Intermittent molecular shuttle as a binary switch

Angewandte Chemie - International Edition

Volumn 43, Issue 16, 2004, Pages 2121-2124

  Jiang, Lasheng ^a   Okano, Junji ^a   Orita, Akihiro ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Chelation; Coordination modes; Copper; Molecular devices; Rotaxanes

Indexed keywords

COMPLEXATION; IONS; MOLECULES;

DECOMPLEXATION; INTERMITTENT MOLECULAR SHUTTLES;

ORGANIC COMPOUNDS;

ROTAXANE;

ARTICLE; COMPLEX FORMATION; EVAPORATION; HEATING; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PH MEASUREMENT; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

EID: 4544229158     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353534     Document Type: Article

References (21)

1. a) Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001;
2. b) "Molecuar Machines and Motors": Structure and Bonding, Vol. 99 (Ed.: J.-P. Sauvage), Springer, Berlin, 2001;
3. c) special issue on "Molecular Machines", Acc. Chem. Res. 2001, 6;
4. d) V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines, Wiley-VCH, Weinheim, 2003.
5. a) V. Balzani, M. Gómez-López, J. F. Stoddart, Acc. Chem. Res. 1998, 31, 405;
6. b) J. O. Jeppesen, K. A. Nielsen, J. Perkins, S. A. Vignon, A. D. Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. Becher, J. F. Stoddart, Chem. Eur. J. 2003, 9, 2982;
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8. A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092.
9. A nondegenerate [2]rotaxane reported by Stoddart and co-workers may be taken as a quasi-dynamic/static switch: A bead was fixed on one of the stations by oxidation or treatment with acid and the shuttling process recovered by reduction or treatment with base. However, because of the preferential interaction of the bead with one of the nonequivalent stations over the other, the shuttling in this case is not completely free but biased, and, hence, this system is not suitable for an all-or-nothing switch: R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133. A similar situation was reported for a catenane: P. Ashton, P. R. Ballardini, V. Balzani, A. Credi, M. T. Gondolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Ventura, A. J. P. White, D. J. Williams, J. Am. Chem. Soc 1995, 117, 11171. Another example of the interruption of the shuttling process was reported for a glycylglycine rotaxane: A bead was trapped through formation of hydrogen bonds in nonpolar solvents whereas shuttling occurred in polar solvents as a result of the destruction of the hydrogen-bonding interactions; however, such a solvent change is not practical: D. A. Leigh, A. Murphy, M. J. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752; Angew. Chem. Int. Ed. Engl. 1997, 36, 728.
10. A nondegenerate [2]rotaxane reported by Stoddart and co-workers may be taken as a quasi-dynamic/static switch: A bead was fixed on one of the stations by oxidation or treatment with acid and the shuttling process recovered by reduction or treatment with base. However, because of the preferential interaction of the bead with one of the nonequivalent stations over the other, the shuttling in this case is not completely free but biased, and, hence, this system is not suitable for an all-or-nothing switch: R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133. A similar situation was reported for a catenane: P. Ashton, P. R. Ballardini, V. Balzani, A. Credi, M. T. Gondolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Ventura, A. J. P. White, D. J. Williams, J. Am. Chem. Soc 1995, 117, 11171. Another example of the interruption of the shuttling process was reported for a glycylglycine rotaxane: A bead was trapped through formation of hydrogen bonds in nonpolar solvents whereas shuttling occurred in polar solvents as a result of the destruction of the hydrogen-bonding interactions; however, such a solvent change is not practical: D. A. Leigh, A. Murphy, M. J. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752; Angew. Chem. Int. Ed. Engl. 1997, 36, 728.
11. A nondegenerate [2]rotaxane reported by Stoddart and co-workers may be taken as a quasi-dynamic/static switch: A bead was fixed on one of the stations by oxidation or treatment with acid and the shuttling process recovered by reduction or treatment with base. However, because of the preferential interaction of the bead with one of the nonequivalent stations over the other, the shuttling in this case is not completely free but biased, and, hence, this system is not suitable for an all-or-nothing switch: R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133. A similar situation was reported for a catenane: P. Ashton, P. R. Ballardini, V. Balzani, A. Credi, M. T. Gondolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Ventura, A. J. P. White, D. J. Williams, J. Am. Chem. Soc 1995, 117, 11171. Another example of the interruption of the shuttling process was reported for a glycylglycine rotaxane: A bead was trapped through formation of hydrogen bonds in nonpolar solvents whereas shuttling occurred in polar solvents as a result of the destruction of the hydrogen-bonding interactions; however, such a solvent change is not practical: D. A. Leigh, A. Murphy, M. J. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752; Angew. Chem. Int. Ed. Engl. 1997, 36, 728.
12. A nondegenerate [2]rotaxane reported by Stoddart and co-workers may be taken as a quasi-dynamic/static switch: A bead was fixed on one of the stations by oxidation or treatment with acid and the shuttling process recovered by reduction or treatment with base. However, because of the preferential interaction of the bead with one of the nonequivalent stations over the other, the shuttling in this case is not completely free but biased, and, hence, this system is not suitable for an all-or-nothing switch: R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133. A similar situation was reported for a catenane: P. Ashton, P. R. Ballardini, V. Balzani, A. Credi, M. T. Gondolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Ventura, A. J. P. White, D. J. Williams, J. Am. Chem. Soc 1995, 117, 11171. Another example of the interruption of the shuttling process was reported for a glycylglycine rotaxane: A bead was trapped through formation of hydrogen bonds in nonpolar solvents whereas shuttling occurred in polar solvents as a result of the destruction of the hydrogen-bonding interactions; however, such a solvent change is not practical: D. A. Leigh, A. Murphy, M. J. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752; Angew. Chem. Int. Ed. Engl. 1997, 36, 728.
13. E. W. Wong, C. P. Collier, M. Belohradsky, F. M. Raymo, J. F. Stoddart, J. R. Heath, J. Am. Chem. Soc. 2000, 122, 5831.
14. For detailed information, see the Supporting Information.
15. 1 salt. The choice of the solvent is crucial for the formation of the complex; only acetone and acetonitrile can be used, as the complex does not form in other solvents.
16. For rotaxanes dimerized through complexation with a copper ion at their wheel peripheries, see X.-y. Li, J. Illigen, M. Nieger, S. Michel, C. A. Schalley, Chem. Eur. J. 2003, 9, 1332.
17. Available form Muromachi Technos Co., Tokyo.
18. A 2.5 N solution of HCl (0.2 mL) was added to a suspension of the resin (5.0 g) in water (15 mL). The mixture was stirred for 14 h and then the resin filtered off and dried. The resin thus obtained had a pH value of 5.5.
19. A 1:1 complex was formed even in the presence of excess 1c.
20. To facilitate the filtration a small amount of argon was removed from the lower compartment by syringe while the upper compartment was pressurized with an argon balloon.
21. In this case, the pH value of the resin should be adjusted to 5.0. Above this value, the rotaxane returned to 2b and a small amount of 3 (ca. 6%).