Syntheses and magnetic properties of stable organic triradicals with quartet ground states consisting of different nitroxide radicals

Journal of the American Chemical Society

Volumn 120, Issue 29, 1998, Pages 7168-7173

  Tanaka, Megumi ^a   Matsuda, Kenji ^a   Itoh, Tetsuji ^a   Iwamura, Hiizu ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b National Institution for Academic Degrees and University Evaluation Tokyo   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIS[(1 OXY 3 OXIDE 4,4,5,5 TETRAMETHYLIMIDAZOLIN 2 YL)PHENYL]NITROXIDE; NITROXIDE; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; CHEMICAL STRUCTURE; CRYSTAL; CYCLIC POTENTIOMETRY; ELECTRON SPIN RESONANCE; MAGNETISM; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032578201     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980817g     Document Type: Article

References (39)

1. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
2. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
3. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
4. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
5. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
6. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
7. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
8. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
9. For reviews see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346. (d) Miller, J. S.; Epstein A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. (e) Rajca, A. Chem. Rev. 1994, 94, 871. (f) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, Oct 2, 30. (g) Kahn, O. Molecular Magnetism; VCH: New York, 1993. (h) Kahn, O. Adv. Inorg. Chem. 1995, 43, 179. (i) Murray, K. S. Adv. Inorg. Chem. 1995, 43, 261.
10. (a) Itoh, K. Chem. Phys. Lett. 1967, 1, 235.
11. (b) Mataga, N. Theor. Chim. Acta 1968, 10, 372.
12. (c) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550.
13. (d) Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483.
14. Ishida, T.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 4238.
15. (a) Caneschi, A.; Gatteschi, D.; Grand, A.; Laugier, J.; Pardi, L.; Rey, P. Inorg. Chem. 1988, 27, 1031.
16. (b) Caneschi, A.; Gatteschi, D.; Renard, J. P.; Rey, P. Sessoli, R. J. Am. Chem. Soc. 1989, 111, 785.
17. (c) Cabello, C. I.; Caneschi, A.; Carlin, R. L.; Gatteschi, D.; Rey, P. Sessoli, R. Inorg. Chem. 1990, 29, 2582.
18. (d) Caneschi, A.; Fabrizio, F.; Gatteschi, D.; Rey, P.; Sessoli, R. Inorg. Chem. 1991, 30, 3162.
19. (e) Inoue, K.; Iwamura, H. J. Am. Chem. Soc. 1994, 116, 3173.
20. (f) Inoue, K. Iwamura, H. J. Chem. Soc., Chem. Commn. 1994, 2274.
21. (g) Inoue, K.; Hayamizu T.; Iwamura, H. Chem. Lett. 1995, 745.
22. (h) Inoue, K.; Iwamura, H. Synth. Met. 1995, 71, 1793.
23. (i) Inoue, K.; Hayamizu, T.; Iwamura, H. Mol. Cryst. Liq. Cryst. 1995, 273, 67.
24. (j) Inoue, K.; Iwamura, H. Adv. Mater. 1996, 8, 73.
25. (k) Inoue, K.; Hayamizu, T.; Iwamura, H.; Hashizume D.; Ohashi, Y. J. Am. Chem. Soc. 1996, 118, 1803.
26. (l) Iwamura, H.; Inoue K.; Hayamizu, T. Pure Appl. Chem. 1996, 68, 243.
27. (m) Inoue K.; Iwamura, H. Mol. Cryst. Liq. Cryst. 1996, 286, 133.
28. (n) Markosyan, A. S. Hayamizu, T.; Iwamura H.; Inoue, K. J. Phys., Condens. Matter 1998, 10, 2323.
29. (a) Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Phys. Chem. 1993, 97, 13267.
30. (b) Fujita, J.; Tanaka, M.; Suemune, H.; Koga, N.; Matsuda, K.; Iwamura H. J. Am. Chem. Soc. 1996, 118, 9347.
31. (c) Fujita, J.; Matsuoka, Y.; Matsuo, K.; Tanaka, M.; Akita T.; Koga, N.; Iwamura H. J. Chem. Soc., Chem. Commun. 1997, 2393. There are several examples of high-spin molecules (S ≥ 3/2), but not all species satisfy the requirement of stability and ligating ability. See: Nau, W. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2445.
32. (c) Fujita, J.; Matsuoka, Y.; Matsuo, K.; Tanaka, M.; Akita T.; Koga, N.; Iwamura H. J. Chem. Soc., Chem. Commun. 1997, 2393. There are several examples of high-spin molecules (S ≥ 3/2), but not all species satisfy the requirement of stability and ligating ability. See: Nau, W. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2445.
33. (a) Inoue, K.; Iwamura, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 917.
34. (b) Hosokoshi, Y.; Takizawa, K.; Nakano, H.; Goto, T.; Takahashi, M.; Inoue, K. J. Magn. Magn. Mater. 1998, 177-181, 634. We thank Prof. Katsuya Inoue for information prior to publication.
35. Lamchen, M. Mittag, T. W. J. Chem. Soc. C 1966, 2300.
36. Ullman, E. F.; Call, L.; Osiecki, J. H. J. Org. Chem. 1970, 35, 3623.
37. Ullman, E. F.; Osiecki, J. H.; Boocock, D. G. B.; Darcy, R. J. Am. Chem. Soc. 1972, 94, 7049.
38. Nakazono, S.; Karasawa, S.; Koga, N.; Iwamura, H. Angew. Chem., Int. Ed. Engl. in press.
39. Tyutyulkov, N. N.; Karabunarliev, S. C. Int. J. Quantum Chem. 1986, 29, 1325.