Enantioselective discrimination in the self-assembly of [2]pseudorotaxanes

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 983-986

  Asakawa, Masumi ^a   Janssen, Henk M ^b   Meijer, E W ^b   Pasini, Dario ^a   Stoddart, J Fraser ^a,c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^c Dept of Chemistry and Biochemistry ^*  (United States)

Author keywords

CD spectroscopy; Chirality; Enantioselective receptors; Host guest chemistry; Self assembly

Indexed keywords

EID: 2742605837     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<983::AID-EJOC983>3.0.CO;2-W     Document Type: Article

References (36)

1. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
2. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
3. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
4. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
5. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
6. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
7. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
8. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
9. For a recent review on enantioselective and diastereoselective molecular recognition involving neutral chiral molecules, see: T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395. For important examples of enantioselective recognition, see: [1a] W. C. Still, Acc. Chem. Res. 1996, 29, 155-163. [1b] B. Winterwerner, F. Diederich, V. Gramlich, Helv. Chim. Acta 1996, 79, 1338-1360. [1c] J. E. Forman, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1995, 117, 9213-9228. [1d] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S. Inoue, J. Am. Chem. Soc. 1994, 116, 1337-1344. [1e] A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1992, 114, 1511-1512. [1f] T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555. [1g] M. Famulok, K. S. Jeong, G. Deslongchamps, J. Rebek, Jr., Angew. Chem., Int. Ed. Engl. 1991, 30, 858-860; Angew. Chem. 1991, 103, 880-882.
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12. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
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14. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
15. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
16. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
17. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
18. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
19. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
20. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
21. For articles on chemical and biological self-assembly processes, see: [3a] J. S. Lindsey, New J. Chem. 1991, 15, 153-180. [3b] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319. [3c] D. Philp, J. F. Stoddart, Synlett 1991, 445-458. [3d] G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44. [3e] D. Philp, J. F. Stoddart, Angew. Chem. Int Ed. Engl. 1996, 35, 1154-1196; Angew. Chem. 1996, 108, 1242-1286. [3f] M C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401. [3g] M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668. [3h] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680. [3i] R. E. Gillard, F. M. Raymo. J. F. Stoddart, Eur. J. Chem. 1997, 3, 1933-1940.
22. D. B. Amabilino, J. F. Stoddart, Chem Rev. 1995, 95, 2725-2828.
23. Pseudorotaxanes have been defined (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1991, 1677-1679) as the non-interlocked counterparts of rotaxanes, in which one or more linear "threads" interpenetrate the cavities of one or more macrocycles to form inclusion complexes. Notably, as distinct from rotaxanes, these supramolecular complexes are free to dissociate into their separate components, since they do not possess bulky stopper groups. For some recent examples, see: [5a] D. B. Amabilino, R-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. [5b] p. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388. [5c] H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742. [5d] A. Mirzoian, A. E. Kaifer, Chem. Eur. J 1997, 3, 1052-1058.
24. Pseudorotaxanes have been defined (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1991, 1677-1679) as the non-interlocked counterparts of rotaxanes, in which one or more linear "threads" interpenetrate the cavities of one or more macrocycles to form inclusion complexes. Notably, as distinct from rotaxanes, these supramolecular complexes are free to dissociate into their separate components, since they do not possess bulky stopper groups. For some recent examples, see: [5a] D. B. Amabilino, R-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. [5b] p. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388. [5c] H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742. [5d] A. Mirzoian, A. E. Kaifer, Chem. Eur. J 1997, 3, 1052-1058.
25. Pseudorotaxanes have been defined (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1991, 1677-1679) as the non-interlocked counterparts of rotaxanes, in which one or more linear "threads" interpenetrate the cavities of one or more macrocycles to form inclusion complexes. Notably, as distinct from rotaxanes, these supramolecular complexes are free to dissociate into their separate components, since they do not possess bulky stopper groups. For some recent examples, see: [5a] D. B. Amabilino, R-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. [5b] p. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388. [5c] H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742. [5d] A. Mirzoian, A. E. Kaifer, Chem. Eur. J 1997, 3, 1052-1058.
26. Pseudorotaxanes have been defined (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1991, 1677-1679) as the non-interlocked counterparts of rotaxanes, in which one or more linear "threads" interpenetrate the cavities of one or more macrocycles to form inclusion complexes. Notably, as distinct from rotaxanes, these supramolecular complexes are free to dissociate into their separate components, since they do not possess bulky stopper groups. For some recent examples, see: [5a] D. B. Amabilino, R-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. [5b] p. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388. [5c] H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742. [5d] A. Mirzoian, A. E. Kaifer, Chem. Eur. J 1997, 3, 1052-1058.
27. Pseudorotaxanes have been defined (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc., Chem. Commun. 1991, 1677-1679) as the non-interlocked counterparts of rotaxanes, in which one or more linear "threads" interpenetrate the cavities of one or more macrocycles to form inclusion complexes. Notably, as distinct from rotaxanes, these supramolecular complexes are free to dissociate into their separate components, since they do not possess bulky stopper groups. For some recent examples, see: [5a] D. B. Amabilino, R-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11142-11170. [5b] p. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388. [5c] H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742. [5d] A. Mirzoian, A. E. Kaifer, Chem. Eur. J 1997, 3, 1052-1058.
28. The synthetic procedure employed in the synthesis of the compounds 3-5 has been reported elsewhere. See: 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.
29. -3 M with respect to each component) proportions with the cyclophanes. For all of the 1:1 complexes investigated, and therefore also within enantiomeric pairs of substrates, the hydroquinone ring protons resonate with different chemical shifts.
30. 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.
31. 1-NMR-spectroscopic data and the titration curves for all the [2]pseudorotaxanes investigated are consistent with the expected 1:1 host/guest stoichiometry.
32. K. A. Connors, Binding Constants, Wiley, New York, 1987.
33. For books on circular dichroism see: [11a] K. Nakanishi, N. Berova, R. W. Woody Circular Dichroism, Principles and Applications, VCH Publishers, Inc., New York, 1994. - [11b] E. L. Eliel, S. H. Wilen, Stereochemistry of Organic: Compounds, Wiley, New York, 1994. - [11c] N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy, Exciton Coupling in Organic Stereochemistry, Oxford University Press, Oxford, 1983.
34. For books on circular dichroism see: [11a] K. Nakanishi, N. Berova, R. W. Woody Circular Dichroism, Principles and Applications, VCH Publishers, Inc., New York, 1994. - [11b] E. L. Eliel, S. H. Wilen, Stereochemistry of Organic: Compounds, Wiley, New York, 1994. - [11c] N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy, Exciton Coupling in Organic Stereochemistry, Oxford University Press, Oxford, 1983.
35. For books on circular dichroism see: [11a] K. Nakanishi, N. Berova, R. W. Woody Circular Dichroism, Principles and Applications, VCH Publishers, Inc., New York, 1994. - [11b] E. L. Eliel, S. H. Wilen, Stereochemistry of Organic: Compounds, Wiley, New York, 1994. - [11c] N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy, Exciton Coupling in Organic Stereochemistry, Oxford University Press, Oxford, 1983.
36. M. Asakawa, P. R. Ashton, G. R. Brown, W. Hayes, S. Menzer, J. F. Stoddart, A. J. P. White, D J. Williams, Adv. Mater. 1996, 8, 37-41.