Hydrogen-bonded organic ferromagnet

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4369-4379

  Matsushita, Michio M ^a   Izuoka, Akira ^a   Sugawara, Tadashi ^a   Kobayashi, Tatsuya ^a   Wada, Nobuo ^a   Takeda, Naoya ^a   Ishikawa, Masayasu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FERROMAGNETIC MATERIAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROGEN BOND; MAGNET; MATERIALS; STRUCTURE ANALYSIS;

EID: 0030908878     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964083o     Document Type: Article

References (55)

1. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
2. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
3. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
4. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
5. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
6. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
7. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
8. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
9. For a recent overview, see: Miller, J. S., Dougherty, D. A., Eds. Mol. Cryst. Liq. Cryst. 1989, 176, 1-562. Advanced Organic Solid State Materials; Chiang, L. Y., Chaikin, P. M., Cowan, D. O., Eds.; Materials Research Society: Pittsburgh, PA, 1989; pp 3-92. Molecular Magnetic Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio, F., Eds.; Kiuwer Academic: Dordrecht, 1991; Vol. A198. Iwamura, H., Miller, J. S., Eds., Mol. Cryst. Liq. Cryst. 1993, 232/233, 1-360/1-366. Miller, J. S., Epstein, A. J., Eds. Mol. Cryst. Liq. Cryst. 1995, 272-274. Kollmar, C.; Kahn, O. Acc. Chem. Res. 1993, 26, 259. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385. Rajca, A. Chem. Rev. 1994, 94, 871-893. Izuoka, A.; Kumai, R.; Sugawara, T. Adv. Mater. 1995, 7, 672.
10. (a) Kinoshita, M.; Turek, P.; Tamura, M.; Nozawa, K.; Shiomi, D.; Nakazawa, Y.; Ishikawa, M.; Takahashi, M.; Awaga, K.; Inabe, T.; Maruyama, Y. Chem. Lett. 1991, 1225.
11. (b) Nakazawa, Y.; Tamura, M.; Shirakawa, N.; Shiomi, D.; Takahashi, M.; Kinoshita, M.; Ishikawa, M. Phys. Rev. B: Condens. Matter. 1992, 46, 8906.
12. Chiarelli, R.; Novak, M. A.; Rassat, A.; Tholence, J. L. Nature 1993. 363, 147.
13. Nogami, T.; Ishida, T.; Tsuboi, H.; Yoshikawa, H.; Yamamoto, H.; Yasui, M.; Iwasaki, F.; Iwamura, H.; Takeda, N.; Ishikawa, M. Chem. Lett. 1995, 635-636 and references therein.
14. Le, L. P.; Keren, A.; Luke, G. M.; Wu, W. D.; Uemura, Y. J.; Tamura, M.; Ishikawa, M.; Kinoshita, M. Chem. Phys. Lett. 1993, 206, 405.
15. (a) Zheludev, A.; Bonnet, M.; Ressouche, E.; Schweizer, J.; Wan, M.; Wang, H. J. Magn. Magn. Mater. 1994, 135, 147-160.
16. (b) Zheludev, A.; Ressouche, E.; Schweizer, J.; Turek, P.; Wan, M.; Wang, H. Solid State Commun. 1994, 90, 233-235.
17. McConnell, H. M.; J. Chem. phys. 1963, 39, 1910.
18. (a) Hutchison, C. A., Jr.; Kohler, B. E. J. Chem. Phys. 1969, 51, 3327.
19. (b) Anderson, R. J.; Kohler, B. E. J. Chem. Phys. 1978, 65, 2451.
20. (c) Teki, Y.; Fujita, I.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 11499-11505.
21. Izuoka, A.; Murata, S.; Sugawara, T.; Iwamura, H. J. Am. Chem. Soc. 1987, 109, 2631.
22. (a) Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
23. (b) Etter, M. C. J. Phys. Chem. 1991, 95, 4601-4610.
24. (c) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407.
25. There are some reports about the magnetic interaction through hydrogen bonds in the transition metal complexes, see: Figgis, B. N.; Kucharski, E. S.; Vrtis, M. J. Am. Chem. Soc. 1993, 115, 176-18 and references therein.
26. Sugawara, T.; Matsushita, M. M.; Izuoka, A.; Wada, N.; Takeda, N.; Ishikawa, M. J. Chem. Soc., Chem. Commun. 1994, 1723.
27. (a) Hernàndez, E.; Mas, M.; Molins, E.; Rovira, C.; Veciana, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 882.
28. (b) Cirujeda, J.; Hernàndez, E.; Rovira, C.; Stanger, J. L.; Turek, P.; Veciana, J. J. Mater. Chem. 1995, 5, 243-252.
29. (c) Cirujeda, J.; Ochando, L. E.; Amigó, J. M.; Rovira, C; Ruis, J.; Veciana, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 55.
30. (a) Cirujeda, J.; Mas, M; Molins, E.; Panthou, F. L.; Laugier, J.; Park, J. G.; Paulsen, C; Rey, P.; Rovira, C.; Veciana, J. J. Chem. Soc., Chem. Commun. 1995, 709.
31. (b) Cirujeda, J.; Hernàndez, E.; Panthou, F. L.; Laugier, J.; Mas, M.; Molins, E.; Rovira, C; Novoa, J. J.; Rey, P.; Veciana, J. Mol. Cryst. Liq. Cryst. 1995, 271, 1-12.
32. Matsushita, M. M.; Izuoica, A.; Sugawara, T. Mol. Cryst. Liq. Cryst. 1996, 279, 139-144.
33. The crystal structure and the magnetic property of RSNN have been reported briefly by Veciana et al. See ref 14.
34. Neely, J. W.; Hatch, G. F.; Kreilick, R. W. J. Am. Chem. Soc. 1974, 96, 652-656.
35. D'Anna, J. A.; Wharton, J. H. J. chem. Phys. 1970, 53, 4047-4502.
36. Zheludev, A.; Barone, V.; Bonnet, M.; Delley, B.; Grand, A.; Ressouche, E.; Key, P.; Subra, R.; Schweizer, J.; J. Am. Chem. Soc. 1994, 116, 2019.
37. Yaamaguchi, K.; Okumura, M.; Nakano, M. Chem Phys, Lett. 1992, 91, 237.
38. 2 θ relation. It falls to -0.04 at 90° crossing zero at around 60°. According to this result, both the hydrogen and the oxygen atoms of the hydroxy group have the same sign of spin densities as the ipso carbon atom in the dihedral angle range of 0°-60°. Such a result does not conflict with the qualitative explanation in the text.
39. Recently, the spin densities on the hydroxy groups of HQNN were determined by the high-resolution solid state NMR experiment. The result is consistent with result which is described in this paper.: Takeda, S.; Maruda, G.; Oda, A.; Yamaguchi, K.; Matsushita, M. M.; Izuoka, A.; Sugawara, Symposium on Molecular Structure, Fukuoka, Japan, 1996, Abstr. 2P3a57, p 312.
40. Oda, A.; Kawakami, T.; Takeda, S.; Mori, W.; Matsushita, M. M.; Izuoka, A.; Sugawara, T.; Yamaguchi, K. Mol. Cryst. Liq. Cryst., in press.
41. Computational studies of the intermolecular magnetic interaction in the hydrogen-bridged nitroxides were performed by Yamaguchi et al., see: Kawakami, T; Takeda, S; Mori, W; Yamaguchi, K. Chem. Phys. Lett. 1996, 261, 129-137 and references therein.
42. Panthou, F. L.; Luneau, D.; Laugier, J.; Key, P. J. Am. Chem. Soc. 1993, 115, 9095.
43. Jongh, L. J.; Miedema, A. R. Adv. Phys. 1974, 23, 1.
44. Ichikawa, M. Acta Crystallogr. 1978, B34, 2074-2080.
45. Byrn, S. R.; Curtin, D. Y.; Paul, I. C. J. Am. Chem. Soc. 1972, 94, 890-898.
46. (a) Osiecki, J. H.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 1078.
47. (b) Ullman, E. F.; Osiecki, J. H.; Boocock, D. G. B.; Darcy, R. J. Am. Chem. Soc. 1972, 94, 7049.
48. Lamchen, M.; Mittag, T. W. J. Chem. Soc. C 1966, 2300.
49. Fan, H.; Qian, J.; Yao, J.; Zheng, C.; Hao, Q. Acta Crystallogr., Sect. A 1988, 44, 691.
50. Sheldrick, G. M. Crystallographic Computing 3; Sheldrick, G. M.; Kruger, C., Goddard, R., Eds. Oxford University Press: Oxford, U.K., 1985; P 175.
51. Sakurai, T.; Kobayashi, K. Rep. Inst. Phys. Chem. Res. (Tokyo) 1979, 55, 69.
52. Ishikawa, M.; Nakazawa, Y.; Takabatake, T.; Kishi, A.; Kato, R.; Maesono, A. Solid State Commun. 1988, 66, 201.
53. ac measurement in ref 12 must be corrected to 10 mT.
54. Ishikawa, M.; Muller, J. Solid State Commun. 1978, 27, 761.
55. The crystal structures in this paper are drawn by Moldraw: Molecular graphics for Machintosh: Cense, J.-M. Tetrahedron Comput. Methodol. 1989, 2, 65-71.