Chemistry: A reversible, unidirectional molecular rotary motor driven by chemical energy

Science

Volumn 310, Issue 5745, 2005, Pages 80-82

  Fletcher, Stephen P ^a   Dumur, Frédéric ^a   Pollard, Michael M ^a   Feringa, Ben L ^a  

^a Department of Organic and Molecular Inorganic Chemistry   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BROWNIAN MOVEMENT; CHEMICAL BONDS; MOLECULAR STRUCTURE;

CHEMICAL REAGENTS; CHEMICALLY DISTINCT REACTIONS;

MOLECULAR BIOLOGY;

LACTONE; MOLECULAR MOTOR; NAPHTHYL GROUP; PHENYL GROUP;

NANOTECHNOLOGY;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; ROTATION; THERMODYNAMICS;

STATOR;

EID: 26444588140     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1117090     Document Type: Article

References (39)

1. R. P. Feynman, in Miniaturization, H. D. Gilbert, Ed. (Reinhold, New York, 1961).
2. K. E. Drexler, Nanosystems: Molecular Machinery, Manufacturing and Computation (Wiley, New York, 1992).
3. K. Kinbara, T. Aida, Chem. Rev. 105, 1377 (2005).
4. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 39, 3349 (2000).
5. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines. A Journey into the Nano World (Wiley-VCH. Weinheim, Germany, 2003).
6. M. Schliwa, Ed., Molecular Motors (Wiley-VCH, Weinheim, Germany, 2002).
7. C. P. Mandl, B. König, Angew. Chem. Int. Ed. Engl. 43, 1622 (2004).
8. G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 105, 1281 (2005).
9. J. E. Walker, Angew. Chem. Int Ed. Engl. 37, 2308 (1998).
10. P. D, Boyer, Angew. Chem. Int. Ed. Engl. 37, 2296 (1998).
11. N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 401, 152 (1999).
12. N. Koumura, E. M. Geertsema, M. B. van Gelder, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 124, 5037 (2002).
13. M. K. J. ter Wiel, R. A. van Delden, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 125, 15076 (2003).
14. D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 424, 174 (2003).
15. J. V. Hernández, E. R. Kay, D. A. Leigh, Science 306, 1532 (2004).
16. A. M. Fennimore et al., Nature 424, 408 (2003).
17. K. Hoki, M. Yamaki, Y. Fujimura, Angew. Chem. Int. Ed. Engl. 42, 2976 (2003).
18. M. Yamaki, K. Hoki, Y. Ohtsuki, H. Kono, Y. Fujimara, J. Am. Chem. Soc. 127, 7300 (2005).
19. Z. C. Tu, X. Hu, Phys. Rev. B 72, 033404 (2005) (preprint available at http://arxiv.org/abs/cond-mat/0501062).
20. M. F. Hawthorne et al., Science 303, 1849 (2004).
21. B. J. Dahl, B. P. Branchaud, Tetrahedron Lett. 45, 9599 (2004).
22. T. R. Kelly, H. De Silva, R. A. Silva, Nature 401, 150 (1999).
23. T. R. Kelly, R. A. Silva, H. De Silva, S. Jasmin, Y. J. Zhao, J. Am. Chem. Soc. 122, 6935 (2000).
24. T. R. Kelly, I. Tellitu, J. P. Sestelo, Angew. Chem. Int. Ed. Engl. 36, 1866 (1997).
25. For a related system see R. P. Feynman, R. B. Leighton, M. Sands, The Feynman Lectures on Physics (Addison-Wesley, Reading, MA, 1963), voL 1, chap. 46.
26. A. P. Davis, Angew. Chem. Int. Ed. Engl. 37, 909 (1998).
27. C. Bustamante, D. Keller, C. Oster, Acc. Chem. Res. 34, 412 (2001).
28. H. Wang, C. Oster, Nature 396, 279 (1998).
29. C. Oster, H. Wang, Biochim. Biophys. Acta 482, 1458 (2000).
30. T. Elston, H. Wang, G. Oster, Nature 391, 510 (1998).
31. R. Astumian, Science 276, 917 (1997).
32. E. J. Corey, C. J. Helal, Angew. Chem. Int. Ed. Engl. 37, 1986 (1998).
33. G. Bringmann, T. Hartung, Angew. Chem. 104, 782 (1992),
34. Angew. Chem. Int. Ed. Engl. 31, 761 (1992).
35. G. Bringmann et al., J. Organomet. Chem 661, 31 (2002).
36. Materials and methods are available as supporting material on Science Online.
37. The configurational stability of the open forms was confirmed by chiral HPLC analysis, which showed no change in the enantiomeric ratio of the open forms throughout the chemical transformations.
38. The configurational stability of 1b and 1d was also verified by following its circular dichroism with respect to time. No change was observed after monitoring for 2 hours at 100°0C.
39. We thank the Netherlands Organization for Scientific Research (NWO-CW), the Natural Sciences and Engineering Research Council of Canada (NSERC) (a post-doctoral fellowship to S.P.F.), and the Materials Science Centre (a postdoctorat fellowship to M.M.P.) for financial support. We thank M. Walko for performing the molecular modeling calculations.