Doubly docked pseudorotaxanes

Chemistry - A European Journal

Volumn 4, Issue 8, 1998, Pages 1523-1534

  Ashton, Peter R ^a   Fyfe, Matthew C T ^a   Martínez Díaz, M Victoria ^a   Menzer, Stephan ^b   Schiavo, Cesare ^a   Stoddart, J Fraser ^a,c   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Host guest chemistry; Inclusion compounds; Molecular recognition; Pseudorotaxanes; Supramolecular devices

Indexed keywords

EID: 0031829504     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980807)4:8<1523::AID-CHEM1523>3.0.CO;2-V     Document Type: Article

References (67)

1. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
2. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
3. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
4. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
5. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
6. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
7. The term rotaxane derives ( G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971, p. 3 ) from the Latin words rota, meaning wheel, and axis, meaning axle. In these molecular compounds, one or more wheel and axle components are constrained to be bound to one another mechanically, since the axle(s) is/are endowed with bulky stopper groups that prevent the extrusion of the wheel(s). The addition of the appendage pseudo indicates (P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679) that the wheel(s) is/are free to dissociate from the axle(s), that is, that they are, in actual fact, similar to conventional complexes. Consequently, in chemical terms, the complementary molecular components of pseudorotaxanes are held together principally by attractive noncovalent bonds. The number of components of which rotaxanes and pseudorotaxanes are comprised is indicated by the prefix [n]. See: a) D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, L. A. Godínez, 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; b) P. R. Ashton, S. J. Langford, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1996, 1387-1388; c) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Airola, K. Rissanen, Inorg. Chem. 1997, 36, 4734-4742; d) A. Mirzoian, A. E. Kaifer, Chem. Eur. J. 1997, 3, 1052-1058. However, it has been shown recently that all pseudorotaxanes are held together, to a certain extent, by mechanical bonding interactions. See: e) 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.
8. a) J. C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162;
9. b) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828;
10. c) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.
11. c) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944.
12. M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401.
13. a) D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260;
14. b) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196:
15. b) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196:
16. c) M. M. Conn. J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
17. d) R. E. Gillard, F. M. Raymo, J. F. Stoddart, Chem. Eur. J. 1997, 3, 1933-1940:
18. e) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680.
19. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Sloddart, P. A. Tusker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001; Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869;
20. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Sloddart, P. A. Tusker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001; Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869;
21. b) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1871
22. b) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1871
23. c) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728;
24. d) P. T. Glink, C. Schiavo, J. F. Stoddart, D. J. Williams, Chem. Commun. 1996, 1483-1490;
25. e) P. R. Ashton, P. T. Glink, M.-V. Martínez-Díaz, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1996, 108, 2058-2061; Angew. Chem. Int. Ed. Engl. 1996, 35, 1930-1933;
26. e) P. R. Ashton, P. T. Glink, M.-V. Martínez-Díaz, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1996, 108, 2058-2061; Angew. Chem. Int. Ed. Engl. 1996, 35, 1930-1933;
27. f) M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1997, 109, 2158-2160; Angew. Chem. Int. Ed. Engl. 1997, 36, 2068-2070;
28. f) M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1997, 109, 2158-2160; Angew. Chem. Int. Ed. Engl. 1997, 36, 2068-2070;
29. g) P. R. Ashton, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 12514-12524.
30. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995, pp. 37-53, and references therein.
31. For leading references on molecular switches, see: V. Balzani, M. Gómez-López, J. F. Stoddart, Acc. Chem. Res., in press.
32. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 59-62; Angew. Chem. Int. Ed. Engl. 1997, 36, 59-62;
33. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 59-62; Angew. Chem. Int. Ed. Engl. 1997, 36, 59-62;
34. b) M. C. Feiters, M. C. T. Fyfe, M.-V. Martínez-Díaz, S. Menzer, R. J. M. Nolle, J. F. Stoddart, P. J. M. van Kan, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 8119-8120.
35. We have utilized the complexation of BPP34C10 with 4,4′-bipyridinium units previously for the synthesis of rotaxanes and the supramolecular synthesis of pseudorotaxanes. See: 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, and references therein.
36. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 756-759; Angew. Chem. Int. Ed. Engl. 1997, 36, 735-739;
37. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 756-759; Angew. Chem. Int. Ed. Engl. 1997, 36, 735-739;
38. b) P. R. Ashton, M. C. T. Fyfe, S. K. Hickingbottom, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 577-589.
39. [5f-g] suggested by the modeling procedures being largely reflected in the co-conformations of the real structures.
40. [5f-g] suggested by the modeling procedures being largely reflected in the co-conformations of the real structures.
41. [5f-g] suggested by the modeling procedures being largely reflected in the co-conformations of the real structures.
42. 14.
43. C. A. Hunter, Chem. Soc. Rev. 1994, 23, 101-109.
44. [5f-g] to characterize the three-dimensional spatial arrangement of the atoms in molecular and supramolecular entities that are comprised of two or more distinct components. Two different co-conformations may be envisaged for the complexes generated from the association of macrocyclic and threadlike species. A complex with a face-to-face co-conformation is produced when the faces of the two distinct chemical species lie alongside one another, while a pseudorotaxane co-conformation originates when the threadlike component interpenetrates the cavity of the macrocycle.
45. I. Goldberg, in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic Press, London, 1984, pp. 261-335.
46. a) M. Nishio, Y. Umeczawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8865-8701;
47. b) H. Adams, K. D. M. Harris, G. A. Hembury, C. A. Hunter, D. Livingstone, J. F. McCabe, Chem. Commun. 1996, 2531-2532.
48. For recent reviews describing the state-of-the-art in anion recognition, see: a) P. D. Beer, Chem. Commun, 1996, 689-696; b) J. Scheerder, J. F. J. Engbersen, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1996, 115, 307-320; c) J. L. Atwood, K. T. Holman, J. W. Steed, Chem. Commun. 1996, 1401-1407; d) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
49. For recent reviews describing the state-of-the-art in anion recognition, see: a) P. D. Beer, Chem. Commun, 1996, 689-696; b) J. Scheerder, J. F. J. Engbersen, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1996, 115, 307-320; c) J. L. Atwood, K. T. Holman, J. W. Steed, Chem. Commun. 1996, 1401-1407; d) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
50. For recent reviews describing the state-of-the-art in anion recognition, see: a) P. D. Beer, Chem. Commun, 1996, 689-696; b) J. Scheerder, J. F. J. Engbersen, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1996, 115, 307-320; c) J. L. Atwood, K. T. Holman, J. W. Steed, Chem. Commun. 1996, 1401-1407; d) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
51. For recent reviews describing the state-of-the-art in anion recognition, see: a) P. D. Beer, Chem. Commun, 1996, 689-696; b) J. Scheerder, J. F. J. Engbersen, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1996, 115, 307-320; c) J. L. Atwood, K. T. Holman, J. W. Steed, Chem. Commun. 1996, 1401-1407; d) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
52. M.-V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907.
53. M.-V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907.
54. 2.
55. D. B. Smithrud, F. Diederich, J. Am. Chem. Soc. 1990, 112, 339-343.
56. For some other examples of cooperative systems, see: a) B. Perlmutter-Hayman, Acc. Chem. Res. 1986, 19, 90-96; b) A. Pfeil, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1992, 838-840; c) R. S. Lokey, Y. Kwok, V. Guelev, C. J. Pursell, L. H. Hurley, B. L. Iverson, J. Am. Chem. Soc. 1997, 119, 7202-7210.
57. For some other examples of cooperative systems, see: a) B. Perlmutter-Hayman, Acc. Chem. Res. 1986, 19, 90-96; b) A. Pfeil, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1992, 838-840; c) R. S. Lokey, Y. Kwok, V. Guelev, C. J. Pursell, L. H. Hurley, B. L. Iverson, J. Am. Chem. Soc. 1997, 119, 7202-7210.
58. For some other examples of cooperative systems, see: a) B. Perlmutter-Hayman, Acc. Chem. Res. 1986, 19, 90-96; b) A. Pfeil, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1992, 838-840; c) R. S. Lokey, Y. Kwok, V. Guelev, C. J. Pursell, L. H. Hurley, B. L. Iverson, J. Am. Chem. Soc. 1997, 119, 7202-7210.
59. A. P. de Silva, H. Q. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566, and references therein.
60. 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.
61. J. Homer, M. C. Perry, J. Chem. Soc. Chem. Commun. 1994, 373-374.
62. M. S. Newman, L. F. Lee, J. Org. Chem. 1972, 37, 4468-4469.
63. W. Ried, H. Bodem, U. Ludwig, H. Neidhardt, Chem. Ber. 1958, 91, 2479-2484.
64. A. J. Hofnagel, Recl. Trav. Chim. Pays-Bas 1992, 111, 22-28.
65. J. M. Bollinger, M. B. Comisarow, C. A. Cupas, G. A. Olah, J. Am. Chem. Soc. 1967, 89, 5678-5691.
66. A. Altomare, M. C. Burla, M. Camelli, G. Cascarano, C Giacovazzo, A. Gualiardi, G. Polidori, University of Bari, Italy, 1992.
67. SHELXTL PC V 5.03, Siemens Analytical X-Ray Instruments, Madison, WI, 1994.