Counterion-induced translational isomerism in a bistable [2]rotaxane

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4167-4170

  Laursen, Bo W ^a   Nygaard, Sune ^a,b   Jeppesen, Jan O ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ACETONITRILE; ROTAXANE;

ARTICLE; ISOMERISM; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY;

EID: 9444228198     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048518l     Document Type: Article

References (38)

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20. 4+ switches. We therefore investigated the redox chemistry of Me4N-TRISPHAT in MeCN solution by cyclic voltammetry and found that this salt is not redox active in the range from -2 to +1.7 V vs SCE using ferrocene/ferrocenium as the internal standard.
21. Schill, G.; Rissler, K.; Fritz, H.; Vetter, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 187-189.
22. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
23. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
24. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
25. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
26. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
27. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
28. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
29. Several other examples of translational isomerism, in both bistable catananes and rotaxanes, induced by an environmental change such as solvent and temperature have been reported. See: (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. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093. (e) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (f) See ref 1c. (g) See ref 1e. (h) Bottari, G.; Dehez, F.; Leigh, D. A.; Nash, P. J.; Pérez, E. M.; Wong, J. K. Y.; Zerbetto, F. Angew. Chem., Int. Ed. 2003, 42, 5886-5889.
30. The influence of solvation on the conformational isomerism of calix-[4]arene and p-tert-butylcalix[4]arene has also been reported. See, for example: (a) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (b) Cajan, M.; Lhotak, P.; Lang, J.; Dvorakova, H.; Stibor, I.; Koca, J. J. Chem. Soc., Perkin Trans. 2 2002, 11, 1922-1929. (c) Alemán, C.; den Otter, W. K.; Tolpekina, T. V.; Briels, W. J. J. Org. Chem. 2004, 69, 951-958.
31. The influence of solvation on the conformational isomerism of calix-[4]arene and p-tert-butylcalix[4]arene has also been reported. See, for example: (a) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (b) Cajan, M.; Lhotak, P.; Lang, J.; Dvorakova, H.; Stibor, I.; Koca, J. J. Chem. Soc., Perkin Trans. 2 2002, 11, 1922-1929. (c) Alemán, C.; den Otter, W. K.; Tolpekina, T. V.; Briels, W. J. J. Org. Chem. 2004, 69, 951-958.
32. The influence of solvation on the conformational isomerism of calix-[4]arene and p-tert-butylcalix[4]arene has also been reported. See, for example: (a) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (b) Cajan, M.; Lhotak, P.; Lang, J.; Dvorakova, H.; Stibor, I.; Koca, J. J. Chem. Soc., Perkin Trans. 2 2002, 11, 1922-1929. (c) Alemán, C.; den Otter, W. K.; Tolpekina, T. V.; Briels, W. J. J. Org. Chem. 2004, 69, 951-958.
33. 3. See: Freitas, M. P.; Tormena, C. F.; Garcia, J. C.; Rittner, R.; Abraham, R. J.; Basso, E. A.; Santos, F. P.; Cedran, J. C. J. Phys. Org. Chem. 2003, 16, 833-838.
34. Only one previous example of anion-induced translational isomerism in a [2]rotaxane has been reported. See: Keaveney, C. M.; Leigh, D. Angew. Chem., Int. Ed. 2004, 43, 1222-1224.
35. + ions have been used to control the distribution of translational isomers in a neutral bistable [2]rotaxane. See: Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J. K. M.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 9884-9885.
36. Flood, A. H.; Ramirez, R. J A.; Deng, W.-Q.; Muller, R. P.; Goddard, W. A. III; Stoddart, J. F. Aust. J. Chem. 2004, 57, 301-322.
37. (a) Tseng, H.-R.; Steuerman, D. W.; Peters, A. J.; Flood, A. H.; Jeppesen J. O.; Nielsen, K. A.; Heath, J. R.; Stoddart, J. F. Angew. Chem., Int. Ed. In press.
38. (b) Flood, A. H.; Peters, A. J.; Vignon, S. A.; Steuerman, D. W.; Tseng, H.-R.; Heath, J. R.; Stoddart, J. F. Chem.-Eur. J. In press.