A self-complexing [2]catenane

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 148-151

  Cabezon, Beatriz ^a   Cao, Jianguo ^a   Raymo, Françisco M ^a   Stoddart, J Fraser ^a   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Catenanes; Homodimeric complexes; Molecular recognition; Supramolecular chemistry

Indexed keywords

CATENANE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034598541     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<148::AID-ANIE148>3.0.CO;2-7     Document Type: Article

References (71)

1. a) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196;
2. a) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196;
3. b) M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401;
4. c) M. C. T. Fyfe, J. F. Stoddart, Adv. Supramol. Chem. 1999, 5, 1-53.
5. a) G. von Kiedrowski, Bioorg. Chem. Front. 1993, 3, 113-146;
6. b) J. Rebek, Jr., Angew. Chem. 1990, 102, 261-272; Angew. Chem. Int. Ed. Engl. 1990, 29, 245-255;
7. b) J. Rebek, Jr., Angew. Chem. 1990, 102, 261-272; Angew. Chem. Int. Ed. Engl. 1990, 29, 245-255;
8. c) S. Hoffmann. Angew. Chem. 1992, 104, 1032-1035; Angew. Chem. Int. Ed. Engl. 1992, 31, 1013-1016;
9. c) S. Hoffmann. Angew. Chem. 1992, 104, 1032-1035; Angew. Chem. Int. Ed. Engl. 1992, 31, 1013-1016;
10. d) L. E. Orgel, Nature 1992, 358, 203-209;
11. e) E. A. Winter, M. M. Conn, J. Rebek, Jr., Acc. Chem. Res. 1994, 27, 108-203;
12. f) L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118;
13. g) S. Kauffman, Nature 1996, 382, 496-497;
14. h) D. H. Lee, K. Severin, M. R. Ghadiri, Curr. Opin. Chem. Biol. 1997, 1, 491-496;
15. i) A. Luther, R. Brandsch, G. von Kiedrowski, Nature 1998, 396, 245-248.
16. a) J. L. Atwood, K. T. Holman, J. W. Steed, Chem. Commun. 1996, 1401-1407;
17. b) L. R. MacGillivray, J. L. Atwood, Nature 1997 389, 469-472;
18. c) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
19. d) R. G. Chapman, J. C. Sherman, Tetrahedron 1997, 53, 15 911-15 945;
20. e) L. J. Barbour, G. W. Orr, J. L. Alwood, Nature 1998, 393, 671-673;
21. f) J. Rebek, Jr., Acc. Chem. Res. 1999, 32, 278-286;
22. g) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931-967.
23. a) P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 1294-1297;
24. a) P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 1294-1297;
25. b) P. R. Ashton, I. W. Parsons, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, R. Wolf, Angew. Chem. 1998, 110, 2016-2019; Angew. Chem. Int. Ed. 1998, 37, 1913-1916;
26. b) P. R. Ashton, I. W. Parsons, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, R. Wolf, Angew. Chem. 1998, 110, 2016-2019; Angew. Chem. Int. Ed. 1998, 37, 1913-1916;
27. c) N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520; Angew. Chem. Int. Ed. 1998, 37, 2361-2364;
28. c) N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520; Angew. Chem. Int. Ed. 1998, 37, 2361-2364;
29. d) N. Yamaguchi, H. W. Gibson, Angew. Chem. 1999, 111, 195-199; Angew. Chem. Int. Ed. 1999, 38, 143-147.
30. d) N. Yamaguchi, H. W. Gibson, Angew. Chem. 1999, 111, 195-199; Angew. Chem. Int. Ed. 1999, 38, 143-147.
31. a) K. Hirotsu, T. Higuchi, K. Fujita, T. Ueda, A. Shinoda, T. Imoto, I. Tahushi, J. Org. Chem. 1982, 47, 1143-1144;
32. b) J. L. Sessler, A. Andrievsky, P. A. Gale, V. Lynch, Angew. Chem. 1996, 108, 2954-2957; Angew. Chem. Int. Ed. Engl. 1996, 35, 2782-2785;
33. b) J. L. Sessler, A. Andrievsky, P. A. Gale, V. Lynch, Angew. Chem. 1996, 108, 2954-2957; Angew. Chem. Int. Ed. Engl. 1996, 35, 2782-2785;
34. c) A. Zanotti-Gerosa, E. Solari, L. Giannini, A. Chiesa-Villa, C. Rizzoli, Chem. Commun. 1996, 119-120;
35. d) M. Dimitrius, A. Terzius, A. W. Coleman, C. de Rango, Carhohydr. Res. 1996, 282, 125-135;
36. e) I. Baxter, A. Ben-Haida, H. M. Colquhoun, P. Hodge, F. H. Kohnke, D. J. Williams, Chem. Commun. 1998, 2213-2214.
37. For books and reviews on molecules incorporating interlocked components, see a) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162;
38. b) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945;
39. c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828;
40. d) M. Belohradsky, F. M. Raymo, J. F. Stoddart, Collect. Czech. Chem. Commun. 1996, 61, 1-43;
41. e) M. Belohradsky, F. M. Raymo, J. F. Stoddart, Collect. Czech. Chem. Commun. 1996, 61, 527-557;
42. f) M. Fujita, K. Ogura, Coord. Chem. Rev. 1996, 148, 249-264;
43. g) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 986-988; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944;
44. g) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 986-988; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944;
45. h) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976;
46. i) M. Fujita, Acc. Chem. Res. 1999, 32, 53-61;
47. j) D. A. Leigh, A. Murphy, Chem. Int. 1999, 178-183;
48. k) G. A. Breault, C. A. Hunter, P. C. Mayers, Tetrahedron 1999, 55, 5265-5293;
49. l) Molecular Catenanes, Rotaxanes and Knots (Eds.: C. O. Dietrich-Buchecker, J.-P. Sauvage), Wiley-VCH, Weinheim, 1999;
50. m) F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1664.
51. a) D. B. Amabilino, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, J. Y. Lee, S. Menzer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 4295-4307;
52. b) D. B. Amabilino, P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 1295-1302.
53. a) P. R. Ashton, S. Menzer, F. M. Raymo, G. K. H. Shimizu, J. F. Stoddart, D. J. Williams, Chem. Commun. 1996, 487-490;
54. b) M. Asakawa, P. R. Ashton, S. Menzer, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 877-893.
55. 6 was prepared by treating the dibromide 2 with 4,4′-bipyridine. The dibromide 2 was synthesized in three steps by 1) allowing methyl 4-hydroxybenzoate to react with 2,6-bis(hydroxymethyl)pyridine ditosylate (tosylate = toluene-4-sulfonate),2) reducing the ester groups, and 3) brominating the resulting hydroxymethyl groups.
56. o|), 2θ ≤ 120) and 1507 parameters. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-132674. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
57. The mean interplanar separations between the inside and alongside 1,5-dioxynaphthalene ring systems and the inside hipyridinium unit are 3.37 and 3.32 Å, respectively.
58. The C⋯O and H⋯O distances and the C-H⋯O angles are 3.29 Å, 2.38 Å, 158 and 3.30 Å, 2.44 Å, 148, respectively.
59. The mean interplanar separations between the interacting 1,5-dioxynaphthalene and bipyridinium units and between the phenoxy and pyridyl rings are 3.42 and 3.67 Å, respectively.
60. The H⋯π distance and the C-H⋯π angle are 2.95 Å and 139.
61. The H⋯π distance and the C-H⋯π angle are 2.77 Å and 132. C-H⋯π interactions of this type have been observed previously; see, for example, a) M. Asakawa, P. R. Ashton, W. Hayes, H. M. Janssen, E. W. Meijer, S. Menzer, D. Pasini, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 920-931;
62. b) P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Pérez-García, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587-602.
63. I. O. Sutherland, Annu. Rep. NMR Spectrosc. 1971, 4, 71-235.
64. K. A. Connors, Binding Constants, Wiley, New York, 1987.
65. a) J. P. Waltho, D. H. Williams, J. Am. Chem. Soc. 1989, 111, 2475-2480;
66. b) M. Schäfer, T. R. Schneider, G. M. Sheldrick, Structure 1996, 4, 1509-1515;
67. c) P. J. Loll, A. E. Bevivino, B. D. Korty, P. H. Axelsen, J. Am. Chem. Soc. 1997, 119, 1516-1522;
68. d) G. M. Sheldrick, E. Paulus, L. Vértesy, F. Hahn, Acta Crystallogr. Sect. B 1995, 51, 89-98;
69. e) M. Schäfer, E. Pohl, K. Schimdt-Bäse, G. M. Sheldrick, R. Hermann, A. Malabarba, M. Nebuloni, G. Pelizzi. Helv. Chim. Acta 1996, 79, 1916-1924;
70. f) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193.
71. f) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193.