Facile catch and release of fullerenes using a photoresponsive molecular tube

Journal of the American Chemical Society

Volumn 135, Issue 35, 2013, Pages 12976-12979

  Kishi, Norifumi ^a   Akita, Munetaka ^a   Kamiya, Motoshi ^b   Hayashi, Shigehiko ^b   Hsu, Hsiu Fu ^c   Yoshizawa, Michito ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c TAMKANG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATCH AND RELEASE; EXTERNAL STIMULUS; FULLERENE C; PHOTO-RESPONSIVE; SINGLE MOLECULE;

TUBES (COMPONENTS);

FULLERENES;

ANTHRACENE; FULLERENE DERIVATIVE; LIGAND; NANOCAGE; NANOTUBE; PYRIDINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY; MASS SPECTROMETRY; MICROCAPSULE; MOLECULE; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 84883702687     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja406893y     Document Type: Article

References (43)

1. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry, 2 nd ed.; Wiley: Chichester, U.K., 2009.
2. Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
3. Pignataro, B. Molecules at Work; Wiley-VCH: Weinheim, Germany, 2012; Chapter 2.
4. Hiraoka, S.; Harano, K.; Shiro, M.; Shionoya, M. Angew. Chem., Int. Ed. 2005, 44, 2727
5. Durola, F.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2010, 49, 3189
6. Clever, G. H.; Shionoya, M. Chem.-Eur. J. 2010, 16, 11792
7. Shinkai, S.; Nakaji, T.; Ogawa, T.; Shigematsu, K.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 111
8. Irie, M.; Kato, M. J. Am. Chem. Soc. 1985, 107, 1024
9. Natali, M.; Giordani, S. Chem. Soc. Rev. 2012, 41, 4010
10. Ueno, A.; Yoshimura, H.; Saka, R.; Osa, T. J. Am. Chem. Soc. 1979, 101, 2779
11. Dube, H.; Ajami, D.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2010, 49, 3192
12. Clever, G. H.; Tashiro, S.; Shionoya, M. J. Am. Chem. Soc. 2010, 132, 9973
13. Zhang, L.; Macías, A.; Lu, T.; Gordon, J. I.; Gokel, G. W.; Kaifer, A. E. Chem. Commun. 1993, 1017
14. Bernardo, A. R.; Lu, T.; Córdova, E.; Zhang, L.; Gokel, G. W.; Kaifer, A. E. Chem. Commun. 1994, 529
15. Wang, Y.; Mendoza, S.; Kaifer, A. E. Inorg. Chem. 1998, 37, 317
16. Nijhuis, C. A.; Ravoo, B. J.; Huskens, J.; Reinhoudt, D. N. Coord. Chem. Rev. 2007, 251, 1761
17. Sun, W.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 2002, 124, 11570
18. Yoshizawa, M.; Kumazawa, K.; Fujita, M. J. Am. Chem. Soc. 2005, 127, 13456
19. Photoresponsive coordination cage with the ability of weak and strong guest bindings: Han, M.; Michel, R.; He, B.; Chen, Y.-S.; Stalke, D.; John, M.; Clever, G. H. Angew. Chem., Int. Ed. 2013, 52, 1319
20. Kadish, K. M.; Ruoff, R. S. Fullerenes: Chemistry, Physics, and Technology; Wiley: New York, 2000.
21. Cataldo, F.; Da Ros, T. Medicinal Chemistry and Pharmacological Potential of Fullerenes and Carbon Nanotubes; Springer: Dordrecht, The Netherlands, 2008.
22. Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250
23. Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189
24. Martìn, N.; Nierengarten, J.-F. Supramolecular Chemistry of Fullerenes and Carbon Nanotubes; Wiley-VCH: Weinheim, Germany, 2012.
25. Kawase, T.; Tanaka, K.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 1624
26. Kawase, T.; Tanaka, K.; Seirai, Y.; Shiono, N.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 5597
27. Kawase, T.; Fujikawa, N.; Tsutumi, M.; Oda, M.; Maeda, Y.; Wakahara, T.; Akasaka, T. Angew. Chem., Int. Ed. 2004, 43, 5060
28. Song, J.; Aratani, N.; Shinokubo, H.; Osuka, A. J. Am. Chem. Soc. 2010, 132, 16356
29. Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S. Angew. Chem., Int. Ed. 2011, 50, 8342
30. Xia, J.; Bacon, J. W.; Jasti, R. Chem. Sci. 2012, 3, 3018
31. Ikeda, A.; Yoshimura, M.; Udzu, H.; Fukuhara, C.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 4296
32. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 135
33. Fox, O. D.; Wilkinson, E. J. S.; Beer, P. D.; Drew, M. G. B. Chem. Commun. 2000, 391
34. Fox, O. D.; Cookson, J.; Wilkinson, E. J. S.; Drew, M. G. B.; MacLean, E. J.; Teat, S. J.; Beer, P. D. J. Am. Chem. Soc. 2006, 128, 6990
35. Suzuki, K.; Takao, K.; Sato, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 2544
36. Meng, W.; Breiner, B.; Rissanen, K.; Thoburn, J. D.; Clegg, J. K.; Nitschke, J. R. Angew. Chem., Int. Ed. 2011, 50, 3479
37. Canevet, D.; Pérez, E. M.; Martín, N. Angew. Chem., Int. Ed. 2011, 50, 9248
38. Li, M.-J.; Huang, C.-H.; Lai, C.-C.; Chiu, S.-H. Org. Lett. 2012, 14, 6146
39. Kishi, N.; Li, Z.; Yoza, K.; Akita, M.; Yoshizawa, M. J. Am. Chem. Soc. 2011, 133, 11438
40. Kishi, N.; Li, Z.; Sei, Y.; Akita, M.; Yoza, K.; Siegel, J. S.; Yoshizawa, M. Chem.-Eur. J. 2013, 19, 6313
41. Doigon, P.; Davis, T. W. J. Phys. Chem. 1952, 56, 764
42. Cunningham, J.; Heal, H. G. Trans. Faraday Soc. 1958, 54, 1355
43. 60 in MeCN is extremely low (< 0.0013 mM): Ruoff, R. S.; Tse, D. S.; Malhotra, R.; Lorents, D. C. J. Phys. Chem. 1993, 97, 3379-3383