Quantitative comparison of kinetic stabilities of metallomacrocycle-based rotaxanes

Chemistry - A European Journal

Volumn 9, Issue 7, 2003, Pages 1535-1541

  Chang, Sung Youn ^a   Jang, Hye Young ^a   Jeong, Kyu Sung ^a  

^a Yonsei University   (South Korea)

Author keywords

Kinetic stability; Metallomacrocycles; Rotaxanes; Self assembly

Indexed keywords

ACTIVATION ENERGY; CHROMATOGRAPHY; ENTHALPY; ENTROPY; FREE ENERGY; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; SILICA GEL; TRANSITION METALS;

KINETIC STABILITIES;

REACTION KINETICS;

MACROCYCLIC COMPOUND; METALLOMACROCYCLIC DERIVATIVE; OSMIUM; PALLADIUM; PLATINUM; RHENIUM; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION KINETICS; ENTHALPY; ENTROPY; EQUILIBRIUM CONSTANT; HYDROGEN BOND; KINETIC STABILITY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS; TWO DIMENSIONAL EXCHANGE SPECTROSCOPY;

EID: 0037419447     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390176     Document Type: Article

References (93)

1. For reviews on molecular machines see: a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391; b) special issue on molecular machines: Acc. Chem. Res. 2001, 34, 412-522.
2. For reviews on molecular machines see: a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391; b) special issue on molecular machines: Acc. Chem. Res. 2001, 34, 412-522.
3. For reviews on molecular machines see: a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391; b) special issue on molecular machines: Acc. Chem. Res. 2001, 34, 412-522.
4. a) J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256-1261; Angew. Chem. Int. Ed. 2001, 40, 1216-1221;
5. a) J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256-1261; Angew. Chem. Int. Ed. 2001, 40, 1216-1221;
6. b) A. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel, Science, 2001, 291, 2124-2128;
7. c) G. W. H. Wurpel, A. M. Brouwer, I. H. M. van Stokkum, A. Farran, D.A. Leigh, J. Am. Chem. Soc. 2001, 123, 11327-11328;
8. d) C. P. Collier, J. O. Jeppesen, Y. Luo, J. Perkins, E. W. Wong, J. R. Heath, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 12632-12641;
9. e) R. Ballardini, V. Balzani, M. Clemente-León, A. Credi, M. T. Gandolfi, E. Ishow, J. Perkins, J. F. Stoddart, H.-R. Tseng, S. Wenger. J. Am. Chem. Soc. 2002, 124, 12786-12795;
10. f) C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847-1850; Angew. Chem. Int. Ed. 2002, 41, 1769-1772;
11. f) C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847-1850; Angew. Chem. Int. Ed. 2002, 41, 1769-1772;
12. g) M. C. Jimenez-Molero, C. Dietrich-Buchecker, J.-P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466.
13. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
14. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
15. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
16. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
17. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
18. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
19. For reviews on pseudorotaxanes and rotaxanes, see: a) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944; b) J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366; c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976; d) C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; e) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52; f) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107.
20. a) J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Org. Lett. 2000, 2, 3547-3550;
21. b) A. Arduini, R. Ferdani, A. Pochini, A. Secchi, F. Ugozzoli, Angew. Chem. 2000, 112, 3595-3598; Angew. Chem. Int. Ed. 2000, 39, 3453-3456;
22. b) A. Arduini, R. Ferdani, A. Pochini, A. Secchi, F. Ugozzoli, Angew. Chem. 2000, 112, 3595-3598; Angew. Chem. Int. Ed. 2000, 39, 3453-3456;
23. c) M. J. MacLachlan, A. Rose, T. M. Swager, J. Am. Chem. Soc. 2001, 123, 9180-9181;
24. d) X. Zhao, X.-K. Jiang, M. Shi, Y.-H. Yu, W. Xia, Z.-T. Li, J. Org. Chem. 2001, 66, 7035-7043;
25. e) J. M. Mahoney, R. Shukla, R. A. Marshall, A. M. Beatty, J. Zajicek, B. D. Smith, J. Org. Chem. 2002, 67, 1436-1440;
26. f) J. A. Wisner, P. D. Beer, M. G. B. Drew, M. R. Sambrook, J. Am. Chem. Soc. 2002, 124, 12469-12476;
27. g) M. Andersson, M. Linke, J.-C. Chambron, J. Davidsson, V. Heitz, L. Hammarström, J.-P. Sauvage, J. Am. Chem. Soc. 2002, 124, 4347-4362.
28. For recent examples of lactam macrocycle-based rotaxanes, see: a) C. Reuter, W. Wienand, C. Schmuck, F. Vögtle. Chem. Eur. J. 2001, 7, 1728-1733; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) M. Asakawa, G. Brancato, M. Fanti, D. A. Leigh, T. Shimizu, A. M. Z. Slawin, J. K. Y. Wong, F. Zerbetto, S. Zhang, J. Am. Chem. Soc. 2002, 124, 2939-2950; d) C. A. Schalley, G. Silva, C. F. Nising, P. Linnartz, Helv. Chim. Acta 2002, 85, 1578-1596.
29. For recent examples of lactam macrocycle-based rotaxanes, see: a) C. Reuter, W. Wienand, C. Schmuck, F. Vögtle. Chem. Eur. J. 2001, 7, 1728-1733; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) M. Asakawa, G. Brancato, M. Fanti, D. A. Leigh, T. Shimizu, A. M. Z. Slawin, J. K. Y. Wong, F. Zerbetto, S. Zhang, J. Am. Chem. Soc. 2002, 124, 2939-2950; d) C. A. Schalley, G. Silva, C. F. Nising, P. Linnartz, Helv. Chim. Acta 2002, 85, 1578-1596.
30. For recent examples of lactam macrocycle-based rotaxanes, see: a) C. Reuter, W. Wienand, C. Schmuck, F. Vögtle. Chem. Eur. J. 2001, 7, 1728-1733; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) M. Asakawa, G. Brancato, M. Fanti, D. A. Leigh, T. Shimizu, A. M. Z. Slawin, J. K. Y. Wong, F. Zerbetto, S. Zhang, J. Am. Chem. Soc. 2002, 124, 2939-2950; d) C. A. Schalley, G. Silva, C. F. Nising, P. Linnartz, Helv. Chim. Acta 2002, 85, 1578-1596.
31. For recent examples of lactam macrocycle-based rotaxanes, see: a) C. Reuter, W. Wienand, C. Schmuck, F. Vögtle. Chem. Eur. J. 2001, 7, 1728-1733; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) M. Asakawa, G. Brancato, M. Fanti, D. A. Leigh, T. Shimizu, A. M. Z. Slawin, J. K. Y. Wong, F. Zerbetto, S. Zhang, J. Am. Chem. Soc. 2002, 124, 2939-2950; d) C. A. Schalley, G. Silva, C. F. Nising, P. Linnartz, Helv. Chim. Acta 2002, 85, 1578-1596.
32. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
33. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
34. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
35. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
36. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
37. For recent examples of crown ether macrocycle-based rotaxanes, see: a) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2002, 8, 5170-5183; b) J. Tiburcio, G. J. E. Davidson, S. J. Loeb, Chem. Commun. 2002, 1282-1283; c) Y. Tokunaga, T. Seo, Chem. Commun. 2002, 970-971; d) H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653-4665; e) S.-H. Chiu, A. M. Elizarov, P. T. Glink, J. F. Stoddart, Org. Lett. 2002, 4, 3561-3564; f) Y. Furusho, G. A. Rajkumar, T. Oku, T. Takata, Tetrahedron 2002, 58, 6609-6613.
38. For cyclodextrin-based rotaxanes, see: a) H. Shigekawa, K. Miyake, J. Sumaoka, A. Harada, M Komiyama, J. Am. Chem. Soc. 2000, 122, 5411-5412;
39. b) T. Fujimoto, Y. Sakata, T. Kaneda, Chem. Commun. 2000, 2143-2144;
40. c) I. Yamaguchi, K. Osakada, T. Yamamoto, Chem. Commun. 2000, 1335-1336;
41. d) H. Onagi, C. J. Easton, S. F. Lincoln, Org. Lett. 2001, 3, 1041-1044;
42. e) C. A. Stanier, M. J. O'Connell, W. Clegg, H. L. Anderson, Chem. Commun. 2001, 493-494.
43. For reviews see: a) M. Fujita, Chem. Soc. Rev. 1998, 27, 417- 425;
44. b) C. J. Jones, Chem. Soc. Rev. 1998, 27, 289-299;
45. c) R. V. Slone, K. D. Benkstein, S. Bélanger, J. T. Hupp, I. A. Guzei, A. L. Rheingold, Coord. Chem. Rev. 1998, 171, 221-243;
46. d) S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-908;
47. e) B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076-2097; Angew. Chem. Int. Ed. 2001, 40, 2022-2043;
48. e) B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076-2097; Angew. Chem. Int. Ed. 2001, 40, 2022-2043;
49. f) S.-S. Sun, A. J. Lees, Coord. Chem. Rev. 2002, 230, 171-192.
50. a) V. Balzani, A. Juris, M. Venturi, Chem. Rev. 1996, 96, 759-833;
51. b) L. Fabbrizzi, M. Licchelli, P. Pallavicini, Acc. Chem. Res. 1999, 32, 846-853.
52. a) P. R. Ashton, V. Balzani, O. Kocian, L. Prodi, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 11190-11191;
53. b) J.-P. Sauvage, Acc. Chem. Res. 1998, 31, 611-619.
54. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
55. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
56. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
57. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
58. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
59. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
60. For rotaxanes containing transition metals on the thread components, see: a) H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304; b) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; c) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334; d) S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758; e) K. Chichak, M.C. Walsh, N.R. Branda, Chem. Commun. 2000, 847-848; f) A.D. Shukla, H. C. Bajaj, A. Das, Angew. Chem. 2001, 113, 460-462; Angew. Chem. Int. Ed. 2001, 40, 446-448.
61. a) K.-S. Jeong, J. S. Choi, S.-Y. Chang, H.-Y. Chang, Angew. Chem. 2000, 112, 1758-1761; Angew. Chem. Int. Ed. 2000, 39, 1692-1695;
62. a) K.-S. Jeong, J. S. Choi, S.-Y. Chang, H.-Y. Chang, Angew. Chem. 2000, 112, 1758-1761; Angew. Chem. Int. Ed. 2000, 39, 1692-1695;
63. b) S.-Y. Chang, J. S. Choi, K.-S. Jeong, Chem. Eur. J. 2001, 7, 2687-2697.
64. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
65. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
66. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
67. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
68. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
69. For systematic studies on the effect of stopper sizes on the kinetic stability of rotaxanes, see: a) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Bělohradský, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310; b) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 2297-2307; c) F. M. Raymo, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 9318-9322; d) C. Heim, A. Affeld, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 746-759; e) G. M. Hübner, G. Nachtsheim, Q. Y. Li, C. Seel, F. Vögtle, Angew. Chem. 2000, 112, 1315-1318; Angew. Chem. Int. Ed. 2000, 39, 1269-1272.
70. For the charge effect on the kinetic stability of rotaxanes, see: Y. Kawaguchi, A. Harada, J. Am. Chem. Soc. 2000, 122, 3797-3798.
71. For self-assembly of zinc porphyrin based rotaxanes, see C. A. Hunter, C. M. R. Low, M. J. Packer, S. E. Spey, J. G. Vinter, M. O. Vysotsky, C. Zonta, Angew. Chem. 2001, 113, 2750-2754; Angew. Chem. Int. Ed. 2001, 40, 2678-2682.
72. For self-assembly of zinc porphyrin based rotaxanes, see C. A. Hunter, C. M. R. Low, M. J. Packer, S. E. Spey, J. G. Vinter, M. O. Vysotsky, C. Zonta, Angew. Chem. 2001, 113, 2750-2754; Angew. Chem. Int. Ed. 2001, 40, 2678-2682.
73. For the catenane system with similar concept, see: a) M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176; b) M. Fujita, Acc. Chem. Res. 1999, 32, 53-61.
74. For the catenane system with similar concept, see: a) M. Fujita, F. Ibukuro, K. Yamaguchi, K. Ogura, J. Am. Chem. Soc. 1995, 117, 4175-4176; b) M. Fujita, Acc. Chem. Res. 1999, 32, 53-61.
75. a) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 502-518;
76. b) L. R. MacGillivray, J. L. Atwood, Angew. Chem. 1999, 111, 1080-1096; Angew. Chem. Int. Ed. 1999, 38, 1018-1033;
77. b) L. R. MacGillivray, J. L. Atwood, Angew. Chem. 1999, 111, 1080-1096; Angew. Chem. Int. Ed. 1999, 38, 1018-1033;
78. c) G. F. Swiegers, T. J. Malefetse, Chem. Rev. 2000, 100, 3483-3537;
79. d) G. F. Swiegers, T. J. Malefetse, Coord. Chem. Rev. 2002, 225, 91-121;
80. e) S. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972-983.
81. a) K.-S. Jeong, J. W. Lee, T.-Y. Park, S.-Y. Chang, Chem. Commun. 1999, 2069-2070; for dinuclear analogues of the bead, see:
82. b) K.-S. Jeong, Y. L. Cho, J. U. Song, H.-Y. Chang, M. G. Choi, J. Am. Chem. Soc. 1998, 120, 10982-10983;
83. c) K.-S. Jeong, Y. L. Cho, S.-Y. Chang, T.-Y. Park, J. U. Song, J. Org. Chem. 1999, 64, 9459-9466.
84. a) C. L. Perrin, T. J. Dwyer, Chem. Rev. 1990, 90, 935-967;
85. b) D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225;
86. c) F. Hof, C. Nuckolls, S.L. Craig, T. Martín, J. Rebek, Jr., J. Am. Chem. Soc. 2000, 122, 10991-10996;
87. d) M. Cai, V. Sidorov, Y.-F. Lam, R. A. Flowers, II, J. T. Davis, Org. Lett. 2000, 2, 1665-1668;
88. e) M. Pons, O. Millet, Prog. Nucl. Magn. Reson. Spectrosc. 2001, 38, 267-324.
89. Details for the equation including experimental treatments are described in the Supporting Information. For a similar study, see reference [13a].
90. a) H. Friebolin, Basic One- and Two-Dimensional NMR Spectroscopy, VCH, Weinheim (Germany), 1991, pp. 269-273;
91. b) A. Affeld, G. M. Hübner, C. Seel, C. A. Schally, Eur. J. Org. Chem. 2001, 2877-2890.
92. P. J. Stang, D. H. Cao, S. Saito, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 6273-6283.
93. R. S. Macomber, J. Chem. Educ. 1992, 69, 375-378.