Preparation, X-ray crystal structures and electronic properties of N,N′-bis(2,6-dinitrophenyl)-1,3-phenylenediamine and a complex with tetracyano-p-quinodimethane

Journal of Materials Chemistry

Volumn 8, Issue 8, 1998, Pages 1799-1803

  Ito, Akihiro ^a   Saito, Takeshi ^a   Ota, Ken Ichi ^a   Miura, Takeshi ^a   Misaki, Yohji ^a   Tanaka, Kazuyoshi ^a   Yamabe, Tokio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30844455128     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803379j     Document Type: Article

References (52)

1. A. Rajca, Chem. Rev., 1994, 94, 871 and references therein.
2. A. R. Forrester, J. M. Hay and R. H. Thomson, Organic Chemistry of Stable Free Radicals, Academic Press, New York, 1968.
3. K. Yoshizawa, K. Tanaka and T. Yamabe, Chem. Lett., 1990, 1331;
4. K. Yoshizawa, K. Tanaka, T. Yamabe and J. Yamauchi, J. Chem. Phys., 1992, 96, 5516;
5. K. Yoshizawa, A. Chano, A. Ito, K. Tanaka, T. Yamabe, H. Fujita, J. Yamauchi and M. Shiro, J. Am. Chem. Soc., 1992, 114, 5994;
6. A. Ito, T. Saito, K. Tanaka and T. Yamabe, Tetrahedron Lett., 1995, 48, 8890;
7. K. Yoshizawa, M. Hatanaka, H. Ago, K. Tanaka and T. Yamabe, Bull. Chem. Soc. Jpn., 1996, 69, 1417.
8. K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J., 1992, 24, 857;
9. K. Yoshizawa and R. Hoffmann, Chem. Eur. J., 1995, 1, 403.
10. H. Fukutome, I. Takahashi and M. Ozaki, Chem. Phys. Lett., 1987, 133, 34;
11. D. A. Kaisaki, W. Chang and D. A. Dougherty, J. Am. Chem. Soc., 1991, 113, 2764;
12. K. Tanaka, H. Ago and T. Yamabe, Synth. Met., 1995, 72, 225.
13. K. Yoshizawa, K. Tanaka and T. Yamabe, J. Phys. Chem., 1994, 98, 1851;
14. A. Ito, H. Miyajima, K. Yoshizawa, K. Tanaka and T. Yamabe, J. Org. Chem., 1997, 62, 38.
15. H. Kobayashi, F. Marumo and Y. Saito, Acta Crystallogr., Sect. B, 1971, 27, 373;
16. A. J. Epstein, S. Etemad, A. F. Garito and A. J. Heeger, Phys. Rev. B, 1972, 5, 952;
17. T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 1163;
18. T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 2474;
19. H. Kobayashi, Bull. Chem. Soc. Jpn., 1973, 46, 2675;
20. H. Kobayashi, Bull. Chem. Soc. Jpn., 1974, 47, 1346;
21. R. Somoano, V. Hádek, S. P. S. Yen, A. Rembaum and R. Derk, J. Chem. Phys., 1975, 62, 1061;
22. I. Maki, Y. Matsunaga, M. Nakakura and A. Nonaka, Bull. Chem. Soc. Jpn., 1975, 48, 1368;
23. H. Kobayashi, Bull. Chem. Soc. Jpn., 1975, 48, 1373;
24. T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 3065;
25. D. Chasseau, J. Gaultier and C. Havw, Acta Crystallogr., Sect. B, 1976, 32, 3262;
26. R. C. Wheland and J. L. Gilson, J. Am. Chem. Soc., 1976, 98, 3916;
27. G. J. Ashwell, D. D. Eley, S. C. Wallwork, M. R. Willis, G. F. Peachey and D. B. Wilkos, Acta Crystallogr., Sect. B, 1977, 33, 843.
28. H. Kusakawa and S. Nishizaki, Bull. Chem. Soc. Jpn., 1965, 38, 313;
29. J. Honzl, K. Ulbert, V. Hádek and M. Tlustáková, Chem. Commun., 1965, 440;
30. Y. Matsunaga, Helv. Phys. Acta, 1963, 36, 800;
31. K. Kan and Y. Matsunaga, Bull. Chem. Soc. Jpn., 1972, 45, 2096;
32. Y. Matsunaga and Y. Suzuki, Bull. Chem. Soc. Jpn., 1972, 45, 3375;
33. G. Dix, Phys. Status Solidi, A, 1974, 24, 139.
34. F. D. Gunstone and S. H. Tucker, J. Appl. Chem., 1952, 2, 204.
35. C. J. Gilmore, MITHRIL, Integrated Direct Methods Computer Program, University of Glasgow, Scotland, 1990.
36. G. M. Sheldrick, SHELXS 86, Program for the Solution of Crystal Structures, University of Göttingen, 1986;
37. Acta Crystallogr., Sect. A, 1990, 46, 467.
38. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits and C. Smykalla, DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
39. Molecular Structure Corporation, TEXSAN 1.8, Crystal Structure Analysis Package, The Woodlands, TX, 1997.
40. See, e.g., A. Terahara, H. Ohya-Nishiguchi, N. Hirota and A. Oku, J. Phys. Chem., 1986, 90, 1565.
41. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
42. Z. P. Povet'eva, L. A. Chetkina and V. V. Kopylov, Sov. Phys. Crystallogr., 1977, 22, 424.
43. A. Ito, K. Ota, K. Yoshizawa, K. Tanaka and T. Yamabe, Chem. Phys. Lett., 1994, 223, 27.
44. A. Ito, T. Saito, K. Tanaka and T. Yamabe, unpublished work.
45. F. A. Neugebauer and S. Bamberger, Angew. Chem., 1971, 83, 48.
46. G. R. Luckhurst, in Spin Labelling. Theory and Applications, ed. L. J. Berliner, Academic Press, New York, 1976, vol. 1, p. 133.
47. 4 (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) complexes also failed.
48. R. E. Long, R. A. Sparks and K. N. Trueblood, Acta Crystallogr., 1965, 18, 932.
49. T. E. Phillips, T. J. Kistenmacher, J. P. Ferraris and D. O. Cowan, J. Chem. Soc., Chem. Commun., 1973, 471;
50. T. J. Kistenmacher, T. E. Phillips and D. O. Cowan, Acta Crystallogr., Sect. B, 1974, 30, 763.
51. A. Hoekstra, T. Spoelder and A. Vos, Acta Crystallogr., Sect. B, 1972, 28, 14.
52. J. S. Chappell, A. N. Bloch, W. A. Bryden, M. Maxfield, T. O. Poehler and D. O. Cowan, J. Am. Chem. Soc., 1981, 103, 2442.