Skip to content
Publicly Available Published by De Gruyter January 1, 2009

Amide-based molecular shuttles (2001-2006)

  • José Berná , Giovanni Bottari , David A. Leigh and Emilio M. Pérez

Stimuli-responsive molecular shuttles are rotaxanes in which the macrocycle can be translocated from one position on the thread to a second site in response to an external trigger. Here, we present a brief overview of the contributions of the Leigh group to the field from 2001 to 2006. In this short period of time, molecular shuttles have moved from little more than laboratory curiosities to truly functional molecular machines.

References

1. Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology, J.-P. Sauvage, C. O. Dietrich-Buchecker (Eds.), Wiley-VCH, Weinheim (1999).Search in Google Scholar

2. doi:10.1119/1.10903, E. M. Purcell. Am. J. Phys. 45, 3 (1977).Search in Google Scholar

3. doi:10.1126/science.276.5314.917, R. D. Astumian. Science 276, 917 (1997).Search in Google Scholar

4. doi:10.1002/352760572X.ch7, E. R. Kay, D. A. Leigh. In Functional Artificial Receptors, A. D. Schrader, A. D. Hamilton (Eds.), pp. 333–406, Wiley-VCH, Weinheim (2005).Search in Google Scholar

5. doi:10.1021/ja00013a096, P. L. Anelli, N. Spencer, J. F. Stoddart. J. Am. Chem. Soc. 113, 5131 (1991).Search in Google Scholar

6. doi:10.1038/369133a0, R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart. Nature 369, 133 (1994).Search in Google Scholar

7. doi:10.1021/ja982167m, P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Gómez-López, M. V. Mart'nez-D'az, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams. J. Am. Chem. Soc. 120, 11932 (1998).Search in Google Scholar

8. doi:10.1002/anie.199314591, A. C. Benniston, A. Harriman. Angew. Chem., Int. Ed. 32, 1459 (1993).Search in Google Scholar

9. doi:10.1021/ja971438a, H. Murakami, A. Kawabuchi, K. Kotoo, M. Kunitake, N. Nakashima. J. Am. Chem. Soc. 119, 7605 (1997).Search in Google Scholar

10. doi:10.1021/ja971224t, A. S. Lane, D. A. Leigh, A. Murphy. J. Am. Chem. Soc. 119, 11092 (1997).Search in Google Scholar

11. doi:10.1002/anie.199723311, C. Gong, H. W. Gibson. Angew. Chem., Int. Ed. 36, 2331 (1997).Search in Google Scholar

12. doi:10.1002/1521-3773(20000915)39:18<3284::AID-ANIE3284>3.0.CO;2-7, M. C. Jiménez, C. Dietrich-Buchecker, J.-P. Sauvage. Angew. Chem., Int. Ed. 39, 3284 (2000).Search in Google Scholar

13. doi:10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO;2-X, V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart. Angew. Chem., Int. Ed. 39, 3348 (2000).Search in Google Scholar

14. V. Balzani, A. Credi, M. Venturi. Pure Appl. Chem. 75, 541 (2003).Search in Google Scholar

15. doi:10.1126/science.1057886, A. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel. Science 291, 2124 (2001).Search in Google Scholar

16. doi:10.1021/ja0352552, A. Altieri, F. G. Gatti, E. R. Kay, D. A. Leigh, D. Martel, F. Paolucci, A. M. Z. Slawin, J. K. Y. Wong. J. Am. Chem. Soc. 125, 8644 (2003).Search in Google Scholar

17. doi:10.1021/ja015919c, G. W. H. Wurpel, A. M. Brouwer, I. H. M. van Stokkum, M. A. F. Morales, D. A. Leigh. J. Am. Chem. Soc. 123, 11327 (2001).Search in Google Scholar

18. doi:10.1016/0047-2670(86)85007-9, T. C. Werner, J. Rodgers. J. Photochem. 32, 59 (1986).Search in Google Scholar

19. doi:10.1021/ol0274110, T. Da Ros, D. M. Guldi, M. A. F. Morales, D. A. Leigh, M. Prato, R. Turco. Org. Lett. 5, 689 (2003).Search in Google Scholar

20. doi:10.1002/anie.200250745, A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto. Angew. Chem., Int. Ed. 42, 2296 (2003).Search in Google Scholar

21. doi:10.1073/pnas.0134757100, F. G. Gatti, S. León, J. K. Y. Wong, G. Bottari, A. Altieri, M. A. F. Morales, S. J. Teat, C. Frochot, D. A. Leigh, A. M. Brouwer, F. Zerbetto. Proc. Natl. Acad. Sci. USA 100, 10 (2003).Search in Google Scholar

22. doi:10.1002/anie.200352176, G. Bottari, F. Dehez, D. A. Leigh, P. J. Nash, E. M. Pérez, J. K. Y. Wong, F. Zerbetto. Angew. Chem., Int. Ed. 42, 5886 (2003).Search in Google Scholar

23. doi:10.1039/b412570c, D. A. Leigh, E. M. Pérez. Chem. Commun. 2262 (2004).Search in Google Scholar

24. doi:10.1002/anie.200353248, C. M. Keaveney, D. A. Leigh. Angew. Chem., Int. Ed. 43, 1222 (2004).Search in Google Scholar

25. doi:10.1039/cs9932200409, Y. Marcus. Chem. Soc. Rev. 22, 409 (1993).Search in Google Scholar

26. doi:10.1002/anie.200501761, D. S. Marlin, D. González Cabrera, D. A. Leigh, A. M. Z. Slawin. Angew. Chem., Int. Ed. 45, 77 (2006).Search in Google Scholar

27. doi:10.1002/anie.200502624, D. S. Marlin, D. González Cabrera, D. A. Leigh, A. M. Z. Slawin. Angew. Chem., Int. Ed. 45, 1385 (2006).Search in Google Scholar

28. doi:10.1002/anie.200353606, J. S. Hannam, S. M. Lacy, D. A. Leigh, C. G. Saiz, A. M. Z. Slawin, S. G. Stitchell. Angew. Chem., Int. Ed. 43, 3260 (2004).Search in Google Scholar

29. doi:10.1021/ja0484193, E. M. Pérez, D. T. F. Dryden, D. A. Leigh, G. Teobaldi, F. Zerbetto. J. Am. Chem. Soc. 126, 12210 (2004).Search in Google Scholar

30. doi:10.1021/ja036665t, G. Bottari, D. A. Leigh, E. M. Pérez. J. Am. Chem. Soc. 125, 13360 (2003).Search in Google Scholar

31. doi:10.1021/cr9900228, B. L. Feringa, R. A. van Delden, N. Koumura, E. M. Geertsema. Chem. Rev. 100, 1789 (2000).Search in Google Scholar

32. doi:10.1021/ja057664z, M. N. Chatterjee, E. R. Kay, D. A. Leigh. J. Am. Chem. Soc. 128, 4058 (2006).Search in Google Scholar

33. Definitions of the terms “ratcheting”, “escapement”, “balance”, and “linkage” can be found in ref. 32.Search in Google Scholar

34. doi:10.1002/anie.200500101, D. A. Leigh, M. A. F. Morales, E. M. Pérez, J. K. Y. Wong, C. G. Saiz, A. M. Z. Slawin, A. J. Carmichael, D. M. Haddleton, A. M. Brouwer, W. J. Buma, G. W. H. Wurpel, S. León, F. Zerbetto. Angew. Chem., Int. Ed. 44, 3062 (2005).Search in Google Scholar

35. doi:10.1038/nmat1455, J. Berná, D. A. Leigh, M. Lubomska, S. M. Mendoza, E. M. Pérez, P. Rudolf, G. Teobaldi, F. Zerbetto. Nat. Mater. 4, 704 (2005).Search in Google Scholar

36. doi:10.1021/ol0344927, J. S. Hannam, T. J. Kidd, D. A. Leigh, A. J. Wilson. Org. Lett. 5, 1907 (2003).Search in Google Scholar

37. doi:10.1002/anie.200351458, T. J. Kidd, T. J. A. Loontjens, D. A. Leigh, J. K. Y. Wong. Angew. Chem., Int. Ed. 42, 3379 (2003).Search in Google Scholar

38. L. Hogg, D. A. Leigh, P. J. Lusby, A. Morelli, S. Parsons, J. K. Y. Wong. Angew. Chem., Int. Ed. 43, 1218 (2004).Search in Google Scholar

39. doi:10.1002/anie.200353622, A.-M. Fuller, D. A. Leigh, P. J. Lusby, I. D. H. Oswald, S. Parsons, D. B. Walker. Angew. Chem., Int. Ed. 43, 3914 (2004).Search in Google Scholar

40. doi:10.1021/ja057206q, V. Aucagne, D. A. Leigh, J. S. Lock, A. R. Thomson. J. Am. Chem. Soc. 128, 1784 (2006).Search in Google Scholar

41. doi:10.1021/ja056903f, V. Aucagne, K. D. Hänni, D. A. Leigh, P. J. Lusby, D. B. Walker. J. Am. Chem. Soc. 128, 2186 (2006).Search in Google Scholar

42. doi:10.1021/ja0159362, F. Biscarini, M. Cavallini, D. A. Leigh, S. León, S. J. Teat, J. K. Y. Wong, F. Zerbetto. J. Am. Chem. Soc. 124, 225 (2002).Search in Google Scholar

43. doi:10.1073/pnas.072695799, G. Brancato, F. Coutrot, D. A. Leigh, A. Murphy, J. K. Y. Wong, F. Zerbetto. Proc. Natl. Acad. Sci. USA 99, 4967 (2002).Search in Google Scholar

44. doi:10.1038/nature01758, D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto. Nature 424, 174 (2003).Search in Google Scholar

45. doi:10.1126/science.1103949, J. V. Hernández, E. R. Kay, D. A. Leigh. Science 306, 1532 (2004).Search in Google Scholar

Online erschienen: 2009-1-1
Erschienen im Druck: 2007-1-1

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 14.5.2024 from https://www.degruyter.com/document/doi/10.1351/pac200779010039/html
Scroll to top button