Structural Homology and Dynamic Variation in a Series of Porphyrin Bipyridinium Receptors and Their [2]Catenanes

European Journal of Organic Chemistry

Volumn , Issue 1, 2004, Pages 193-208

  Gunter, Maxwell J ^a   Jeynes, Tyrone P ^a   Turner, Peter ^b  

^a UNIVERSITY OF NEW ENGLAND   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Bipyridinium; Catenanes; Dynamics; Porphyrins; Receptors

Indexed keywords

BIPYRIDINE; CATENANE; DIETHYLENE; ETHYLENE; HYDROQUINONE; MACROGOL; NAPHTHOQUINONE; OLIGOMER; PARAQUAT; PORPHYRIN; RECEPTOR; TETRAETHYLENE; TRIETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATENATION; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTRON; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SURFACE CHARGE; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY ANALYSIS;

EID: 1942438855     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300493     Document Type: Article

References (62)

1. A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Research 2001, 34, 433. J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89. V. Balzani, A. Credi, M. Venturi, Chem. Eur. J. 2002, 8, 5525.
2. A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Research 2001, 34, 433. J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89. V. Balzani, A. Credi, M. Venturi, Chem. Eur. J. 2002, 8, 5525.
3. A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Research 2001, 34, 433. J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89. V. Balzani, A. Credi, M. Venturi, Chem. Eur. J. 2002, 8, 5525.
4. V. Balzani, M. Gómez-Lopez, J. F. Stoddart, Acc. Chem. Research 1998, 31, 405. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3349. B. L. Feringa, Acc. Chem. Research 2001, 34, 504. J. F. Stoddart, Chem. Aust. 1992, 576. J. F. Stoddart, Acc. Chem. Research 2001, 34, 410.
5. V. Balzani, M. Gómez-Lopez, J. F. Stoddart, Acc. Chem. Research 1998, 31, 405. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3349. B. L. Feringa, Acc. Chem. Research 2001, 34, 504. J. F. Stoddart, Chem. Aust. 1992, 576. J. F. Stoddart, Acc. Chem. Research 2001, 34, 410.
6. V. Balzani, M. Gómez-Lopez, J. F. Stoddart, Acc. Chem. Research 1998, 31, 405. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3349. B. L. Feringa, Acc. Chem. Research 2001, 34, 504. J. F. Stoddart, Chem. Aust. 1992, 576. J. F. Stoddart, Acc. Chem. Research 2001, 34, 410.
7. V. Balzani, M. Gómez-Lopez, J. F. Stoddart, Acc. Chem. Research 1998, 31, 405. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3349. B. L. Feringa, Acc. Chem. Research 2001, 34, 504. J. F. Stoddart, Chem. Aust. 1992, 576. J. F. Stoddart, Acc. Chem. Research 2001, 34, 410.
8. V. Balzani, M. Gómez-Lopez, J. F. Stoddart, Acc. Chem. Research 1998, 31, 405. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3349. B. L. Feringa, Acc. Chem. Research 2001, 34, 504. J. F. Stoddart, Chem. Aust. 1992, 576. J. F. Stoddart, Acc. Chem. Research 2001, 34, 410.
9. J.-P. Sauvage, Acc. Chem. Research 1998, 31, 611.
10. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
11. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
12. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
13. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
14. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
15. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
16. P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M.-V. Martinez-Diaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 2000, 122, 3542. P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, New J. Chem. 1999, 23, 587. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. M. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 333. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344. Z.-T Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624. D. J. Cárdenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980.
17. D. B. Amabilino, J.-P. Sauvage, New J. Chem. 1998, 395. M. Linke, N. Fujita, J. C. Chambron, V. Heitz, J. P. Sauvage, New J. Chem. 2001, 25, 790. J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233. D. B. Amabilino, J.-P. Sauvage, Chem. Commun. 1996, 2441. M. J. Gunter, S. M. Farquhar, Org. Biomol. Chem. 2003, 1, 3450.
18. D. B. Amabilino, J.-P. Sauvage, New J. Chem. 1998, 395. M. Linke, N. Fujita, J. C. Chambron, V. Heitz, J. P. Sauvage, New J. Chem. 2001, 25, 790. J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233. D. B. Amabilino, J.-P. Sauvage, Chem. Commun. 1996, 2441. M. J. Gunter, S. M. Farquhar, Org. Biomol. Chem. 2003, 1, 3450.
19. D. B. Amabilino, J.-P. Sauvage, New J. Chem. 1998, 395. M. Linke, N. Fujita, J. C. Chambron, V. Heitz, J. P. Sauvage, New J. Chem. 2001, 25, 790. J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233. D. B. Amabilino, J.-P. Sauvage, Chem. Commun. 1996, 2441. M. J. Gunter, S. M. Farquhar, Org. Biomol. Chem. 2003, 1, 3450.
20. D. B. Amabilino, J.-P. Sauvage, New J. Chem. 1998, 395. M. Linke, N. Fujita, J. C. Chambron, V. Heitz, J. P. Sauvage, New J. Chem. 2001, 25, 790. J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233. D. B. Amabilino, J.-P. Sauvage, Chem. Commun. 1996, 2441. M. J. Gunter, S. M. Farquhar, Org. Biomol. Chem. 2003, 1, 3450.
21. D. B. Amabilino, J.-P. Sauvage, New J. Chem. 1998, 395. M. Linke, N. Fujita, J. C. Chambron, V. Heitz, J. P. Sauvage, New J. Chem. 2001, 25, 790. J.-C. Chambron, C. O. Dietrich-Buchecker, V. Heitz, J.-F. Nierengarten, J.-P. Sauvage, C. Pascard, J. Guilhem, Pure Appl. Chem. 1995, 67, 233. D. B. Amabilino, J.-P. Sauvage, Chem. Commun. 1996, 2441. M. J. Gunter, S. M. Farquhar, Org. Biomol. Chem. 2003, 1, 3450.
22. L. Flamigni, A. M. Talarico, S. Serroni, F. Puntoriero, M. J. Gunter, M. R. Johnston, T. P. Jeynes, Chem. Eur J. 2003, 9, 2649.
23. M. J. Gunter, M. R. Johnston, J. Chem. Soc., Chem. Commun. 1992, 1163.
24. M. J. Gunter, D. C. R. Hockless, M. R. Johnston, B. W. Skelton, A. H. White, J. Am. Chem. Soc 1994, 116, 4810.
25. M. J. Gunter, M. R. Johnston, J. Chem. Soc, Chem. Commun. 1994, 829.
26. M. J. Gunter, R. N. Warrener, Chem. Aust. 1997, 25.
27. I. Willner, E. Kaganer, E. Joselevich, H. Durr, E. David, M. J. Gunter, M. R. Johnston, Coord. Chem. Rev. 1998, 171, 261.
28. L. Flamigni, A. M. Talarico, M. J. Gunter, M. R. Johnston, T. P. Jeynes, New J. Chem. 2003, 27, 551.
29. M. J. Gunter, T. P. Jeynes, M. R. Johnston, P. Turner, Z. P. Chen, J. Chem. Soc., Perkin Trans. 2 1998, 21, 1945.
30. 3 was added to the reaction to aid in the formation of the this large macrocycle by a cation templating effect, the so called "cesium effect", see: G. Dijkstra, W. H. Kruizinga, R. M. Kellogg, J. Org. Chem. 1987, 52, 4230. The modification of Maruyama's procedure (A. Osuka, F. Kobayashi, K. Maruyama, Bull. Chem. Soc. Jpn. 1991, 64, 1213. A. Osuka, T. Nagata, F. Kobayashi, K. Maruyama, J. Heterocycl. Chem. 1990, 27, 1657) that was used for some previous related porphyrin synthesis was unsuccessful in this case.
31. 3 was added to the reaction to aid in the formation of the this large macrocycle by a cation templating effect, the so called "cesium effect", see: G. Dijkstra, W. H. Kruizinga, R. M. Kellogg, J. Org. Chem. 1987, 52, 4230. The modification of Maruyama's procedure (A. Osuka, F. Kobayashi, K. Maruyama, Bull. Chem. Soc. Jpn. 1991, 64, 1213. A. Osuka, T. Nagata, F. Kobayashi, K. Maruyama, J. Heterocycl. Chem. 1990, 27, 1657) that was used for some previous related porphyrin synthesis was unsuccessful in this case.
32. 3 was added to the reaction to aid in the formation of the this large macrocycle by a cation templating effect, the so called "cesium effect", see: G. Dijkstra, W. H. Kruizinga, R. M. Kellogg, J. Org. Chem. 1987, 52, 4230. The modification of Maruyama's procedure (A. Osuka, F. Kobayashi, K. Maruyama, Bull. Chem. Soc. Jpn. 1991, 64, 1213. A. Osuka, T. Nagata, F. Kobayashi, K. Maruyama, J. Heterocycl. Chem. 1990, 27, 1657) that was used for some previous related porphyrin synthesis was unsuccessful in this case.
33. M. J. Gunter, S. M. Farquhar, T. P. Jeynes, Org Biomol. Chem. 2003, 1, 4097.
34. J. E. Redman, J. K. M. Sanders, Org. Lett. 2000, 2, 4141.
35. Conformational interchange can occur by rotation around the C-C and C-O bonds in the strap, and not around the meso-C to phenyl bond; rotation around this bond is restricted and interconverts the two atropisomeric 6 and 7, or 8 and 9.
36. C. K. Johnson, ORTEP: ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
37. PLATON, A Multipurpose Crystallographic Tool, 1998, Utrecht University, Utrecht, The Netherlands. A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, C34.
38. PLATON, A Multipurpose Crystallographic Tool, 1998, Utrecht University, Utrecht, The Netherlands. A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, C34.
39. Some DMSO was found necessary to improve the solubility of 7b which otherwise tended to crystallize during the course of the NMR titration experiment. For consistency, the association constants of the other porphyrin receptors were also determined in this solvent.
40. A table of chemical shift changes and detailed rationale for the indicated structures of the complexes is given in the Supplementary Data.
41. M. J. Gunter, M. R. Johnston, B. W. Skelton, A. H. White, J. Chem. Soc, Perkin Trans. 1 1994, 1009. M. J. Gunter, M. R. Johnston, J. Chem. Soc., Perkin Trans. 1 1994, 995.
42. M. J. Gunter, M. R. Johnston, B. W. Skelton, A. H. White, J. Chem. Soc, Perkin Trans. 1 1994, 1009. M. J. Gunter, M. R. Johnston, J. Chem. Soc., Perkin Trans. 1 1994, 995.
43. A modification of the originally reported workup procedure was found necessary to remove the unchanged cyclophane components or the tetracationic cyclophane which proved difficult to separate from the desired catenane product by chromatography alone. This involved washing the reaction residue with hot water, followed by subsequent chromatography and anion exchange.
44. D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godinez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 1271. D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Cordova, L. A. 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.
45. D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godinez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 1271. D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Cordova, L. A. 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.
46. H. Ryeng, A. Ghosh, J. Am. Chem. Soc. 2002, 124, 8099. A. B. Parusel, T. Wondimagegn, A. Ghosh, J. Am. Chem. Soc. 2000, 122, 6371.
47. H. Ryeng, A. Ghosh, J. Am. Chem. Soc. 2002, 124, 8099. A. B. Parusel, T. Wondimagegn, A. Ghosh, J. Am. Chem. Soc. 2000, 122, 6371.
48. S. G. DiMagno, A. K. Wertsching, I. Charles, R. Ross, J. Am. Chem. Soc. 1995, 117, 8279. A. K. Wertsching, A. S. Koch, S. G. DiMagno, J. Am. Chem. Soc. 2001, 123, 3932.
49. S. G. DiMagno, A. K. Wertsching, I. Charles, R. Ross, J. Am. Chem. Soc. 1995, 117, 8279. A. K. Wertsching, A. S. Koch, S. G. DiMagno, J. Am. Chem. Soc. 2001, 123, 3932.
50. P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, K. R. Dress, E. Ishow, C. J. Kleverlaan, O. Kocian, J. A. Preece, N. Spencer, J. F. Stoddart, M. Venturi, S. Wenger, Chem. Eur J. 2000, 6, 3558. R. Ballardini, V. Balzani, M. T. Gandolfi, L. Prodi, M. Venturi, D. Philp, H. G. Ricketts, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1993, 32, 1301. Y.-Z. Hu, S. H. Bossmann, D. van Loyen, O. Schwarz, H. Dürr, Chem. Eur. J. 1999, 5, 1267.
51. P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, K. R. Dress, E. Ishow, C. J. Kleverlaan, O. Kocian, J. A. Preece, N. Spencer, J. F. Stoddart, M. Venturi, S. Wenger, Chem. Eur J. 2000, 6, 3558. R. Ballardini, V. Balzani, M. T. Gandolfi, L. Prodi, M. Venturi, D. Philp, H. G. Ricketts, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1993, 32, 1301. Y.-Z. Hu, S. H. Bossmann, D. van Loyen, O. Schwarz, H. Dürr, Chem. Eur. J. 1999, 5, 1267.
52. P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, K. R. Dress, E. Ishow, C. J. Kleverlaan, O. Kocian, J. A. Preece, N. Spencer, J. F. Stoddart, M. Venturi, S. Wenger, Chem. Eur J. 2000, 6, 3558. R. Ballardini, V. Balzani, M. T. Gandolfi, L. Prodi, M. Venturi, D. Philp, H. G. Ricketts, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1993, 32, 1301. Y.-Z. Hu, S. H. Bossmann, D. van Loyen, O. Schwarz, H. Dürr, Chem. Eur. J. 1999, 5, 1267.
53. 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.
54. G. M. Sheldrick, SHELXL-97. Program for crystal structure refinement. University of Göttingen, Germany, 1997.
55. teXsan for Windows and UNIX; Single Crystal Structure Analysis Software (1985-1999), MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
56. L. J. Farrugia, Appl. Cryst. 1999, 32, 837.
57. Xtal3.6 System (Eds.: S. R. Hall, D. J. du Boulay, R. Olthof-Hazekamp), University of Western Australia, 1999.
58. G. M. Sheldrick, SADABS. Empirical absorption correction program for area detector data., University of Gottingen, Germany, 1996. R. H. Blessing, Acta Crystallogr, Sect. A 1995, 51, 33.
59. G. M. Sheldrick, SADABS. Empirical absorption correction program for area detector data., University of Gottingen, Germany, 1996. R. H. Blessing, Acta Crystallogr, Sect. A 1995, 51, 33.
60. Bruker, XShell, Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA., 2000. Bruker, SMART, SAINT and XPREP. Area detector control and data integration and reduction software., Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA, 1995.
61. A. Altomare, M. Cascarano, C. Giacovazzo, C. Giaeovazzo, A. J. Guagliardi, Appl. Cryst. 1993, 26, 343.
62. G. M. Sheldrick, in Crystallographic Computing 3 (Ed.: C. K. a. R. G. G. M. Sheldrick), Oxford University Press, Oxford UK, 1985, pp. 175.