A donor-acceptor substituted molecular motor: Unidirectional rotation driven by visible light

Organic and Biomolecular Chemistry

Volumn 1, Issue 1, 2003, Pages 33-35

  Van Delden, Richard A ^a   Koumura, Nagatoshi ^a   Schoevaars, Annemarie ^a   Meetsma, Auke ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; DESULFURIZATION; GIBBS FREE ENERGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

CIRCULAR DICHROISM; DIASTEREOISOMERS; DONOR-ACCEPTOR SUBSTITUTED MOLECULAR MOTOR; PHOTOPHYSICAL PROPERTIES; PROTONATION; X-RAY CRYSTAL STRUCTURE;

OLEFINS;

EID: 0041322819     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209378b     Document Type: Article

References (30)

1. (a) Sci. Amer., special issue: Nanotech: Th Science of Small Gets Down to Business, September 2001
2. (b) R.P. Feynman in Miniaturization, ed. H. D. Gilbert, New York. 1971
3. (c) K. E. Drexler, Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York
4. (a) B. L. Feringa, R. A. van Delden, N. Koumura and E. M. Geertsema, Chem. Rev., 2000, 100, 1789-1816
5. (b) Molecular Switches, ed. B.L. Feringa, Wiley, Weinheim, 2001.
6. T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. Garcia, F. R. Lang, M. H. Kim and M. P. Jette, J. Am. Chem. Soc., 1994, 116, 3657-3658.
7. A. M. Stevens and C. J. Richards, Tetrahedron Lett., 1997, 38, 7805-7808
8. (b) J. Clayden and J. H. Pink, Angew. Chem. Int. Ed. Engl., 1998, 37, 1937-1939.
9. T. C. Bedard and J. S. Moore, J. Am. Chem. Soc., 1995, 117, 10662-10671
10. M. C. Jimenénez, C. Dietrich-Buchecker and J.-P. Sauvage, Angew. Chem., Int. Ed., 2000, 39, 3284-3287.
11. B. L. Feringa, N. Koumura, R. A. van Delden and M. K. J. ter Wiel, Appl. Phys. A, 2002, 75, 301-308.
12. (a) J. P. Abrahams, A. G. W. Leslie, R. Lutter and J. E. Walker, Nature, 1994, 370, 621-628
13. (b) H. Noji, M. Yasuda and K. Kinosita Jr., Nature, 1997, 386, 299-302
14. (c) Special issue: Science, Movement: Molecular to Robotic, 2000, 288, 79-106.
15. V. Amendola, L. Fabbrizzi, C. Mangano and P. Pallavicini, Acc. Chem. Res., 2001, 34, 488-493.
16. (a) V. Balzani, A. Credi, M. Raymo and J. F. Stoddard, Angew. Chem., Int. Ed., 2000, 39, 3349-3391
17. (b) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier and J. R. Heath, Acc. Chem. Res., 2001, 34, 433-444
18. (c) R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi and M. Venturi, Acc. Chem. Res., 2001, 34, 445-455
19. (d) C. A. Schalley, K. Beizai and F. Vögtle, Acc. Chem. Res., 2001, 34, 465-476
20. (e) J.-P. Collin, C. Dietrich-Buchecker, P. Gaviña, M. C. Jiminez-Moleroa and J.-P. Sauvage, Acc. Chem. Res., 2001, 34, 477-487.
21. T. R. Kelly, H. De Silva and R. A. Silva, Nature, 1999, 401, 150-152.
22. N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada and B. L. Feringa, Nature, 1999, 401, 152-155.
23. N. Koumura, E. M. Geertsema, A. Meetsma and B. L. Feringa, J. Am. Chem. Soc., 2000, 122, 12005-12006.
24. N. Koumura, E. M. Geertsema, M. B. van Gelder, A. Meetsma and B. L. Feringa, J. Am. Chem. Soc., 2002, 124, 5037-5051.
25. W. F. Jager, J. C. de Jong, B. de Lange, N. P. M. Huck, A. Meetsma and B. L. Feringa, Angew. Chem.Int. Ed. Engl., 1995, 34, 348-350.
26. See supplementary material for details on synthesis, spectroscopic data and resolution.
27. o) criterion of observability. The absolute configuration of (cis)-1 could not be determined via X-ray methods.
28. b).
29. The monochromatic efficiency, considering the energy differences between the unstable and stable forms and the UV-Vis absorption of the isomers can be estimated to be about 0.6%.
30. N. P. M. Huck and B. L. Feringa, J. Chem. Soc., Chem. Commun., 1995, 1095-1096.