Spin-carrying benzoquinone derivatives

Journal of Organic Chemistry

Volumn 74, Issue 24, 2009, Pages 9345-9350

  Nakatsuji, Shin'ichi ^a   Nobusawa, Mitsunori ^a   Suzuki, Hideto ^a   Akutsu, Hiroki ^a   Yamada, Jun Ichi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONES; BLACK CRYSTALS; CHEMICAL EQUATIONS; NEIGHBORING MOLECULES; NITROXIDES; RECRYSTALLIZATIONS; TEMPO RADICAL;

CHEMICAL REACTIONS;

OXYGEN;

BENZOQUINONE DERIVATIVE; FLUORANIL; NITROXIDE; OXYGEN;

ABSORPTION; ARTICLE; COMPLEX FORMATION; CRYSTAL; CRYSTAL STRUCTURE; CRYSTALLIZATION; DONOR; MAGNETISM; MOLECULE; OXIDATION REDUCTION REACTION; ULTRAVIOLET RADIATION;

EID: 73149107473     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902007m     Document Type: Article

References (41)

1. Cf: (a) Bent, H. A. Chem. Rev. 1968, 68, 587.
2. (b) Organic Charge-transfer Complexes; Foster, R., Ed.; Academic Press: London, UK, 1969.
3. (c) The Donor-Acceptor Approach to Molecular Interactions; Gutmann, V., Ed.; Plenum Press: New York, 1978.
4. Cf.: (a) Organic Chemistry in Colour; Gordon, P. F., Gregory, P., Eds.; Springer-Verlag: Berlin, Germany, 1987.
5. (b) Color Chemistry; Zollinger, H., Ed.; Verlag Helvetica Chimica Acta: Zürich, Switzerland, 2003.
6. (c) Shirinian, V. Z., Shimkin, A. A. In Heterocyclic Polymethine Dyes: Synthesis, Properties and Applications; Topics in Heterocyclic Chemistry, Vol. 14, Springer-Verlag: Berlin, Germany, 2008; Chapter 5.
7. Cf.: (a) Metzger, R. M. Acc. Chem. Res. 1999, 32, 950.
8. (b) Metzger, R. M. Chem. Rev. 2003, 103, 3803.
9. (a) Becker, J. Y.; Bernstein, J.; Bittner, S.; Levi, N.; Shaik, S. S. J. Am. Chem. Soc. 1983, 105, 4468.
10. (b) Becker, J. Y.; Bernstein, J.; Bittner, S.; Levi, N.; Shaik, S. S.; Zer-Zion, N. J. Org. Chem. 1988, 53, 1689.
11. (c) Marin, N.; Segura, J. L.; Seoane, C.; Orti, E.; Viruala, R.; Albert, A.; Cano, F. H.; Vidal-Gancedo, J.; Rovira, C.; Veciana, J. J. Org. Chem. 1996, 61, 3041.
12. (d) Narvor, N. L; Robertson, N.; Weyland, T.; Kilburn, J. D.; Underhill, A. E.; Webster, M.; Svenstrup, N.; Becher, J. Chem. Commun. 1996, 1363.
13. (e) Ueda, K.; Goto, M.; Iwamatsu, M.; Sugimoto, T.; Endo, S.; Toyota, N.; Yamamoto, K.; Fujita, H. J. Mater. Chem. 1998, 8, 2195.
14. (f) Kobayashi, A.; Tanaka, H.; Kumasaki, M.; Torii, H.; Narymbetov, B.; Adachi, T. J. Am. Chem. Soc. 1999, 121, 10763.
15. (g) Iwamatsu, M.; Kominami, T.; Ueda, K.; Sugimoto, T.; Adachi, T.; Fujita, H.; Yoshino, H.; Mizuno, Y.; Murata, K.; Shiro, M. Inorg. Chem. 2000, 39, 3810.
16. (h) Tanaka, H.; Okano, Y.; Kobayashi, H.; Suzuki, W.; Kobayashi, A. Science 2001, 291, 285.
17. (i) Belo, D.; Alves, H.; Lopes, E. B.; Duarte, M. T.; Gama, V.; Henriques, R. T.; Almeida, M.; Pérez-Benítez, A.; Rovira, C.; Veciana, J. Chem.;Eur. J. 2001, 7, 511.
18. (a) Cordes, A. W.; Haddon, R. C.; Oakley, R. T.; Schneemeyer, L. F.; Waszczak, J. V.; Young, K. M.; Zimmerman, N. M. J. Am. Chem. Soc. 1991, 113, 582.
19. (b) Tsubata, Y.; Suzuki, T.; Miyashi, T.; Yamashita, Y. J. Org. Chem. 1992, 57, 6749.
20. (a) Sugano, T.; Fukasawa, T.; Kinoshita, M. Synth. Met. 1991, 43, 3281.
21. (b) Sugimoto, T.; Yamaga, S.; Nakai, M.; Tsuji, M.; Nakatsuji, H.; Hoshino, N. Chem. Lett. 1993, 1817.
22. (c) Ishida, T.; Tomioka, K.; Nogami, T.; Yamaguchi, K.; Mori, W.; Shirota, Y. Mol. Cryst. Liq. Cryst. 1993, 232, 99.
23. (d) Kumai, R.; Matsushita, M. M.; Izuoka, A.; Sugawara, T. J. Am. Chem. Soc. 1994, 116, 4523.
24. (e) Nakatsuji, S.; Anzai, H. J. Mater. Chem. 1997, 7, 2161.
25. (f) Fujiwara, H.; Lee, H.-J.; Kobayashi, H.; Fujiwara, E.; Kobayashi, A. Chem. Lett. 2003, 482.
26. (g) Mukai, K.; Senda, N.; Hatanaka, T.; Minakuchi, H.; Ohara, K.; Taniguchi, T.; Misaki, Y.; Hosokoshi, Y.; Inoue, K.; Azuma, N. Inorg. Chem. 2004, 43, 566.
27. (h) Matsushita, M. M.; Kawakami, H.; Sugawara, T.; Ogata, M. Phys. Rev. 2008, B77, 195208.
28. (i) Masuda, Y.; Kuratsu, M.; Suzuki, S.; Kozaki, M.; Shiomi, D.; Sato, K.; Takui, T.; Hosokoshi, Y.; Lan, X.-Z.; Miyazaki, Y.; Inaba, A.; Okada, K. J. Am. Chem. Soc. 2009, 131, 4670.
29. (a) Nakatsuji, S. Adv. Mater. 2001, 13, 1719.
30. (b) Nakatsuji, S. In Nitroxides: Applications in Chemistry, Biomedicine, and Materials Science; Likhtenstein, G. I., Yamauchi, J., Nakatsuji, S., Smirnov, A. I., Tamura, R., Eds.; Wiley-VCH: Weinheim, Germany, 2008; Chaptor 5, p 161.
31. Nakatsuji, S.; Akashi, N.; Suzuki, K.; Enoki, T.; Anzai, H. J. Chem. Soc., Perkin Trans. 2 1996, 2555.
32. Nakatsuji, S.; Takai, A.; Nishikawa, K.; Morimoto, Y.; Yasuoka, N.; Suzuki, K.; Enoki, T.; Anzai, H. J. Mater. Chem. 1999, 9, 1747.
33. A portion of this work has appeared in a preliminary communication: Nobusawa, M.; Akutsu, H.; Yamada, J.; Nakatsuji, S. Chem. Lett. 2008, 37, 788.
34. (a) Neef, R.; Bayer, O. Chem. Ber. 1957, 90, 1137.
35. (b) Nogami, T.; Yamaoka, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 380.
36. (c) Shaaban, I.; Solima, R. Pharmazie 1978, 33, 642.
37. (d) Iwatsuki, S.; Kubo, M.; Iwase, H. Chem. Lett. 1993, 517.
38. The preparations and some properties of the corresponding chloroand bromo-derivative of 7 are reported in ref 8, although neither crystal structure determinations nor susceptibility measurements were carried out on the compounds.
39. Neither single-crystal X-ray analysis of 4c nor its powder X-ray diffraction measurement to see if its crystal structure is isomorphic with that of 4a or 4b was successful probably due to its glassy nature.
40. (a) Minguet, M.; Amabilino, D. B.; Vidal-Gancedo, J.; Wurst, K.; Veciana, J. J. Mater. Chem. 2002, 12, 570.
41. B-value of -154 K is the largest one reported so far among the nitroxide-based radical compounds.