Origins of Selectivity in Molecular and Supramolecular Entities: Solvent and Electrostatic Control of the Translational Isomerism in [2]Catenanes

Journal of Organic Chemistry

Volumn 63, Issue 19, 1998, Pages 6523-6528

  Raymo, Francisco M ^a   Houk, K N ^a   Fraser Stoddart, J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000110161     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980543f     Document Type: Article

References (82)

1. For accounts and reviews on self-assembling approaches to [2]-catenanes, based on π-π stacking interactions, see: (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-458. (b) Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359. (c) Pasini, D.; Raymo, F. M.; Stoddart, J. F. Gazz. Chim. Ital. 1995, 125, 431-443. (d) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. Comprehensive Supramolecular Chemistry, Vol. 9; Hosseini, M. W., Sauvage, J.-P., Eds.; Pergamon Press: Cambridge, 1996; pp 85-130. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
2. For accounts and reviews on self-assembling approaches to [2]-catenanes, based on π-π stacking interactions, see: (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-458. (b) Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359. (c) Pasini, D.; Raymo, F. M.; Stoddart, J. F. Gazz. Chim. Ital. 1995, 125, 431-443. (d) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. Comprehensive Supramolecular Chemistry, Vol. 9; Hosseini, M. W., Sauvage, J.-P., Eds.; Pergamon Press: Cambridge, 1996; pp 85-130. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
3. For accounts and reviews on self-assembling approaches to [2]-catenanes, based on π-π stacking interactions, see: (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-458. (b) Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359. (c) Pasini, D.; Raymo, F. M.; Stoddart, J. F. Gazz. Chim. Ital. 1995, 125, 431-443. (d) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. Comprehensive Supramolecular Chemistry, Vol. 9; Hosseini, M. W., Sauvage, J.-P., Eds.; Pergamon Press: Cambridge, 1996; pp 85-130. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
4. For accounts and reviews on self-assembling approaches to [2]-catenanes, based on π-π stacking interactions, see: (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-458. (b) Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359. (c) Pasini, D.; Raymo, F. M.; Stoddart, J. F. Gazz. Chim. Ital. 1995, 125, 431-443. (d) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. Comprehensive Supramolecular Chemistry, Vol. 9; Hosseini, M. W., Sauvage, J.-P., Eds.; Pergamon Press: Cambridge, 1996; pp 85-130. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
5. For accounts and reviews on self-assembling approaches to [2]-catenanes, based on π-π stacking interactions, see: (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-458. (b) Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359. (c) Pasini, D.; Raymo, F. M.; Stoddart, J. F. Gazz. Chim. Ital. 1995, 125, 431-443. (d) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. Comprehensive Supramolecular Chemistry, Vol. 9; Hosseini, M. W., Sauvage, J.-P., Eds.; Pergamon Press: Cambridge, 1996; pp 85-130. (e) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933-1940.
6. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
7. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
8. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
9. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
10. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
11. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
12. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
13. For accounts and reviews on catenanes, see: (a) Schill, G. Catenaries, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Walba, D. M. Tetrahedron 1985, 47, 3161-3212. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (d) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248. (e) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (f) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (g) Belohradsky, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43; 1997, 62, 527-557.
14. For the synthesis and properties of the [2]catenane 1, see: (a) Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399. (b) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
15. For the synthesis and properties of the [2]catenane 1, see: (a) Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399. (b) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
16. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
17. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
18. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
19. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
20. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
21. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
22. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
23. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
24. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
25. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
26. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
27. In these [2]catenanes, π-π stacking interactions between the complementary π-electron deficient bipyridinium units and π-electron rich dioxyarene and/or dithiaarene units are observed. For accounts and reviews on π-π stacking interactions, see: (a) Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (c) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729-5733. (e) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598. (f) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (g) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 5330-5331. (h) Hunter, C. A. J. Mol. Biol. 1993, 230, 1025-1054. (i) Dahl, T. Acta Chem. Scand. 1994, 48, 95-116. (j) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (k) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027. (1) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
28. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
29. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
30. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
31. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
32. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
33. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
34. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
35. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
36. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
37. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
38. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
39. In these [2]catenanes, [CH⋯O] hydrogen bonding interactions between the acidic bipyridinium hydrogen atoms and the polyether oxygen atoms are observed. For accounts and reviews on hydrogen bonding interactions, see: (a) Etter, M. Acc. Chem. Res. 1990, 23, 120-126. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. (d) Hamilton, A. D. J. Chem. Educ. 1990, 67, 821-828. (e) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (f) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407. (g) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420. (h) Lehn, J. M. Pure Appl. Chem. 1994, 66, 1961-1966. (i) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573. (j) Burrows, A. D.; Chan, C. W.; Chowdhry, M. M.; McGrady, J. E.; Mingos, D. M. P. Chem. Soc. Rev. 1995, 24, 329-339. (k) Platts, J. A.; Howard, S. T.; Bracke, B. R. F. J. Am. Chem. Soc. 1996, 118, 2726-2733. (1) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
40. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
41. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
42. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
43. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
44. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
45. In these [2]catenanes, [CH⋯π] edge-to-face T-type interactions between the hydrogen atoms attached to the π-electron rich dioxyarene or dithiaarene units and the π-surfaces of the p-xylene spacers incorporated within the tetracationic cyclophane component are observed. For accounts and reviews on edge-to-face T-type interactions, see: (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201-7245. (b) Oki, M. Acc. Chem. Res. 1990, 23, 351-356. (c) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774. (d) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
46. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
47. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
48. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
49. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
50. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
51. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
52. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
53. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
54. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
55. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
56. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
57. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
58. For accounts and reviews on self-assembly processes, see: (a) Stoddart, J. F. In Chirality in Drug Design and Synthesis; Brown, C., Ed.; Academic Press: London, 1990; pp 53-81. (b) Mallouk, T. E.; Lee, H. J. Chem. Educ. 1990, 67, 829-834. (c) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 1450-1451. (d) Lindsey, J. S. New J. Chem. 1991, 15, 153-180. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (f) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44. (g) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669-671. (h) Ghadiri, M. R. Adv. Mater. 1995, 7, 675-677. (i) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079-1081. (1) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260. (m) Raymo, F. M.; Stoddart, J. F. Curr. Opin. Coll. Interface Sci. 1996, 1, 116-126. (n) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196. (o) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
59. For a discussion on the role of charge-transfer interactions in donor-acceptor complexes, see ref 4b and Morokuma, K. Acc. Chem. Res. 1977, 10, 294-300.
60. The term translational isomerism was first proposed by Schill, see: (a) Schill, G.; Rissler, K.; Fritz, H.; Vetter, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 187-189. Several translationally isomeric catenanes (ref 10) and rotaxanes have been self-assembled by us. For examples of translationally isomeric rotaxanes, see: (b) Anelli, P.-L.; Asakawa, M.; Ashton, P. R; Bissel, R. A.; Clavier, G.; Górski, R.; Kaifer, A. E.; Langford, S. J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. Chem. Eur. J., 1997, 3, 1113-1135 and references therein.
61. The term translational isomerism was first proposed by Schill, see: (a) Schill, G.; Rissler, K.; Fritz, H.; Vetter, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 187-189. Several translationally isomeric catenanes (ref 10) and rotaxanes have been self-assembled by us. For examples of translationally isomeric rotaxanes, see: (b) Anelli, P.-L.; Asakawa, M.; Ashton, P. R; Bissel, R. A.; Clavier, G.; Górski, R.; Kaifer, A. E.; Langford, S. J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. Chem. Eur. J., 1997, 3, 1113-1135 and references therein.
62. (a) Ashton, P. R.; Blower, M.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Ballardini, R.; Ciano, M.; Balzani, V.; Gandolfi, M. T.; Prodi, L.; McLean, C. H. New J. Chem. 1993, 17, 689-695.
63. (b) Amabilino, D. B.; Ashton, P. R.; Brown, G. R.; Hayes, W.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 2479-2482.
64. (c) Amabilino, D. B.; Anelli, P. L.; Ashton, P. R.; Brown, G. R.; Córdova, E.; Godínez, L. A.; Hayes, W.; Kaifer, A. E.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11142-11170.
65. (d) Ashton, P. R.; Huff, J.; Menzer, S.; Parsons, I. W.; Preece, J. P.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 31-44.
66. (e) Gillard, R. E.; Stoddart, J. F.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Org. Chem. 1996, 61, 4504-4505.
67. (f) Asakawa, M.; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26-37.
68. (g) Asakawa, M.; Ashton, P. R.; Dehaen, W.; L'Abbé, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; Toppet, S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1997, 3, 772-787.
69. (h) Ballardini, R.; Balzani, V.; Credi, A.; Brown, C. L., Gillard, R. E., Montalti, M., Philp, D., Stoddart, J. F., Venturi, M.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 12503-12513.
70. 2O. The resulting structures were subjected individually to Monte Carlo conformational searches. The complexes were constructed manually by docking the
71. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379-4386.
72. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, V. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784.
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75. Pollster, P.; Murray, J. S. Reviews in Computational Chemistry; Lipkowits, K. B., Boyd, D. B., Eds.; VCH: New York, 1991; Vol. 2, Chapter 7.
76. The tetracationic cyclophane component was removed from the global minima of the complexes obtained from the Monte Carlo conformational searches. Similarly, the polyether substituents, attached to the aromatic units of the guests, were replaced by methoxy groups without modifying the dihedral angles around the Ar-O bonds. The resulting compounds were subjected individually to single point ab initio calculations performed at the HF/6-31G** level employing the program Spartan 4.1.
77. Spartan V 4.1, Wavefunction, Inc., 18401 Von Karman Ave., Irvine CA 92715.
78. 3.
79. p. Thus, the ΔE value associated with the complex [10-13], and derived from the molecular mechanics calculations, is significantly over estimated.
80. A similar result was observed for the binding of metal cations by aromatic compounds, see: (a) Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. (b) Dougherty, D. A. Science 1996, 271, 163-168. (c) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
81. A similar result was observed for the binding of metal cations by aromatic compounds, see: (a) Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. (b) Dougherty, D. A. Science 1996, 271, 163-168. (c) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
82. A similar result was observed for the binding of metal cations by aromatic compounds, see: (a) Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308. (b) Dougherty, D. A. Science 1996, 271, 163-168. (c) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.