Entropy-Driven Translational Isomerism: A Tristable Molecular Shuttle

Angewandte Chemie - International Edition

Volumn 42, Issue 47, 2003, Pages 5886-5889

  Bottari, Giovanni ^a   Dehez, Francois ^b   Leigh, David A ^a   Nash, Phillip J ^a   Pérez, Emilio M ^a   Wong, Jenny K Y ^a   Zerbetto, Francesco ^b  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Entropy; Macrocycles; Molecular devices; Photochemistry; Rotaxanes

Indexed keywords

CONFORMATIONS; ENTROPY; PHOTOCHEMICAL REACTIONS;

MOLECULAR SHUTTLE;

ISOMERS;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONFORMATION; ENTHALPY; ENTROPY; HYDROGEN BOND; ISOMERISM; ISOMERIZATION; MOLECULAR STABILITY; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE DEPENDENCE;

EID: 0346789524     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352176     Document Type: Article

References (35)

1. a) Molecular Catenanes, Rotaxanes and Knots (Ed.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999;
2. b) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3483-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
3. b) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3483-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
4. c) Special issue on Molecular Machines: Acc. Chem. Res. 2001, 34, 409-522;
5. d) M. Venturi, A. Credi, V. Balzani, Molecular Devices and Machines - A Journey into the Nanoworld, Wiley-VCH, Weinheim, 2003.
6. Exceptions are environment-sensitive shuttles where the preferred position of the macrocycle is determined by the differing solvation of the binding sites in various solvent systems. a) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093;
7. b) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428;
8. c) Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333;
9. 6]DMSO.
10. binding of the macrocycle for the two stations in the chemically transformed shuttle.
11. a) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137;
12. b) P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Gómez-López, M.-V. Martí nez-Díaz, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942;
13. c) J. W. Lee, K. Kim, K. Kim, Chem. Commun. 2001, 1042-1043;
14. d) A. M. Elizarov, S.-H. Chiu, J. F. Stoddart, J. Org. Chem. 2002, 67, 9175-9181.
15. a) H. Murakami, A. Kawabuchi, K. Kotoo, M. Kunitake, N. Nakashima, J. Am. Chem. Soc. 1997, 119, 7605-7606;
16. b) N. Armaroli, V. Balzani, J. P. Collin, P. Gaviñia, J. P. Sauvage, B. Ventura, J. Am. Chem. Soc. 1999, 121, 4397-4408;
17. c) 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, 3558-3574;
18. d) A. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel, Science 2001, 291, 2124-2128;
19. e) G. W. H. Wurpel, A. M. Brouwer, I. H. M. van Stokkum, A. Farran, D. A. Leigh, J. Am. Chem. Soc. 2001, 123, 11327-11328;
20. f) C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847-1850; Angew. Chem. Int. Ed. 2002, 41, 1769-1772;
21. f) C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2002, 114, 1847-1850; Angew. Chem. Int. Ed. 2002, 41, 1769-1772;
22. g) A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto, Angew. Chem. 2003, 115, 2398-2402; Angew. Chem. Int. Ed. 2003, 42, 2296-2300.
23. g) A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto, Angew. Chem. 2003, 115, 2398-2402; Angew. Chem. Int. Ed. 2003, 42, 2296-2300.
24. a) P.-L. Anelli, M. Asakawa, P.R. Ashton, R. A. Bissell, G. Clavier, R. Górski, A. E. Kaifer, S. J. Langford, G. Mattersteig, S. Menzer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, Chem. Eur. J. 1997, 3, 1113-1135;
25. b) J.-P. Collin, P. Gaviñia, J.-P. Sauvage, New J. Chem. 1997, 21, 525-528;
26. c) N. Armaroli, V. Balzani, J.-P. Collin, P. Gaviñia, J.-P. Sauvage, B. Ventura, J. Am. Chem. Soc. 1999, 121, 4397-4408;
27. d) R. Ballardini, V. Balzani, W. Dehaen, A. E. Dell'Erba, F. M. Raymo, J. F. Stoddart, M. Venturi, Eur. J. Org. Chem. 2000, 591-602;
28. e) C. P. Collier, J. O. Jeppesen, Y. Luo, J. Perkins, E. W. Wong, J. R. Heath, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 12632-12641.
29. [5g] For a [2]rotaxane where a temperature increase is used to overcome a significant kinetic barrier to shuttling following a chemical change, see ref [4c]. A bistable [2]rotaxane that appears to undergo translational isomerism as a result of differences in the entropy of solvation of two stations has recently been reported (J. O. Jeppesen, K. A. Nielsen, J. Perkins, S. A. Vignon, A. Di Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. Becher, J. F. Stoddart, Chem. Eur. J. 2003, 9, 2982-3007).
30. A series of interesting theoretical designs for entropy-driven mechanical motion in mechanically interlocked molecules have recently been suggested (A. Hanke, R. Metzler, Chem. Phys. Lett. 2002, 359, 22-26).
31. For other types of tristable switch see a) (supramolecular) P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 3951-3957;
32. b) (molecular) F. M. Raymo, S. Giordani, A. J. P. White, D. J. Williams, J. Org. Chem. 2003, 68, 4158-4169;
33. c) ([2]- and [3]catenanes) D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 2003, 424, 174-179.
34. At 308 K the ratio of succ-Z-1:dodec-Z-1 is ∼ 90:10; at 258 K it is ∼ 15:85.
35. F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989.