A light-gated STOP-GO molecular shuttle

Journal of the American Chemical Society

Volumn 131, Issue 7, 2009, Pages 2493-2495

  Coskun, Ali ^a   Friedman, Douglas C ^a   Li, Hao ^a   Patel, Kaushik ^a   Khatib, Hussam A ^a   Stoddart, J Fraser ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATIC BARRIERS; EQUILIBRIUM DYNAMICS; FLUORINE ATOMS; METHYL GROUP; MOLECULAR SHUTTLE; ROTAXANES; SPEED BUMPS; STOP-AND-GO; UV LIGHT; VISIBLE LIGHT;

ACTIVATION ENERGY; BINDING SITES; FLUORINE; FREE ENERGY; HYDROCARBONS;

BINDING ENERGY;

ROTAXANE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENERGY; LIGHT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMODYNAMICS;

EID: 67949097288     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809225e     Document Type: Article

References (42)

1. Anelli, P.-L.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1991, 113, 5131-5133
2. (a) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605-7606.
3. (b) Cao, J. G.; Fyfe, M. C. T.; Stoddart, J. F.; Cousins, G. R. L.; Glink, P. T. J. Org. Chem. 2000, 65, 1937-1946.
4. (c) Kawaguchi, Y.; Harada, A. Ore. Lett. 2000, 2, 1353-1356.
5. (d) Leigh, D. A.; Troisi, A.; Zerbetto, F. Angew. Chem., Int. Ed. 2000, 39, 350-353.
6. (e) Collin, J. P.; Dietrich-Buchecker, C.; Gavina, P.; Jimenez-Molero, M. C.; Sauvage, J. P. Acc. Chem. Res. 2001, 34, 477-487.
7. (f) Kawai, H.; Umehara, T.; Fujiwara, K.; Tsuji, T.; Suzuki, T. Angew. Chem., Int. Ed. 2006, 45, 4281-4286.
8. (g) Yoon, I.; Miljanić, O. S.; Benitez, D.; Khan, S. I.; Stoddart, J. F. Chem. Commun. 2008, 4561-4563.
9. (a) Ashton, P. R.; Bissell, R. A.; Spencer, N.; Stoddart, J. F.; Tolley, M. S. Synlett 1992, 923-926.
10. (b) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133-137.
11. (c) Jeppesen, J. O.; Nielsen, K. A.; Perkins, J.; Vignon, S. A.; Di Fabio, A.; Ballardini, R.; Gandolfi, M. T.; Venturi, M.; Balzani, V.; Becher, J.; Stoddart, J. F. Chem.-Eur. J. 2003, 9, 2982-3007.
12. (d) Bottari, G.; Leigh, D. A.; Perez, E. M. J. Am. Chem. Soc. 2003, 125, 13360-13361.
13. (e) Aprahamian, I.; Dichtel, W. R.; Ikeda, T.; Heath, J. R.; Stoddart, J. F. Org. Lett. 2007, 9, 1287-1290.
14. Stoddart, J. F.; Colquhoun, H. M. Tetrahedron 2008, 64, 8231-8263.
15. Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H. R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414-417.
16. (a) Berna, J.; Leigh, D. A.; Lubomska, M.; Mendoza, S. M.; Perez, E. M.; Rudolf, P.; Teobaldi, G.; Zerbetto, F. Nat. Mater. 2005, 4, 704-710.
17. (b) Kay, E. R.; Leigh, D. A.; Zerbetto, F. Ansew. Chem., Int. Ed. 2007, 46, 72-191.
18. (c) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld; Wiley-VCH: Weinheim, Germany, 2008.
19. Bêlohradský, M.; Elizarov, A. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 2002, 67, 1719-1728.
20. Brough, B.; Northrop, B. H.; Schmidt, J. J.; Tseng, H.-R.; Houk, K. N.; Stoddart, J. F.; Ho, C.-M.Proc. Natl. Acad. Sci. U.S.A.2006, 103, 8583-8588.
21. (a) Asakawa, M.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Matthews, O. A.; Newton, S. P.; Raymo, F. M.; Shipway, A. N.; Spencer, N.; Quick, A.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem.-Eur. J. 1999, 5, 860-875.
22. (b) Around the same time, ABP units-both para-para and meta-meta disubstituted-were introduced into degenerate donor-acceptor [2]rotaxanes. Attempts to control shuttling by photoisomerization of the ABP units were, however, inconclusive; see: Kauffman, C.; Müller, W. M.; Vogtle, F.; Weinman, S.; Abramson, S.; Fuchs, B. Synthesis 1999, 84, 9-853.
23. (c) For a much more recent demonstration of the control of the shuttling rate in a degenerate, two-station, hydrogen-bonded [2]rotaxane by reversible photoisomerization of the ring size, see: Hirose, K.; Shiba, Y.; Ishibashi, K.; Doi, Y.; Tobe, Y. Chem.-Eur. J. 2008, 14, 3427-3433.
24. 4+ = Cyclobis(paraquat-p-phenylene); see: Asakawa, M.; Dehaen, W.; L'abbé, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Org. Chem. 1996, 61, 9591-9595.
25. 4+ has either low or no affinity towards the cisazobenzene moiety.
26. For a recent discussion of photoactivated moving parts in both molecules and integrated hybrid systems based on the photoisomerization of azobenzene derivatives, see: (a) Lu, J.; Choi, E.; Tamanoi, F.; Zink, J. I. Small 2008, 4, 421-428.
27. (b) A fine example of the use of a light-activated a-methyl stilbene "gate" in the functioning of a molecular information ratchet has been described recently; see: Serreli, V.; Lee, C. F.; Kay, E. R.; Leigh, D. A. Nature 2007, 445, 523-527.
28. Liu, Y.; Saha, S.; Vignon, S. A.; Flood, A. H.; Stoddart, J. F. Synthesis 2005, 3437-3445.
29. BHEEEEN = 1,5-bis[2-(2-(2-(2-hydroxy-ethoxy)ethoxy)ethoxy)ethoxy]- naphthalene; see: Ashton, P. R.; Huff, J.; Menzer, S.; Parsons, I. W.; Preece, J. A.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem.-Eur. J. 1996, 2, 31-44.
30. Sawada, T.; Yamada, M.; Thiemann, T.; Mataka, S. J. Chem. Soc., Perkin Trans. 1 2000, 16, 2623-2627.
31. Niemann, C.; Benson, A. A.; Mead, J. F. J. Am. Chem. Soc. 1941, 63, 2204-2208.
32. (a)Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628.
33. (b)Rostovtsev,V.V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Ansew. Chem., Int. Ed. 2002, 41, 2596-2599.
34. (c) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
35. (a) Dichtel, W. R.; Miljanić, O. Ŝ Spruell, J. M.; Heath, J. R.; Stoddart, J. F. J. Am. Chem. Soc. 2006, 128, 10388-10390.
36. (b) Miljanić, O. S.; Dichtel, W. R.; Aprahamian, I.; Rohde, R. D.; Agnew, H. D.; Heath, J. R.; Stoddart, J. F. OSAR 2 Comb. Sci. 2007, 26, 1165-1174.
37. max values of 355, 295, and 260 nm, respectively. Note that the fluorine substituents on the azobenzene ring system in 8 causes a 15 nm hypsochromic shift, and similar behavior was observed for the methyl substituted derivative 6.
38. -1; see: (a) Talaty, E. R.; Fargo, J. C. Chem. Commun. (London) 1967, 65-66.
39. (b) Lunak, S., Jr.; Nepras, M.; Hrdina, R.; Mustroph, H. Chem. Phys. 1994, 184, 255-260.
40. 6 experienced characteristic upfield shifts of-0.7,-1.4, and-5.3 ppm, respectively. For comparison see: Amabilino, D. B.; Anelli, P.-L.; Ashton, P. R.; Brown, G. R.; Córdova, E.; Godínez, L. A.; Hayes, W.; Kaifer, A. E.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11142-11170.
41. c see: Sutherland, I. O. Annu. Rep. NMR Spectrosc. 1971, 4, 71.
42. Kang, S. S.; Vignon, S. A.; Tseng, H.-R.; Stoddart, J. F. Chem.-Eur. J. 2004, 10, 2555-2564.