Net directed 180° aryl-aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8359-8362

  Lin, Ying ^a   Dahl, Bart J ^a   Branchaud, Bruce P ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Directed bond rotation; Molecular machines; Molecular motors

Indexed keywords

LACTONE DERIVATIVE; MOLECULAR MOTOR;

ARTICLE; CHEMICAL BOND; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LACTONIZATION; MASS SPECTROMETRY; RING OPENING; ROTATION; STEREOCHEMISTRY;

EID: 27644552145     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.151     Document Type: Article

References (37)

1. V. Balzani, A. Credi, and M. Venturi Molecular Devices and Machines 2003 Wiley-VCH Weinheim, Germany
2. V. Balzani, A. Credi, F.M. Raymo, and J.F. Stoddart Angew. Chem. 112 2000 3484
3. Angew. Chem., Int. Ed. 39 2000 3348
4. M. Schliwa Molecular Motors 2003 Wiley-VCH Weinheim, Germany
5. D.S. Goodsell Our Molecular Nature 1996 Copernicus New York, NY
6. C.P. Mandl, and B. König Angew. Chem. 2004 1650
7. Angew. Chem., Int. Ed. 116 2004 1622
8. Exclusive unidirectional rotation is therefore ideal, but not required.
9. N. Koumura, E.M. Geertsema, M.B. van Gelder, A. Meetsma, and B.L. Feringa J. Am. Chem. Soc. 124 2002 5037
10. R.V. van Delden, M.K.J. ter Wiel, H. de Jong, A. Meetsma, and B.L. Feringa Org. Biomol. Chem. 10 2004 1531
11. N. Koumura, R.W.J. Ziglistra, R.A. Van Delden, N. Harada, and B.L. Feringa Nature 401 1999 152
12. D.A. Leigh, J.K.Y. Wong, F. Dehez, and F. Zerbetto Nature 424 2003 174
13. J.V. Hernandez, E.R. Kay, and D.A. Leigh Science 306 2004 1532
14. T.R. Kelly, H. De Silva, and R.A. Silva Nature 401 1999 150
15. T.R. Kelly, R.A. Silva, H. De Silva, S. Jasmin, and Y. Zhao J. Am. Chem. Soc. 122 2000 6935
16. T.R. Kelly, and E.F. Merkert Acc. Chem. Res. 34 2001 514
17. H. Jian, and J.M. Tour J. Org. Chem. 68 2003 5091
18. D.C. Caskey, R.K. Shoemaker, and J. Michl Org. Lett. 6 2004 2093
19. X. Zheng, M.E. Mulcahy, D. Horinek, F. Galeotti, T.F. Magnera, and J. Michl J. Am. Chem. Soc. 126 2004 4540
20. A. Carella, G. Rapenne, and J.P. Launay New J. Chem. 29 2005 288
21. M. Yamaki, K. Hoki, Y. Ohtsuki, H. Kono, and Y. Fujimara J. Am. Chem. Soc. 127 2005 7300
22. M.F. Hawthorne, J.I. Zink, D. Neuhauser, J.M. Skelton, M.J. Bayer, C. Liu, E. Livshits, and R. Baer Science 303 2004 1849
23. B.J. Dahl, and B.P. Branchaud Tetrahedron Lett. 45 2004 9599
24. R.A. Van Delden, N. Koumara, N. Harada, and B.L. Feringa Proc. Nat. Acad. Sci. U.S.A. 99 2002 4945
25. Y. Tabe, and H. Yokoyama Nat. Mater. 2 2003 806
26. G. Bringmann, M. Breuning, S. Tasler, H. Endress, C.L.J. Ewers, L. Göbel, K. Peters, and E.-M. Peters Chem. Eur. J. 5 1999 3029
27. G. Bringmann, M. Breuning, R. Walter, A. Wuzik, K. Peters, and E.-M. Peters Eur. J. Org. Chem. 1999 3047
28. G. Bringmann, M. Breuning, and S. Tasler Synthesis 1999 525
29. G. Bringmann, and D. Menche Acc. Chem. Res. 34 2001 615
30. H. Pellissier Tetrahedron 59 2003 8291
31. M. Yoshida, M. Minabe, and K. Suzuki Bull. Chem. Soc. Jpn. 56 1983 2179
32. C. Graebe, and C. Aubin Liebigs Ann. Chem. 247 1988 257
33. G. Mehta, and P.N. Pandey Synthesis 1975 404
34. M. Caswell, and G.L. Schmir J. Am. Chem. Soc. 102 1980 4815
35. See Supplementary data for experimental details.
36. This characterization is useful for determining the specific direction of rotation but is unnecessary in verifying that net unidirectional 180°rotation has occurred.
37. Note that in a bulk molecular motor system this seemingly limited efficiency of the proposed system may be sufficient to statistically generate useful work and/or change the properties of the surrounding environment.