Hemicarceplex formation with a cyclotriveratrylene-based molecular cage allows isolation of high-purity (≥99.0%) C70 directly from fullerene extracts

Organic Letters

Volumn 14, Issue 24, 2012, Pages 6146-6149

  Li, Ming Jhe ^a   Huang, Chi Hao ^a   Lai, Chien Chen ^b   Chiu, Sheng Hsien ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOTRIVERATRYLENE; FULLERENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

FULLERENES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS;

EID: 84871569115     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3027957     Document Type: Article

References (43)

1. Hirsch, A.; Brettreich, M. Fullerenes: Chemistry and Reactions; Wiley-VCH: Weinheim, 2005.
2. Langa, F., Nierengarten, J.-F., Eds. Fullerenes: Principles and Applications; Royal Society of Chemistry: Cambridge, 2007.
3. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162-163
4. Scrivens, W. A.; Bedworth, P. V.; Tour, J. M. J. Am. Chem. Soc. 1992, 114, 7917-7919
5. Khemani, K. C.; Prato, M.; Wudl, F. A. J. Org. Chem. 1992, 57, 3254-3256
6. Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229-231
7. Brabec, C. J.; Dyakonov, V.; Scherf, U., Eds. Organic Photovoltaics: Materials, Device Physics, and Manufacturing Technologies; Wiley-VCH: Weinheim, 2008.
8. Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerstrom, O. J. Chem. Soc., Chem. Commun. 1992, 604-606
9. Atwood, J. L.; Barbour, L. J.; Raston, C. L.; Sudria, I. B. N. Angew. Chem., Int. Ed. 1998, 37, 981-983
10. Felder, D.; Heinrich, B.; Guillon, D.; Nicoud, J.-F.; Nierengarten, J.-F. Chem.-Eur. J. 2000, 6, 3501-3507
11. Kubo, Y.; Sugasaki, A.; Ikeda, M.; Sugiyasu, K.; Sonoda, K.; Ikeda, A.; Takeuchi, M.; Shinkai, S. Org. Lett. 2002, 4, 925-928
12. Kawase, T.; Tanaka, K.; Fujiwara, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 1624-1628
13. Sato, H.; Tashiro, K.; Shinmori, H.; Osuka, A.; Murata, Y.; Komatsu, K.; Aida, T. J. Am. Chem. Soc. 2005, 127, 13086-13087
14. Hosseini, A.; Taylor, S.; Accorsi, G.; Armaroli, N.; Reed, C. A.; Boyd, P. D. W. J. Am. Chem. Soc. 2006, 128, 15903-15913
15. Huerta, E.; Isla, H.; Perez, E. M.; Bo, C.; Martin, N.; de Mendoza, J. J. Am. Chem. Soc. 2010, 132, 5351-5353
16. Gil-Ramirez, G.; Karlen, S. D.; Shundo, A.; Porfyrakis, K.; Ito, Y.; Briggs, G. A. D.; Morton, J. J. L.; Anderson, H. L. Org. Lett. 2010, 12, 3544-3547
17. Canevet, D.; Perez, E. M.; Martin, N. Angew. Chem., Int. Ed. 2011, 50, 9248-9259
18. Martin, N.; Nierengarten, J.-F. Supramolecular Chemistry of Fullerenes and Carbon Nanotubes; Wiley-VCH: Weinheim, 2012.
19. Matsubara, H.; Oguri, S.; Asano, K.; Yamamoto, K. Chem. Lett. 1999, 431-432
20. Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; de Mendoza, J. Angew. Chem., Int. Ed. 2007, 46, 202-205
21. Zhang, C.; Wang, Q.; Long, H.; Zhang, W. J. Am. Chem. Soc. 2011, 133, 20995-21001
22. Kishi, N.; Li, Z.; Yoza, K.; Akita, M.; Yoshizawa, M. J. Am. Chem. Soc. 2011, 133, 11438-11441
23. Jurow, M.; Farley, C.; Pabon, C.; Hageman, B.; Dolor, A.; Drain, C. M. Chem. Commun. 2012, 48, 4731-4733
24. Ro, S.; Rowan, S. J.; Pease, A. R.; Cram, D. J.; Stoddart, J. F. Org. Lett. 2000, 2, 2411-2414
25. Warmuth, R. Acc. Chem. Res. 2001, 34, 95-105
26. Sherman, J. C. Chem. Commun. 2003, 14, 1617-1623
27. Warmuth, R.; Makowiec, S. J. Am. Chem. Soc. 2005, 127, 1084-1085
28. Liu, Y.; Warmuth, R. Org. Lett. 2007, 9, 2883-2886
29. Hardie, M. J. Chem. Soc. Rev. 2010, 39, 516-527
30. Matsubara, H.; Hasegawa, A.; Shiwaku, K.; Asano, K.; Uno, M.; Takahashi, S.; Yamamoto, K. Chem. Lett. 1998, 923-924
31. Matsubara, H.; Shimura, T.; Hasegawa, A.; Semba, M.; Asano, K.; Yamamoto, K. Chem. Lett. 1998, 1099-1100
32. Huerta, E.; Cequier, E.; de Mendoza, J. Chem. Commun. 2007, 5016-5018
33. Brotin, T.; Roy, V.; Dutasta, J.-P. J. Org. Chem. 2005, 70, 6187-6195
34. Quan, M. L. C.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754-2755
35. Houk, K. N.; Nakamura, K.; Sheu, C.; Keating, A. E. Science 1996, 273, 627-629
36. Diederich, F.; Whetten, R. L. Acc. Chem. Res. 1992, 25, 119-126
37. Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2004, 126, 6570-6571
38. Lu, X.; Akasaka, T.; Nagase, S. Angew. Chem., Int. Ed. 2012, 51, 2812-2814
39. Hummelen, J. C.; Bellavia-Lund, C.; Wudl, F. Top. Curr. Chem. 1999, 199, 93-143
40. Vostrowsky, O.; Hirsch, A. Chem. Rev. 2006, 106, 5191-5207
41. Rodriguez-Fortea, A.; Balch, A. L.; Poblet, J. M. Chem. Soc. Rev. 2011, 40, 3551-3563
42. Liu, G.; Wu, Y.; Porfyrakis, K. Curr. Org. Chem. 2011, 15, 1197-1207
43. Von dem Bussche-Hunnefeld, C.; Buhring, D.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1995, 1085-1087