in 1960.
2. Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789.
3. (a) Schill, G. Catenanes, Rotaxane, and Knots; Academic Press: New York, 1971.
4. (b) Sauvage, J.-P.; Dietrich-Buchecker, C. O. Molecular Topology: Catenanes, Rotaxanes, and Knots; VCH and Wiley: New York, in press.
5. Wasserman, E. J. Am. Chem. Soc. 1960, 82, 4433.
6. (a) Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kintzinger, J. P. Tetrahedron Lett. 1983, 24, 5095.
7. (b) Dietrich-Buchecker C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795.
8. (c) Sauvage, J.-P. Acc. Chem. Res. 1990, 23, 319.
9. (d) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J.-C. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, 1995; Vol. 9, Chapter 2.
10. (e) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
11. (a) Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; William, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396.
12. (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
13. (b) Stoddart, J. F.; Raymo, F.; Amabilino, D. B. In Comprehensive Supramolecular Chemistry, Lehn, J.-M., Ed.; Pergamon Press: Oxford, 1995; Vol. 9, Chapter 3.
14. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
15. (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303.
16. (b) Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809.
17. (a) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619.
18. (b) Ottens-Hildebrandt, S.; Nieger, M.; Rissanen; K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1995, 809.
19. (c) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451.
20. (a) Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209.
21. (b) Johnston, A. G.; Leigh, D. A.; Nezhat, L.; Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212.
22. (a) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810.
23. (b) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582.
24. (c) Mingos, D. M. P.; Yau, J.; Menzer, S.; D. J.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
25. Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179.
26. Fujita, M.; Ibukuro, F.; Hagihara; H.; Ogura, K. Nature 1994, 367, 720.
27. (a) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1995, 148, 249.
28. (b) Fujita, M.; Ogura, K. Bull. Chem. Soc. Jpn. 1996, 69, 1471.
29. (c) Fujita, M.; Ogura, K. J. Synth. Org. Chem. Jpn. 1994, 52, 839.
30. Fujita, M.; Ogura, K. Supramol. Sci. 1996, 3, 37.
31. (a) Seeman, N. C. Acc. Chem. Res. 1997, 30, 357.
32. (b) Du, S. M.; Seeman, N. C. J. Am. Chem. Soc. 1992, 114, 9652.
33. (c) Du, S. M.; Tse-Dinh, Y.-C.; Seeman, N. C. Biochemistry 1995, 34, 673.
34. (d) Du, S. M.; Stollar, B. D.; Seeman, N. C. J. Am. Chem. Soc. 1995, 117, 1194.
35. Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 4175.
36. Fujita, M.; Aoyagi, M.; Ibukuro, F.; Ogura, K.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 611.
37. ESI-MS is effective for the analysis of transition metal complexes. (a) Bitsch, F.; Dietrich-Buchecker, C. O.; Khémiss, A.-K.; Sauvage, J.-P.; Van Dorsselaer, A. J. Am. Chem. Soc. 1991, 113, 4023.
38. (b) Leize, E.; Van Dorsselaer, A.; Krämer, R.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 990.
39. The bridging ligand used to construct catenane 8 or its constitutive ring 6 is asymmetric since a methylene group is inserted between one 4-pyridyl nucleus and the 1,4-phenylene fragment. This provides a direction to the ligand and consequently to ring 6. Catenane 8 thus consists of two oriented interlocking rings, which is a necessary requirement for a [2]catenane to be topologically chiral. Preparation of a topologically chiral catenane: Mitchell, D. K.; Sauvage, J.-P. Angew. Chem., Int. Ed. Engl. 1988, 27, 930.
40. Fujita, M.; Ibukuro, F.; Aoyagi, M.; Mizota, T.; Yamashita, Y.; Ogura, K.; Yamaguchi, K. To be published.
41. Multicomponent self-assembly: (a) Baxter, P. N.; Lehn, J.-M.; DeCian, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 69.
42. (b) Baxter, P. N.; Lehn, J.-M.; Kneisel, B. O.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1978.
43. Molecular recognition ability of 21 for π-electronrich aromatic compounds: Fujita, M.; Nagao, S.; Iida, M.; Ogata, K.; Ogura, K. J. Am. Chem. Soc. 1993, 115, 1574.
44. Edge-to-face interaction between aromatic rings: (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23.
45. (b) Singh, J.; Thornton, J. M. FEBS Lett. 1985, 191, 1.
46. (c) Burley, S. K.; Petsko, G. A. ibid. 1986, 108, 7995 and references therein.
47. (d) Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1070.
48. Fujita, M.; Ibukuro, F.; Seki, H.; Kamo, O.; Imanari, M.; Ogura, K. J. Am. Chem. Soc. 1996, 118, 899.
49. The first synthesis of a molecular Möbius strip: (a) Walba, D. M.; Richards, R. M.; Haltiwanger, R. C. J. Am. Chem. Soc. 1982, 104, 3219.
50. (b) Walba, D. M.; Homan, T. C.; Richards, R. M.; Haltiwanger, R. C. New J. Chem. 1993, 17, 661.
51. (a) Livoreil, A.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 9399.
52. (b) Cárdenas, D. J.; Livoreil, A.; Sauvage, J.-P. J. Am. Chem. Soc. 1996, 118, 11980.
53. (a) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133.
54. (b) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montalti, M. Shipway, A. N.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Venturi, M.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 333.
55. Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley and Sons: New York, 1997; pp 155-189.
56. Multiring catenanes: (a) Bitsch, F.; Dietrich-Buchecker, C. O.; Khemiss, A. K.; J.-P. Sauvage, van Dorsselear, A. J. Am. Chem. Soc. 1991, 113, 4023.
57. (b) Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1286.
58. (c) Whang, D.; Park, K.-M., Heo, J.; Ashton, P., Kim, K. J. Am. Chem. Soc. 1998, 120, 4899.
59. Recent progress in catenane synthesis: (a) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608.
60. Drexler, K. E. Nanosystems, Molecular machinery, manufacturing and computation; Wiley: New York, 1992.