Anion-templated assembly of a [2]catenane

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15364-15365

  Sambrook, Mark R ^a   Beer, Paul D ^a   Wisner, James A ^a   Paul, Rowena L ^a   Cowley, Andrew R ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CATENANE; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL STRUCTURE; HYDROPHOBICITY; PH; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; X RAY DIFFRACTION;

EID: 9644270153     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045080b     Document Type: Article

References (37)

1. (a) Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Germany, 1999.
2. (b) Breault, G. A.; Hunter, C. A.; Meyers, P. C. Tetrahedron 1999, 55, 5265-5293.
3. (a) Pease, A. R.; Jeppeson, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. P.; Heatj, J. R. Acc. Chem. Res. 2001, 34 (6), 433-444.
4. (b) Schalley, C. A.; Beizai, K.; Vögtle, F. Acc. Chem. Res. 2001, 34 (6), 465-476.
5. (a) Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99 (7), 1643-1663.
6. (b) Flood, A. H.; Ramirez, R. J. A.; Deng, W.-Q.; Muller, R. P.; Goddard, W. A.; Stoddart, J. F. Aust. J. Chem. 2004, 57, 301-322.
7. (c) Try, A. C.; Harding, M. M.; Hamilton, D. G.; Sanders, J. K. M. Chem. Commun. 1998, 723-724.
8. (d) Loeb, S. J.; Wisner, J. A. Chem. Commun. 2000, 845-846.
9. (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114 (13), 5303-5311.
10. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619.
11. (c). Jonston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209.
12. (a) Blanco, M.-J.; Chambron, J.-C.; Jiménez, M. C.; Sauvage, J.-P. Top. Stereochem. 2003, 23, 125-173.
13. (b) Hogg, L.; Leigh, D. A.; Lusby, P. J.; Morelli, A.; Parsons, S.; Wong, J. K. Y. Angew. Chem., Int. Ed. 2004, 43 (10), 1218-1221.
14. (c) McArdle, C. P.; Irwin, M. J.; Jennings, M. C.; Puddephat, R. J. Angew. Chem., Int. Ed. 1999, 38 (22), 3376-3378.
15. (d) Vance, A. L.; Alcock, N. W.; Heppert, J. A.; Busch, D. H. Inorg. Chem. 1998, 37 (26), 6912-6920.
16. (e) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7 (19), 4142-4149.
17. (a) Anderson, S.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1956.
18. (b) Easton, C. J.; Lincoln, S. F.; Meyer, A. G.; Noagi, H. J. Chem. Soc., Perkin Trans, 1 1999, 2501-2506.
19. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
20. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
21. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
22. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
23. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
24. For some examples, see: (a) Seel, C.; Vögtle, F. Chem. Eur. J. 2000, 6 (1), 21-24. (b) Hübner, G. M.; Gläser, J.; Seel, C; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38 (3), 383-386. (c) Shukla, R.; Deetz, M. J.; Smith, B. D. Chem. Commun. 2000, 2397-2398. (d) Ghosh, P.; Mermagen, O.; Schalley, C. A. Chem. Commun. 2002, 2628-2629. (e) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224. (f) Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
25. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
26. (a) Wisner, J. A.; Beer, P. D.; Drew, M. G. B. Angew. Chem., Int. Ed. 2001, 40, 3606-3609.
27. (b) Wisner, J. A.; Beer, P. D.; Berry, N. G.; Tomapatanaget, B. PNAS 2002, 99 (8), 4983-4986.
28. (b) Curiel, D.; Beer, P. D.; Paul, R. L.; Cowley, A.; Sambrook, M. R.; Szemes, F. Chem. Commun. 2004, 1162-1163.
29. An anion-binding [2]-catenane structure has been reported, but no evidence for anion templation was observed: Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713.
30. Examples of the use of ring-closing metathesis in the formation of catenanes include: (a) Mobian, P.; Kern, J.-M.; Sauvage, J.-P. J Am. Chem. Soc. 2003, 125 (8), 2016-2017. (b) Leigh, D. A.; Lusby, P. J.; Teat, S. J.; Wilson, A. J. Wong, J. K. Y. Angew. Chem., Int. Ed. 2001, 40 (8), 1538-1543.
31. Examples of the use of ring-closing metathesis in the formation of catenanes include: (a) Mobian, P.; Kern, J.-M.; Sauvage, J.-P. J Am. Chem. Soc. 2003, 125 (8), 2016-2017. (b) Leigh, D. A.; Lusby, P. J.; Teat, S. J.; Wilson, A. J. Wong, J. K. Y. Angew. Chem., Int. Ed. 2001, 40 (8), 1538-1543.
32. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311-312.
33. Examples include: (a) Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713. (b) Deetz, M. J.; Shukla, R.; Smith, B. D. Tetrahedron 2002, 58, 799-805. (c) Kwan, P. H.; MacLachlan, M. J.; Swager, T. M. J. Am. Chem. Soc. 2004, 126, 8638-8639. (d) Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Aust. J. Chem. 2004, 57, 323-327. (e) Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124 (42), 12469-12476.
34. Examples include: (a) Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713. (b) Deetz, M. J.; Shukla, R.; Smith, B. D. Tetrahedron 2002, 58, 799-805. (c) Kwan, P. H.; MacLachlan, M. J.; Swager, T. M. J. Am. Chem. Soc. 2004, 126, 8638-8639. (d) Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Aust. J. Chem. 2004, 57, 323-327. (e) Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124 (42), 12469-12476.
35. Examples include: (a) Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713. (b) Deetz, M. J.; Shukla, R.; Smith, B. D. Tetrahedron 2002, 58, 799-805. (c) Kwan, P. H.; MacLachlan, M. J.; Swager, T. M. J. Am. Chem. Soc. 2004, 126, 8638-8639. (d) Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Aust. J. Chem. 2004, 57, 323-327. (e) Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124 (42), 12469-12476.
36. Examples include: (a) Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713. (b) Deetz, M. J.; Shukla, R.; Smith, B. D. Tetrahedron 2002, 58, 799-805. (c) Kwan, P. H.; MacLachlan, M. J.; Swager, T. M. J. Am. Chem. Soc. 2004, 126, 8638-8639. (d) Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Aust. J. Chem. 2004, 57, 323-327. (e) Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124 (42), 12469-12476.
37. Examples include: (a) Andrievsky, A.; Ahuis, F.; Sessler, J. L.; Vögtle, F.; Gudat, D.; Moini, M. J. Am. Chem. Soc. 1998, 120 (37), 9712-9713. (b) Deetz, M. J.; Shukla, R.; Smith, B. D. Tetrahedron 2002, 58, 799-805. (c) Kwan, P. H.; MacLachlan, M. J.; Swager, T. M. J. Am. Chem. Soc. 2004, 126, 8638-8639. (d) Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Aust. J. Chem. 2004, 57, 323-327. (e) Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124 (42), 12469-12476.