Molecular Meccano, 56. - Anthracene-containing [2]rotaxanes: Synthesis, spectroscopic, and electrochemical properties

European Journal of Organic Chemistry

Volumn , Issue 4, 2000, Pages 591-602

  Ballardini, Roberto ^a   Balzani, Vincenzo ^b   Dehaen, Wim ^c   Dell'Erba, Adele E ^b   Raymo, Françisco M ^d   Stoddart, J Fraser ^d   Venturi, Margherita ^b  

^a Istituto di Fotochimica e Radiazioni d'Alta Energia   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cyclophanes; Molecular recognition; Molecular shuttles; Rotaxanes; Template directed synthesis

Indexed keywords

2,6 BIS[2 [2 [2 [2 [4 [2 [2 [2 [2 (4 TRIPHENYLMETHYLPHENOXY)ETHOXY]ETHOXY]ETHOXY]ETHOXY]PHENOXY]ETHOXY]ETHOXY]ETHOXY] ETHOXY]ANTHRACENE; 9,10 BIS[2 [2 [2 [2 [4 [2 [2 [2 [2 (4 TRIPHENYLMETHYLPHENOXY)ETHOXY]ETHOXY]ETHOXY]ETHOXY]PHENOXY]ETHOXY]ETHOXY]ETHOXY] ETHOXY]ANTHRACENE; ANTHRACENE DERIVATIVE; CYCLOPHANE; ROTAXANE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ENERGY TRANSFER; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034093292     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200002)2000:4<591::AID-EJOC591>3.0.CO;2-I     Document Type: Article

References (70)

1. For books and reviews on catenanes and rotaxanes, see: [1a] J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162.
2. [1b] H. W. Gibson, H. Marand, Adv. Mater. 1993, 5, 11-21.
3. [1c] H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
4. [1d] D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
5. [1e] M. Belohradsky, F. M. Raymo, J. F. Stoddart, Collect. Czech. Chem. Commun. 1996, 61, 1-43 and 527-557.
6. [1f] M. Fujita, K. Ogura, Coord. Chem. Rev. 1996, 148, 249-264.
7. [1g] R. Jäger, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.
8. [1h] S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976.
9. [1i] M. Fujita, Acc. Chem. Res. 1999, 32, 53-61.
10. [1j] D. A. Leigh, A. Murphy, Chem. Ind. 1999, 178-183.
11. [1k] G. A. Breault, C. A. Hunter, P. C. Mayers, Tetrahedron 1999, 55, 5265-5293.
12. [1l] Molecular Catenanes, Rotaxanes and Knots (Eds.: C. O. Dietrich-Buckecher, J.-P. Sauvage), VCH-Wiley, Weinheim, 1999.
13. [1m] F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1664.
14. For a definition of a "molecular shuttle", see: P.-L. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131-5133.
15. For examples of switchable rotaxanes, see: [3a] R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137.
16. [3b] M.-V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. Inf. Ed. Engl. 1997, 36, 1904-1907.
17. [3c] P. R. Ashton, R. Ballardini, V. Balzani, M. Gómez-López, S. E. Lawrence, M.-V. Martínez-Díaz, M. Montalti, A. Piersanti, L. Prodi, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 10641-10651.
18. [3d] V. Balzani, M. Gópez-López, J. F. Stoddart, Acc. Chem. Res. 1998, 31, 405-414.
19. [3e] P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Gómez-López, M. V. Martínez-Díaz, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942.
20. [3f] J.-P. Collin, P. Gaviña, J.-P. Sauvage, New J. Chem. 1997, 21, 525-528.
21. [3g] J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366.
22. [3h] J.-P. Sauvage, Acc. Chem. Res. 1998. 31, 611-619.
23. [3i] J.-P. Collin, P. Gaviña, V. Heitz, J.-P. Sauvage, Eur. J. Inorg. Chem. 1998, 1-14.
24. [3j] N. Armaroli, V. Balzani, J.-P. Collin, P. Gaviña, J.-P. Sauvage, B. Ventura, J. Am. Chem. Soc. 1999, 121, 4397-4408.
25. [3k] H. Murakami, A. Kawabuchi, K. Kotoo, M. Kunitake, N. Nakashima, J. Am. Chem. Soc. 1997, 119, 7605-7606.
26. For accounts and reviews on catenanes and rotaxanes having intercomponent [C-H⋯O] hydrogen bonds, [π⋯π] stacking, and [C-H⋯π] interactions, see: [4a] D. Pasini, F. M. Raymo, J. F. Stoddart, Gazz. Chim. Ital. 1995, 125, 431-435.
27. [4b] D. B. Amabilino, F. M. Raymo, J. F. Stoddart, Comprehensive Supra-molecular Chemistry, Vol. 9 (Eds.: M. W. Hosseini, J.-P. Sauvage), Pergamon, Oxford, 1996, 85-130.
28. [4c] R. E. Gillard, F. M. Raymo, J. F. Stoddart, Chem. Eur. J. 1997, 3, 1933-1940.
29. [4d] F. M. Raymo, J. F. Stoddart, Chemtracts 1998, 11, 491-511.
30. For accounts and reviews on [C-H⋯O] hydrogen bonds, see: [5a] G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296.
31. [5b] G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449.
32. [5c] T. Steiner Chem. Commun. 1997, 727-734.
33. [5d] I. Berger, M. Egli, Chem. Eur. J. 1997, 3, 1400-1404.
34. For accounts and reviews on [π⋯π] stacking interactions, see: [6a] M. H. Schwartz, J. Inclusion Phenom. 1990, 9, 1-35.
35. [6b] J. H. Williams, Acc. Chem. Res. 1993, 26, 593-598.
36. [6c] C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586; C. A. Hunter, J. Mol. Biol. 1993, 230, 1025-1054.
37. [6c] C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586; C. A. Hunter, J. Mol. Biol. 1993, 230, 1025-1054.
38. [6d] T. Dahl, Acta Chem. Scand. 1994, 48, 95-116.
39. [6e] F. Cozzi, J. S. Siegel, Pure Appl. Chem. 1995, 67, 683-689.
40. [6f] C. G. Claessens, J. F. Stoddart, J. Phys. Org. Chem. 1997, 10, 254-272.
41. For accounts and reviews on [C-H⋯π] interactions, see: [7a] M. Oki, Acc. Chem. Res. 1990, 23, 351-356.
42. [7b] M. C. Etter, J. Phys. Chem. 1991, 95, 4601-4610.
43. [7c] M. J. Zaworotko, Chem. Soc. Rev. 1994, 23, 283-288.
44. [7d] M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665-8701.
45. [7e] M. Nishio, Y. Umezawa, M. Hirota, The [C-H⋯π, Wiley-VCH, New York, 1998.
46. For reviews and accounts on template-directed syntheses, see: [8a] D. H. Busch, N. A. Stephenson, Coord. Chem. Rev. 1990, 100, 119-154.
47. [8b] J. S. Lindsey, New J. Chem. 1991, 15, 153-180.
48. [8c] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319.
49. [8d] D. Philp, J. F. Stoddart, Synlett 1991, 445-458.
50. [8e] D. H. Busch J. Inclusion Phenom. 1992, 12, 389-395.
51. [8f] S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475.
52. [8g] R. Cacciapaglia, L. Mandolini, Chem. Soc. Rev. 1993, 22, 221-231.
53. [8h] R. Hoss, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384.
54. [8i] J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187.
55. [8j] D. Philp, J. F Stoddart, Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196.
56. [8k] F. M. Raymo, J. F. Stoddart, Pure Appl. Chem. 1996, 68, 313-322.
57. [8l] M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401.
58. For examples of [2]rotaxanes incorporating 9-substituted anthracene stoppers, see: [9a] A. C. Benniston, A. Harriman, V. M. Lynch, Tetrahedron Lett. 1994, 35, 1473-1476.
59. [9b] A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291.
60. For a 9,10-dioxyanthracene-containing [2]catenane, see: R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, D. Marquis, L. Pérez-García, J. F. Stoddart, Eur. J. Org. Chem. 1998, 81-89.
61. 6, the singlet centered on δ = 4.10, corresponding to the protons of the "inside" 1,4-dioxybenzene ring, is partially overlapping with the resonances associated with the protons of the methylene groups of the polyether chains.
62. 1H-NMR spectrum of the free dumbbell-shaped compound 8, the singlet centered on δ = 6.80, corresponding to the protons of the two equivalent 1,4-dioxybenzene rings, is partially overlapping with the resonances associated with the protons on the two phenoxy rings of the stoppers which are in the ortho positions with respect to the oxygen atoms.
63. P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandolfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951.
64. C. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Dekker, New York, 1970.
65. P.-L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc., 1992, 114, 193-218.
66. B. S. Furniss, A. J. Hannaford, P. W. G. Smith, A. R. Tatchell, Practical Organic Chemistry, Longman, New York, 1989.
67. M. Ouchi, Y, Inoue, Y. Liu, S. Nagamura, S. Nakamura, K. Wada, T. Kakushi, Bull. Chem. Soc. Jpn. 1990, 63, 1260-1262.
68. A. Castellan, M. Daney, J. P. Desvergne, M. H. Riffaud, H. Bouas-Laurent, Tetrahedron Lett. 1983, 24, 5215-5218.
69. M. A. Petti, T. J. Shepodd, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1988, 110, 6825-6840.
70. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Compounds, Academic Press, London, 1965.