Air- and heat-stable planar tri-p-quinodimethane with distinct biradical characteristics

Journal of the American Chemical Society

Volumn 133, Issue 41, 2011, Pages 16342-16345

  Zhu, Xiaozhang ^a   Tsuji, Hayato ^a   Nakabayashi, Koji ^a   Ohkoshi, Shin Ichi ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; AMBIENT LIGHT; NEAR-IR LIGHT; ROOM TEMPERATURE; SYNTHETIC APPROACH; THERMALLY STABLE; TWO-ELECTRON OXIDATION;

ENERGY GAP;

METHANE; NITROGEN; OLIGO 4 QUINODIMETHANE; TRI 4 QUINODIMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONJUGATION; CYCLIC POTENTIOMETRY; ELECTRON; ENERGY; LIGHT ABSORPTION; OXIDATION REDUCTION POTENTIAL; ROOM TEMPERATURE; SYNTHESIS; THERMOSTABILITY;

AIR; FLEROXACIN; FREE RADICALS; HOT TEMPERATURE; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 80054749092     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206060n     Document Type: Article

References (30)

1. Dowd, P. Acc. Chem. Res. 1972, 5, 242
2. Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1
3. Szwarc, M. Discuss. Faraday Soc. 1947, 2, 46
4. Thiele, J.; Balhorn, H. Chem. Ber. 1904, 37, 1463
5. Chichibabin, A. E. Chem. Ber. 1907, 40, 1810
6. Takahashi, T.; Matsuoka, K.-I.; Takimiya, K.; Otsubo, T.; Aso, Y. J. Am. Chem. Soc. 2005, 127, 8928
7. Ortiz, R. P.; Casado, J.; Hernández, V.; Navarrete, J. T. L.; Viruela, P. M.; Ortí, E.; Takimiya, K.; Otsubo, T. Angew. Chem., Int. Ed. 2007, 46, 9057
8. Kikuchi, A.; Iwahori, F.; Abe, J. J. Am. Chem. Soc. 2004, 126, 6526
9. Porter, W. W., III; Vaid, T. P.; Rheingold, A. L. J. Am. Chem. Soc. 2005, 127, 16559
10. Ueda, A.; Nishida, S.; Fukui, K.; Ise, T.; Shiomi, D.; Sato, K.; Takui, T.; Nakasuji, K.; Morita, Y. Angew. Chem., Int. Ed. 2010, 49, 1678
11. Koide, T. K.; Furukawa, K.; Shinokubo, H.; Shin, J.-Y.; Kim, K. S.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2010, 132, 7246
12. Kubo, T.; Sakamoto, M.; Akabane, M.; Fujiwara, Y.; Yamamoto, K.; Akita, M.; Inoue, K.; Takui, T.; Nakasuji, K. Angew. Chem., Int. Ed. 2004, 43, 6474
13. Konishi, A.; Hiro, Y.; Nakano, M.; Shimizu, A.; Botek, E.; Champagne, B.; Shiomi, D.; Sato, K.; Takui, T.; Matsumoto, K.; Kurata, H.; Kubo, T. J. Am. Chem. Soc. 2010, 132, 11021
14. Shimizu, A.; Kubo, T.; Uruichi, M.; Yakushi, K.; Nakano, M.; Shiomi, D.; Sato, K.; Takui, T.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Morita, Y.; Nakasuji, K. J. Am. Chem. Soc. 2010, 132, 14421
15. Lambert, C. Angew. Chem., Int. Ed. 2011, 50, 1756
16. Casado, J.; Zgierski, M. Z.; Ewbank, P. C.; Burand, M. W.; Janzen, D. E.; Mann, K. R.; Pappenfus, T. M.; Berlin, A.; Pérez-Inestrosa, E.; Ortiz, R. P.; Navarrete, J. T. L. J. Am. Chem. Soc. 2006, 128, 10134
17. Jonkman, H. T.; Kommandeur, J. Chem. Phys. Lett. 1972, 15, 496
18. Zhu, X.; Mitsui, C.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 13596
19. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem. 1988, 53, 2093
20. Licha, K.; Riefke, B.; Ntziachristos, V.; Becker, A.; Chance, B.; Semmler, W. Photochem. Photobiol. 2000, 72, 392
21. Pappenfus, T. M.; Raff, J.; Hukkanen, E. J.; Burney, J. R.; Casado, J.; Drew, S. M.; Miller, L. L.; Mann, K. R. J. Org. Chem. 2002, 67, 6015
22. Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E. Heteroatom. Chem. 2011, 22, 316
23. Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 11902
24. Tsuji, H.; Yokoi, Y.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. Chem.-Asian J. 2009, 4, 655
25. Ilies, L.; Tsuji, H.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 4240
26. Kamada, K.; Ohta, K.; Kubo, T.; Shimizu, A.; Morita, Y.; Nakasuji, K. Angew. Chem., Int. Ed. 2007, 46, 3544
27. Chikamatsu, M.; Mikami, T.; Chisaka, J.; Yoshida, Y.; Aumi, R.; Yase, K.; Shimizu, A.; Kubo, T.; Morita, Y.; Nakasuji, K. Appl. Phys. Lett. 2007, 91, 043506
28. Suzuki, Y.; Miyazaki, E.; Takimiya, K. J. Am. Chem. Soc. 2010, 132, 10453
29. Matsuo, Y.; Sato, Y.; Niinomi, T.; Soga, I.; Tanaka, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 16048
30. Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E. Adv. Mater. 2009, 21, 3776