Optical and magnetic properties of ionic charge transfer complexes based on 1,2-dicyano[60]fullerene

Journal of Materials Chemistry

Volumn 13, Issue 2, 2003, Pages 252-257

  Yoshida, Yukihiro ^a   Otsuka, Akihiro ^a   Drozdova, Olga O ^a,b,c   Yakushi, Kyuya ^b   Saito, Gunzi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c IOFFE INSTITUTE   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICYANO[60]FULLERENE; FULLERENE DERIVATIVE; POTASSIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; ELECTRON; ELECTRON SPIN RESONANCE; INFRARED SPECTROSCOPY; MAGNETISM; MOLECULAR BIOLOGY; RAMAN SPECTROMETRY; REDUCTION; SYNTHESIS; TEMPERATURE; ULTRAVIOLET SPECTROSCOPY;

EID: 0037323680     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209163a     Document Type: Article

References (76)

1. (a) T. Suzuki, Y. Maruyama, T. Akasaka, W. Ando, K. Kobayashi and S. Nagase, J. Am. Chem. Soc., 1994, 116, 1359;
2. (b) M. Keshavarz K., B. Knight, R. C. Haddon and F. Wudl, Tetrahedron, 1996, 52, 5149;
3. (c) W. T. Ford, T. Nishioka, F. Qiu, F. D'Souza, J. Choi, W. Kutner and K. Noworyta, J. Org. Chem., 1999, 64, 6257.
4. For reviews, see: (a) R. Taylor and D. R. M Walton, Nature, 1993, 363, 685;
5. (b) A. L. Balch and M. M. Olmstead, Chem. Rev., 1998, 98, 2123;
6. (c) N. Martin, L. Sanchez, B. Illescas and I. Perez, Chem. Rev., 1998, 98, 2527;
7. (d) R. Taylor, Lecture Notes on Fullerene Chemistry: A Handbook for Chemists, Imperial College Press, London, 1999.
8. For examples, see: (a) G. Saito, T. Teramoto, A. Otsuka, Y Sugita, T. Ban, M. Kusunoki and K Sakaguchi, Synth. Met., 1994, 64, 359;
9. (b) D. V. Konarev, R. N. Lyubovskaya, N. V. Drichko, E. I. Yudanova, Y. M. Shul'ga, A. L. Litvinov, V. N. Semkin and B. P. Tarasov, J. Mater. Chem., 2000, 10, 803;
10. (c) C. A. Reed and R. D. Bolskar, Chem. Rev., 2000, 100, 1075.
11. 2, o-dichlorobenzene.
12. D. V. Konarev, V. N. Semkin, A. Graja and R. N. Lyubovskaya, J. Mol. Struct., 1998, 450, 11.
13. (a) F. N. Tebbe, R. L. Harlow, D. B. Chase, D. L. Thorn, G. C. Campbell, J. C. Calabrese, N. Herron, R. J. Young and E. Wasserman, Science, 1992, 256, 822;
14. (b) P. R. Birkett, P. B. Hitchcock, H. W. Kroto, R. Taylor and D. R. M. Walton, Nature, 1992, 357, 479;
15. (c) P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1993, 1230.
16. Y. Yoshida, A. Otsuka, O. O. Drozdova and G. Saito, J. Am. Chem. Soc., 2000, 122, 7244.
17. For some 1,2-added methanofullerides, the heterolytic opening of the cyclopropane ring has been reported: (a) M. Eiermann, R. C. Haddon, B. Knight, Q. C. Li, M. Maggini, N. Martín, T. Ohno, M.-Prato, T. Suzuki and F. Wudl, Angew. Chem., Int. Ed. Engl., 1995, 34, 1591;
18. (b) B. Knight, N. Martín, T. Ohno, E. Orti, C. Rovira, J. Veciana, J. Vidal-Gancedo, P. Viruela, R. Viruela and F. Wudl, J. Am. Chem. Soc., 1997, 119, 9871.
19. M. Keshavarz K., B. Knight, G. Srdanov and F. Wudl, J. Am. Chem. Soc., 1995, 117, 11371.
20. Z. Suo, X. Wei, K. Zhou, Y. Zhang, C. Li and Z. Xu, J. Chem. Soc., Dalton Trans., 1998, 3875.
21. Y. Yoshida, A. Otsuka and G. Saito, Mol. Cryst. Liq. Cryst., 2002, 376, 189.
22. D. V. Konarev, S. S. Khasanov, A. Otsuka, Y. Yoshida and G. Saito, J. Am. Chem. Soc., 2002, 124, 7648.
23. P. M. Treichel, G. P. Essenmacher, H. F. Efner and K. J. Klabunde, Inorg. Chim. Acta, 1981, 48, 41.
24. J. Chen, Z.-E. Huang, R.-F. Cai, Q.-F. Shao, S.-M. Chen and H.-J. Ye, J. Chem. Soc., Chem. Commun., 1994, 2177.
25. (a) P. Bhyrappa, P. Paul, J. Stinchcombe, P. D. W. Boyd and C. A. Reed, J. Am. Chem. Soc., 1993, 115, 11004;
26. (b) P. D. W. Boyd, P. Bhyrappa, P. Paul, J. Stinchcombe, R. D. Bolskar, Y. Sun and C. A. Reed, J. Am. Chem. Soc., 1995, 117, 2907.
27. (a) F. N. Tebbe, J. Y. Becker, D. B. Chase, L. E. Firment, E. R. Holler, B. S. Malone, P. J. Krusic and E. Wasserman, J. Am. Chem. Soc., 1991, 113, 9900;
28. (b) P. R. Birkett, R. Taylor, N. K. Wachter, M. Carano, F. Paolucci, S. Roffia and F. Zerbetto, J. Am. Chem. Soc., 2000, 122, 4209.
29. For reviews, see: (a) M. J. Rosseinsky, Chem. Mater., 1998, 10, 2665;
30. (b) D. V. Konarev and R. N. Lyubovskaya, Russ. Chem. Rev., 1999, 68, 19.
31. (a) H. Kuzmany, M. Matus, B. Burger and J. Winter, Adv. Mater., 1994, 6, 731;
32. (b) M. S. Dresselhaus, G. Dresselhaus and P. C. Eklund, J. Raman Spectrosc., 1996, 27, 351.
33. H. P. Fritz, W. Lüttke, H. Stammreich and R. Forneris, Chem. Ber., 1959, 92, 3246.
34. Z. Suo, Y. Zhang, J.-M. Zheng, Z. Xu, C. Li and Z. Bai, Chem. Phys. Lett., 1999, 315, 321.
35. H. Kondo, T. Momose and T. Shida, Chem. Phys. Lett., 1995, 237, 111.
36. (a) M. Baumgarten and L. Gherghel, in Progress in Fullerene Research, eds. H. Kuzmany, J. Fink, M. Mehring and S. Roth, World Scientific, Singapore, 1994, p. 384;
37. (b) V. Brezová, A. Gügel, P. Rapta and A. Staško, J. Phys. Chem., 1996, 100, 16232;
38. (c) A. Staško, V. Brezová, S. Biskupič, K.-P. Dinse, R. Groß, M. Baumgarten, A. Gügel and P. Belik, J. Electroanal. Chem., 1997, 423, 131;
39. (d) V. Brezová, A. Staško, P. Rapta, D. M. Guldi, K.-D. Asmus and K.-P. Dinse, Magn. Reson. Chem., 1997, 35, 795;
40. (e) Y. Sun, T. Drovetskaya, R. D. Boskar, R. Bau, P. D. W. Boyd and C. A. Reed, J. Org. Chem., 1997, 62, 3642;
41. (f) A. Mrzel, A. Omerzu, P. Umek, D. Mihailovic, Z. Jaglicic and Z. Trontelj, Chem. Phys. Lett., 1998, 298, 329;
42. (g) A. Mrzel, P. Umek, P. Cevc, A. Omerzu and D. Mihailovic, Carbon, 1998, 36, 603;
43. (h) K. M. Kadish, X. Gao, E. V. Caemelbecke, T. Hirasaka, T. Suenobu and S. Fukuzumi, J. Phys. Chem. A, 1998, 102, 3898;
44. (i) C. Luo, M. Fujitsuka, C.-H. Huang and O. Ito, J. Phys. Chem. A, 1998, 102, 8716;
45. (j) C. Luo, M. Fujitsuka, C.-H. Huang and O. Ito, Phys. Chem. Chem. Phys., 1999, 1, 2923;
46. (k) K. M. Kadish, X. Gao, E. V. Caemelbecke, T. Suenobu and S. Fukuzumi, J. Phys. Chem. A, 2000, 104, 3878.
47. R. D. Bolskar, S. H. Gallagher, R. S. Armstrong, P. A. Lay and C. A. Reed, Chem. Phys. Lett., 1995, 247, 57.
48. (a) K. Nakasuji, Pure Appl. Chem., 1990, 62, 477;
49. (b) S. Horiuchi, H. Yamochi, G. Saito, K. Sakaguchi and M. Kusunoki, J. Am. Chem. Soc., 1996, 118, 8604;
50. (c) G. Saito, H. Sasaki, T. Aoki, Y. Yoshida, A. Otsuka, H. Yamochi, O. O. Drozdova, K. Yakushi, H. Kitagawa and T. Mitani, J. Mater. Chem., 2002, 12, 1640.
51. (a) T. Kato, T. Kodama, M. Oyama, S. Okazaki, T. Shida, T. Nakagawa, Y. Mastui, S. Suzuki, H. Shiromaru, K. Yamauchi and Y. Achiba, Chem. Phys. Lett., 1991, 186, 35;
52. (b) M. A. Greaney and S. M. Gorun, J. Phys. Chem., 1991, 95, 7142.
53. (a) A. J. Schell-Sorokin, F. Mehran, G. R. Eaton, S. S. Eaton, A. Viehbeck, T. R. O'Toole and C. A. Brown, Chem. Phys. Lett., 1992, 195, 225;
54. (b) D. Dubois, M. T. Jones and K. M. Kadish, J. Am. Chem. Soc., 1992, 114, 6446;
55. (c) M. Ruebsam, K.-P. Dinse, M. Plueschau, J. Fink, W. Kraetschmer, K. Fostiropoulos and C. Taliani, J. Am. Chem. Soc., 1992, 114, 10059;
56. (a) Y. Zhou, B. E. Bowler, G. R. Eaton and S. S. Eaton, J. Magn. Reson., 1999, 139, 165;
57. (e) S. Fukuzumi, H. Mori, T. Suenobu, H. Imahori, X. Gao and K. M. Kadish, J. Phys. Chem. A, 2000, 104, 10688.
58. G. Völkel, A. Pöppl, J. Simon, J. Hoentsch, S. Orlinskii, H. Klos and B. Gotschy, Phys. Rev., 1995, B52, 10188.
59. (a) P. Venturini, V. Krasevec, D. Mihailovic, M. Eiermann, G. Srdanov, N. S. Sariciftci, C. Li and F. Wudl, in Progress in Fullerene Research, eds. H. Kuzmany, J. Fink, M. Mehring and S. Roth, World Scientific, Singapore, 1994, p. 514;
60. (b) M. T. Jones, K. M. Kadish, R. Subramanian, P. Boulas and M. N. Vijayashree, Synth. Met., 1995, 70, 1341;
61. (c) M. Iyoda, S. Sasaki, F. Sultana, M. Yoshida, Y. Kuwatani and S. Nagase, Tetrahedron Lett., 1996, 37, 7987;
62. (d) S. Fukuzumi, T. Suenobu, X. Gao and K. M. Kadish, J. Phys. Chem. A, 2000, 104, 2908.
63. (a) R. Prins and F. J. Reinders, Chem. Phys. Lett., 1969, 3, 45;
64. (b) C. Elschenbroich, E. Bilger and J. Koch, J. Am. Chem. Soc., 1984, 106, 4297.
65. (a) Q. Zhu, D. E. Cox and J. E. Fischer, Phys. Rev. B: Condens. Matter, 1995, 51, 3966;
66. (b) P. Petit, J. Robert and J. E. Fischer, Phys. Rev. B: Condens. Matter, 1995, 51, 11924;
67. (c) G. Oszlányi, G. Bortel, G. Faigel, M. Tegze, L. Gránásy, S. Pekker, P. W. Stephens, G. Bendele, R. Dinnebier, G. Mihály, A. Jánossy, O. Chauvet and L. Forró, Phys. Rev. B: Condens. Matter, 1995, 51, 12228;
68. (d) G. Oszlányi, G. Bortel, G. Faigel, L. Gránásy, G. M. Bendele, P. W. Stephens and L. Forró, Phys. Rev. B: Condens. Matter, 1996, 54, 11849.
69. W. E. Broderick, K. W. Choi and W. C. Wan, Proc. Etectrochem. Soc., 1997, 97-14, 1102.
70. D. V. Konarev, S. S. Khasanov, A. Otsuka and G. Saito, J. Am. Chem. Soc., 2002, 124, 8520.
71. D. V. Konarev, S. S. Khasanov, I. I. Vorontsov, G. Saito, M. Yu. Antipin, A. Otsuka and R. N. Lyubovskaya, Chem. Commun., 2002, 2548.
72. (a) R. Tycko, G. Dabbagh, R. M. Fleming, R. C. Haddon, A. V. Makhija and S. M. Zahurak, Phys. Rev. Lett., 1991, 67, 1886;
73. (b) W. I. F. David, R. M. Ibberson, T. J. S. Dennis, J. P. Hare and K. Prassides, Europhys. Lett., 1992, 18, 219.
74. (a) J. A. Pople and F. E. Karasz, J. Phys. Chem. Solids, 1961, 18, 28;
75. (b) F. E. Karasz and J. A. Pople, J. Phys. Chem. Solids, 1961, 20, 294.
76. Y. Yoshida, A. Otsuka, D. V. Konarev and G. Saito, Synth. Met., in press.