Triradical cation of p-phenylenediamine having two nitroxide radical groups: Spin alignment mediated by delocalized spin

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2948-2953

  Ito, Akihiro ^a   Nakano, Yoshiaki ^a   Urabe, Masashi ^a   Kato, Tatsuhisa ^b   Tanaka, Kazuyoshi ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b JOSAI UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; NITROGEN OXIDES; POSITIVE IONS;

CATIONIC STATE; DELOCALIZED SPIN; SPIN ALIGNMENT;

AMINES;

CATION; NITROXIDE; PHENYLENEDIAMINE; RADICAL;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; SPECTROMETER; STRUCTURE ANALYSIS;

EID: 33644946504     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056318e     Document Type: Article

References (56)

1. Crayston, J. A.; Devine, J. N.; Walton, J. C. Tetrahedron 2000, 56, 7829.
2. (a) Dougherty, D. A. Acc. Chem. Res. 1991, 24. 88.
3. (b) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346.
4. (c) Rajca, A. Chem. Rev. 1994, 94, 871.
5. Ito, A.; Urabe, M.; Tanaka, K. Polyhedron 2003, 22, 1829 and references therin.
6. (a) Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1992, 114, 7470.
7. (b) Rajca, S.; Rajca, A. J. Am. Chem. Soc. 1995, 117, 9172.
8. (c) Nakamura, T.; Momose, T.; Shida, T.; Kinoshita, T.; Takui, T.; Teki, Y.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 11292.
9. (d) Nakamura, T.; Momose, T.; Shida, T.; Sato, K.; Nakazawa, S.; Kinoshita, T.; Takui, T.; Itoh, K.; Okuno, T.; Izuoka, A.; Sugawara, T. J. Am. Chem. Soc. 1996, 118, 8684.
10. (e) Sedó, J.; Ruiz, D.; Vidal-Gancedo, J.; Rovira, C.; Bonvoisin, J.; Launay, J.-P.; Veciana, J. Adv. Mater. 1996, 8, 748.
11. (a) Matsushita, M.; Nakamura, T.; Momose, T.; Shida, T.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K. Bull. Chem. Soc. Jpn. 1993, 66, 1333.
12. (b) Izuoka, A.; Hiraishi, M.; Abe, T.; Sugawara, T.; Sato, K.; Takui, T. J. Am. Chem. Soc. 2000, 122, 3234.
13. (c) Nakazaki, J.; Chung, I.; Matsushita, M. M.; Sugawara, T.; Watanabe, R.; Izuoka, A.; Kawada, Y. J. Mater. Chem. 2003, 13, 1011.
14. (d) Harada, G.; Jin, T.; Izuoka, A.; Matsushita, M. M.; Sugawara, T. Tetrahedron Lett. 2003, 44, 4415.
15. (a) Nelsen, S. F. Chem.-Eur. J. 2000, 6, 581.
16. (b) Launay, L.-P. Chem. Soc. Rev. 2001, 30, 386.
17. (a) Mazur, S.; Schroeder, A. H. J. Am. Chem. Soc. 1978, 100, 7339.
18. (b) Nelsen, S. R; Thomson-Colon, J. A.; Katfory, M. J. Am. Chem. Soc. 1989, 111, 2809.
19. (c) Almlöf, J. E.; Feyereisen, M. W.; Josefiak, T. H.; Miller, L. L. J. Am. Chem. Soc. 1990, 112, 1206.
20. (d) Maslak, P.; Augustine, M. P.; Burkey, J. D. J. Am. Chem. Soc. 1990, 112, 5359.
21. (e) Utamapanya, S.; Rajca, A. J. Am. Chem. Soc. 1991, 113, 9242.
22. (f) Telo, J. P.; Shohoji, M. C. B. L.; Herold, B. J.; Grampp, G. J. Chem. Soc., Faraday Trans. 1992, 88, 47.
23. (g) Bonvoisin, J.; Launay, J.-P.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1994, 98, 5052.
24. (h) Lahil, K.; Moradpour, A.; Bowlas, C.; Menou, F.; Cassoux, P.; Bonvoisin, J.; Launay, J.-P.; Dive, G.; Dehareng, D. J. Am. Chem. Soc. 1995, 117, 9995.
25. (i) Bonboisin, J.; Launay, J.-P.; Verbouwe, W.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1996, 100, 17079.
26. (j) Nelsen, S. F.; Tran, H. Q.; Nagy, M. A. J. Am. Chem. Soc. 1998, 120, 298.
27. (k) Lambert, C.; Gaschler, W.; Schmälzlin, E.; Meerholz, K.; Bräuchle, C. J. Chem. Soc., Perkin Trans 2 1999, 577.
28. (l) Rovira, C.; Ruiz-Molina, D.; Elsner, O.; Vidal-Gancedo, J.; Bonvoisin, J.; Launay, J.-P.; Veciana, J. Chem.-Eur. J. 2001, 7, 240.
29. (m) Mayor, M.; Büschel, M.; Fromm, K. M.; Lehn, J.-M.; Daub, J. Chem.-Eur. J. 2001, 7, 1266.
30. (n) Lambert, C.; Nöll, G.; Hampel, F. J. Phys. Chem. A 2001, 105, 7751.
31. (o) Lindeman, S. V.; Rosokha, S. V.; Sun, D.; Kochi, J. K. J. Am. Chem. Soc. 2002, 124, 842.
32. (p) Lambert, C.; Nöll, G. Chem.-Eur. J. 2002, 8, 3467.
33. (q) Dumur, F.; Gautier, N.; Gallego-Planas, N.; Sahin, Y.; Levillain, E.; Masino, M.; Girlando, A.; Lloveras, V.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C. J. Org. Chem. 2004, 69, 2164.
34. (a) Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434.
35. (b) Lambert, C.; Nöll, G.; Schelter, J. Nat. Mater. 2002, 1, 69.
36. (c) Lambert, C.; Nöll, G. J. Chem. Soc., Perkin Trans. 2 2002, 2039.
37. Ishida, T.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 4238.
38. Nishiumi, T.; Nomura, Y.; Chimoto, Y.; Higuchi, M.; Yamamoto, K. J. Phys. Chem. B 2004, 108, 7992.
39. The temperature dependence of magnetic susceptibility for 1 was analyzed by the modified Bleaney-Bowers equation for singlet-triplet model. Bleaney, B.; Bowers, K. D. Proc. R. Soc., London Ser. A 1952, 214, 451.
40. i symmetrical constraint. All the calculations were done with the Gaussian 98 program package.
41. o) for the doublet species; √2 for S = I, √3 and 2 for 5 = 3/2. For determination of spin multiplicity for high-spin molecules by using the pulsed ESR technique, see: (a) Isoya, J.; Kanda, H.; Norris, J. R.; Tang, J.; Brown, M. K. Phys. Rev. B 1990, 41, 3905.
42. (b) Astashkin, A. V.; Schweiger, A. Chem. Phys. Lett. 1990, 174, 595.
43. (c) Sato, K.; Yano, M.; Furuichi, M.; Shiomi, D.; Takui, T.; Abe, K.; Itoh, K.; Higuchi, A.; Katsuma, K.; Shirota, Y. J. Am. Chem. Soc. 1997, 119, 6607.
44. (d) Ito, A.; Ino, H.; Matsui, Y.; Hirao, Y.; Tanaka, K.; Kanemoto, K.; Kato, T. J. Phys. Chem. A 2004, 108, 5715.
45. Robin, M.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247.
46. (a) Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391.
47. (b) Hush, N. S. Electrochem. Acta 1968, 13, 1005.
48. (c) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
49. (d) Hush, N. S. Coord. Chem. Rev. 1985, 64, 135.
50. Bailey, S. E.; Zink, J. I.; Nelsen, S. F. J. Am. Chem. Soc. 2003, 125, 5939.
51. Nelsen, S. F.; Konradsson, A. E.; Weaver, M. N.; Telo, J. P. J. Am. Chem. Soc. 2003, 125, 12493.
52. Szeghalmi, A. V.; Erdmann, M.; Engel, V.; Schmitt, M.; Amthor, S.; Kriegisch, V.; Nöll, G.; Stahl, R.; Lambert, C.; Leusser, D.; Stalke, D.; Zabel, M.; Popp, J. J. Am. Chem. Soc. 2004, 126, 7834.
53. Nelsen, S. F.; Weaver, M. N.; Zink, J. I.; Telo, J. P. J. Am. Chem. Soc. 2005, 127, 10611.
54. Nelsen, S. F.; Weaver, M. N.; Telo, J. P.; Lucht, B. L.; Barlow, S. J. Org. Chem. 2005, 70, 9326.
55. (a) Hoijtink, G. J.; Weijland, W. P. Recl. Trav. Chim. Pays-Bas 1957, 76, 836.
56. (b) Buschow, K. J. J.; Dieleman, J.; Hoijtink, G. J. Mol. Phys. 1963-1964, 7, 1.