Controlling molecular rotary motion with a self-complexing lock

Angewandte Chemie - International Edition

Volumn 49, Issue 6, 2010, Pages 1107-1110

  Qu, Da Hui ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Molecular devices; Molecular motors; Photochemistry; Protonation; Self complexation

Indexed keywords

ACID BASE; AMMONIUM IONS; MACROCYCLES; MOLECULAR DEVICE; MOLECULAR MOTORS; PHOTOCHEMISTRY; POLAR SOLVENTS; ROTARY MOTIONS; ROTARY MOTOR;

AMMONIUM COMPOUNDS; LINEAR MOTORS; MOTORS; PROTONATION;

COMPLEXATION;

FLUORINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM;

FLUORINE COMPOUNDS; ISOMERISM; MOLECULAR STRUCTURE;

EID: 76249100833     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906064     Document Type: Article

References (52)

1. a) Molecular Motors (Ed.: M. Schliwa), Wiley-VCH, Weinheim, 2003;
2. b) V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld, WileyVCH, Weinheim, 2008;
3. c) Molecular Machines and Motors (Ed. : J.-P. Sauvage), Springer, New York, 2001.
4. For reviews, see: a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
5. Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
6. b) K. Kinbara, T. Aida, Chem. Rev. 2005, 105, 1377-1400;
7. c) G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281-1376;
8. d) H. Tian, Q.C. Wang, Chem. Soc. Rev. 2006, 35, 361-374;
9. e) W. R. Browne, B. L. Feringa, Nat. Nanotechnol 2006, 1, 25-35;
10. f) V. Balzani, A. Credi, S. Silvi, M. Venturi, Chem. Soc. Rev. 2006, 35,1135-1149;
11. g) S. Saha, J. F. Stoddart, Chem. Soc Rev. 2007, 36, 77-92;
12. h) B. Champin, P. Mobian, J.-P. Sauvage, Chem. Soc. Rev. 2007, 36, 358-366;
13. i) E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72-196;
14. Angew. Chem. Int. Ed. 2007, 46, 72-191;
15. j) M. G. L. van den Heuvel, C. Dekker, Science 2007, 317, 333-336;
16. k) B. L. Feringa, J. Org. Chem. 2007, 72, 6635-6652.
17. For other unidirectional molecular motors, see : a) T. R. Kelly, H. De Silva, R. A. Silva, Nature 1999, 401,150-152;
18. b) D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 2003, 424,174-179;
19. c) S. P. Fletcher, F. Dumur, M. M. Pollard, B. L. Feringa, Science 2005, 310, 80-82.
20. For examples, see: a) S. Shinkai, M. Ishihara, K. Ueda, O. Manabe, J. Chem Soc. Perkin Trans. 2 1985, 511-518;
21. b) P. R. Ashton, R. Ballardini, V Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D.J. Williams, Chem. Eur. J. 1997, 5, 152-170;
22. c) G. M. Whitesides, B. A. Grzybowski, Science 2002, 295, 2418-2421;
23. d) Y. Liu, A. H. Flood, J. F. Stoddart, J. Am. Chem. Soc 2004,126,9150-9151.
24. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J, Williams, Angew. Chem. 1995, 107, 1997-2001;
25. Angew. Chem. Int. Ed Engl. 1995, 34,1865-1869;
26. b) M.V. Martínez-Díaz, N. Spencer, J.F. Stoddart, Angew. Chem. 1997, 109, 1991-1994;
27. Angew. Chem. Int. Ed. Engl. 1997, 36,1904-1907.
28. a) P. R. Ashton, I. W. Baxter, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, R. Wolf, Angew. Chem. 1998, 110, 2016-2019;
29. Angew. Chem. Int. Ed. 1998, 37, 1913-1916;
30. b) N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520;
31. Angew. Chem. Int. Ed. 1998, 37, 2361-2364;
32. c) S. J. Cantrill, G J. Youn, J. F. Stoddart, D. J. Williams, J. Org. Chem. 2001, 66, 6857-6872;
33. d) F. Coutrot, C. Romuald, E. Busseron, Org. Lett. 2008, 10, 3741-3744.
34. For examples of lockable molecular devices, see: a) N. P. M. Huck, B. L. Feringa, J. Chem. Soc. Chem. Commun. 1995,1095 -1096;
35. b) Q.C. Wang, D.H. Qu, J. Ren, K. Chen, H. Tian, Angew. Chem. 2004, 116, 2715-2719;
36. Angew. Chem. Int. Ed. 2004, 43, 2661-2665;
37. c) D.H. Qu, F.Y. Ji, Q.C. Wang, H. Tian, Adv. Mater. 2006, 18, 2035-2038;
38. d) C. J. Richmond, A. D. C. Parenty, Y.F. Song, G Cooke, L. Cronin, J. Am. Chem. Soc 2008, 130,13059-13065.
39. For examples of first-generation molecular motors, see: a) N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 1999, 401, 152-155;
40. b) M. K. J. ter Wiel, R. A. van Delden, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 15076-15086.
41. For examples of second-generation molecular motors, see: a) N. Koumura, E. M. Geertsema, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 12005-12006;
42. b) N. Koumura, E. M. Geertsema, M. B. van Gelder, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 5037-5051;
43. c) J. Vicario, M. Walko, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 5127-5135;
44. d) M. Klok, N. Boyle, M. T. Pryce, A. Meetsma, W.R. Browne, B. L. Feringa, J. Am. Chem. Soc. 2008, 130, 10484-10485.
45. a) M. M. Pollard, M. Klok, D. Pijper, B. L. Feringa, Adv. Funct. Mater. 2007, 77, 718-729.
46. 1HNMR spectral data of stable and unstable isomers of motor 1.
47. Tributylamine, triethylamine, and diisopropylethylamine were also used to deprotonate the dialkylammonium ion, but the deprotonation was incomplete in each case, even, if a large excess of base was added.
48. -1), corresponding to a half-life of 77 s at room temperature. In this case, unstable isomers could not be observed at room temperature upon irradiation, owing to fast thermal helix inversion.
49. Under conditions in which no thermal isomerization occurred, a secondary, slower photochemical process was also observed in. which stable cis-1 isomerized directly to stable trans-1. Continued irradiation ultimately gave a photostationary state containing all three isomers of 1 in a 100:20:7 ratio of unstable trans/stable cis/unstable cis. Only trace amounts of stable trans-1 were observed, as it was converted into unstable cis-1 quantitatively upon irradiation; for an extensive analysis of competing processes in molecular motors, see, for example, E. M. Geertsema, S. J. van de Molen, M. Martens, B. L. Feringa, Proc Natl. Acad. Sci. USA 2009, 106,16919-16924.
50. D. Pijper, R. A. van Delden, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 17612-17613.
51. 2, which can produce trace amounts of HCl that effect the isomerization at very low concentration. Addition of base can neutralize the traces of acid and promote the photochemical conversion.
52. The presence of an ammonium group does not interfere with the photochemistry.