Hexaazaphenalene derivatives: One-pot synthesis, hydrogen-bonded chiral helix, and fluorescence properties

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5036-5039

  Suzuki, Shuichi ^a,b   Fukui, Kozo ^b   Fuyuhiro, Akira ^a   Sato, Kazunobu ^b   Takui, Takeji ^b   Nakasuji, Kazuhiro ^a   Morita, Yasushi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78049499412     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102200v     Document Type: Article

References (39)

1. Reid, D. H. Chem. Ind. (London) 1956, 1504-1505
2. Pettit, R. Chem. Ind. (London) 1956, 1306-1307
3. Pettit, R. J. Am. Chem. Soc. 1960, 82, 1972-1975
4. Reid, D. H. Quart. Rev. 1965, 19, 274-302
5. Suzuki, S.; Morita, Y.; Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Nakasuji, K. J. Am. Chem. Soc. 2006, 128, 2530-2531
6. Nishida, S.; Morita, Y.; Ueda, A.; Kobayashi, T.; Fukui, K.; Ogasawara, K.; Sato, K.; Takui, T.; Nakasuji, K. J. Am. Chem. Soc. 2008, 130, 14954-14955
7. Recent overview of the phealenyl chemistry
8. Morita, Y.; Nishida, S. Phenalenyls, Cyclopentadienyls, and Other Carbon-Centered Radicals. In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R., Ed.; John Wiley & Sons Ltd.: West Sussex, 2010; Chapter 3, pp 81 - 145.
9. Pal, S. K.; Itkis, M. E.; Tham, F. S.; Reed, R. W.; Oakley, R. T.; Haddon, R. C. Science 2005, 309, 281-284
10. Kubo, T.; Goto, Y.; Uruichi, M.; Yakushi, K.; Nakano, M.; Fuyuhiro, A.; Morita, Y.; Nakasuji, K. Chem. Asian J. 2007, 2, 1370-1379
11. Kubo, T.; Shimizu, A.; Sakamoto, M.; Uruichi, M.; Yakushi, K.; Nakano, M.; Shiomi, D.; Sato, K.; Takui, T.; Morita, Y.; Nakasuji, K. Angew. Chem., Int. Ed. 2005, 44, 6564-6568
12. Chikamatsu, M.; Mikami, T.; Chisaka, J.; Yoshida, Y.; Azumi, R.; Yase, K.; Shimizu, A.; Kubo, T.; Morita, Y.; Nakasuji, K. Appl. Phys. Lett. 2007, 91 043506
13. Morita, Y.; Nishida, S.; Kawai, J.; Fukui, K.; Nakazawa, S.; Sato, K.; Shiomi, D.; Takui, T.; Nakasuji, K. Org. Lett. 2002, 4, 1985-1988
14. Morita, Y.; Nishida, S.; Kawai, J.; Takui, T.; Nakasuji, K. Pure Appl. Chem. 2008, 80, 507-517
15. Morita, Y.; Okafuji, T.; Sato, M. Jpn. Kokai Tokkyo Koho JP 2007-227186 A 20070906, 2007.
16. Morita, Y.; Aoki, T.; Fukui, K.; Nakazawa, S.; Tamaki, K.; Suzuki, S.; Fuyuhiro, A.; Yamamoto, K.; Sato, K.; Shiomi, D.; Naito, A.; Takui, T.; Nakasuji, K. Angew. Chem., Int. Ed. 2002, 41, 1793-1796
17. Morita, Y.; Suzuki, S.; Fukui, K.; Nakazawa, S.; Kitagawa, H.; Kishida, H.; Okamoto, H.; Naito, A.; Sekine, A.; Ohashi, Y.; Shiro, M.; Sasaki, K.; Shiomi, D.; Sato, K.; Takui, T.; Nakasuji, K. Nat. Mater. 2008, 7, 48-51
18. Zheng, S.; Lan, J.; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 2003, 125, 5786-5791
19. Zheng, S.; Thompson, J. D.; Tontcheva, A.; Khan, S. I.; Rubin, Y. Org. Lett. 2005, 7, 1861-1863
20. Suzuki, S.; Morita, Y.; Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Nakasuji, K. Inorg. Chem. 2005, 44, 8197-8198
21. Murata, T.; Morita, Y.; Fukui, K.; Tamaki, T.; Yamochi, H.; Sato, G.; Nakasuji, K. Bull. Chem. Soc. Jpn. 2006, 79, 894-913
22. Tian, Y.-H.; Kertesz, M. J. Am. Chem. Soc. 2010, 132, 10648-10649
23. Mota, F.; Miller, J. S.; Novoa, J. J. J. Am. Chem. Soc. 2009, 131, 7699-7707
24. Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850-13858
25. Tian, Y.-H.; Huang, J.; Kertesz, M. Phys. Chem. Chem. Phys. 2010, 12, 5084-5093
26. Tomlin, C. D. S. Diss. Abstr. 1965, 26, 105; Chem. Abstr. 1965, 63, 16354g.
27. Trofimenko, S.; Little, E. L., Jr.; Mower, H. F. J. Org. Chem. 1962, 27, 433-438
28. Graboyes, H.; Jaffe, G. E.; Pachter, I. J.; Rosenbloom, J. P.; Villani, A. J.; Wilson, J. W.; Weinstock, J. J. Med. Chem. 1968, 11, 568-573
29. 6: C, 67.03; H, 8.29; N, 24.68. Found: C, 66.83; H, 8.17; N, 24.57.
30. -and its crystal structure have been recently reported. See: Jiang, Y.; Zhang, H.; Wan, X.; Xue, X.; Liu, Y.; Song, H.; Yu, A.; Chen, Y. Z. Naturforsch., B: Chem. Sci. 2008, 63, 1425-1430
31. w = 0.1090, GOF = 1.067.
32. w = 0. 2081, GOF = 1.126.
33. Unfortunately, the absolute configuration could not be identified because the refinement of flack parameter was not possible in the X-ray crystal structure analysis.
34. - for the CD measurement, the Cotton effect was not observed, which indicates that formation of an almost 1:1 mixture of the right- and left-handed H-bonded helices and chirality enrichment did not occur under the crystallization process.
35. Recent reviews
36. Matsuura, T.; Kojima, H. J. Photochem. Photobiol. C 2005, 6, 7-24
37. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry, 2 nd ed.; John Wiley & Sons Ltd.: West Sussex, 2009; pp 687 - 691.
38. 0.9: C, 61.36; H, 9.01; N, 17.95. Found: C, 61.28; H, 8.99; N, 17.99.
39. w = 0.2245, GOF = 1.068.