Molecular actuator: Redox-controlled clam-like motion in a bichromophoric electron donor

Organic Letters

Volumn 11, Issue 9, 2009, Pages 1939-1942

  Chebny, Vincent J ^a   Shukla, Ruchi ^a   Lindeman, Sergey V ^a   Rathore, Rajendra ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66149114088     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900371m     Document Type: Article

References (33)

1. (a) Introduction to Molecular Electronics, Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Oxford Univ. Press: New York, 1995.
2. (b) Maiya, B. G.; Ramasarma, T. Curr. Sci. 2001, 80, 1523.
3. (a) Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. AcchChemk Res. 2001, 34, 159-170.
4. (b) Grimme, W.; Kaemmerling, H. T.; Lex, J.; Gleiter, R.; Heinze, J.; Dietrich, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 205, and references cited therein.
5. (a) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
6. (b) Chebny, V. J.; Rathore, R. J. Am. Chem. Soc. 2007, 129, 8458, and references therein.
7. (a) Marsella, M. J.; Reid, R. J. Macromolecules 1999, 32, 5982.
8. (b) Tseng, H.-R.; Vignon, S. A.; Stoddart, J. F. Polym. Prepr. 2003, 44, 377.
9. (a) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
10. (b) Feringa, B. L. J. Org. Chem. 2007, 72, 6635.
11. (c) Rathore, R.; Magueres, P. L.; Lindeman, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. 2000, 39, 809.
12. (d) McQuade, T. D.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537, and references cited therein.
13. (a) Kaifer, A. E.; Stoddart, J. F. Nature (London) 1994, 369, 133.
14. (b) Grossel, M. C. Nanomater. Chem. 2007, 319.
15. (c) Saha, S.; Stoddart, J. F. Funct. Org. Mat. 2007, 295.
16. (a) Baughman, R. H. Synth. Met. 1996, 78, 339.
17. (b) Song, C.; Swager, T. M. Org. Lett. 2008, 10, 3575, and references cited therein.
18. Mataka, S.; Shigaki, K.; Sawada, T.; Mitoma, Y.; Taniguchi, M.; Thiemann, T.; Ohga, K.; Egashira, N. Angew. Chem., Int. Ed. 1998, 37, 2352.
19. Also see: Mataka, S.; Takahashi, K.; Hirota, T.; Takuma, K.; Kobayashi, H.; Tashiro, M.; Imada, K.; Kuniyoshi, M. J. Org. Chem. 1986, 51, 4618.
20. Lavoisier-Gallo, T.; Rodriguez, J. Synth. Commun. 1998, 28, 2259.
21. Bovey, F. A. Nuclear Magnetic Resonance Spectroscopy; Academic Press: New York, 1969; Chapter VII.
22. Rathore, R.; Abdelwahed, S. H.; Guzei, I. A. J. Am. Chem. Soc. 2003, 125, 8712, and references cited therein.
23. (a) Singer, L. A.; Cram, D. J. J. Am. Chem. Soc. 1963, 85, 1080.
24. (b) Taniguchi, M.; Mataka, S.; Thiemann, T.; Sawada, T.; Mimura, K.; Mitoma, Y. Bull. Chem. Soc. Jpn. 1998, 71, 2661.
25. (c) Rathore, R.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 9343, and references therein.
26. Compare: Rathore, R.; Chebny, V. J.; Kopatz, E. J.; Guzei, I. A. Angew. Chem., Int. Ed. 2005, 44, 2771.
27. (a) Nelsen, S. F. Chem.-Eur. J. 2000, 6, 581.
28. (b) Badger, B.; Brocklehurst, B. Nature (London) 1968, 219, 263.
29. (c) Kochi, J. K.; Rathore, R.; Le Magueres, P. J. Org. Chem. 2000, 65, 6826.
30. Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Synth. 2005, 82, 1.
31. Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887.
32. + induces a slight distortion in the chairlike conformations of the 7-membered rings in bicyclododecane framework from the ideal chair conformations.
33. Compare: Banerjee, M.; Vyas, V. S.; Lindeman, S. V.; Rathore, R. Chem. Commun. 2008, 1889.