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

(Note: The full text of this document is currently only available in the PDF Version )

Akihiro Ito, Takeshi Saito, Ken-ichi Ota, Takeshi Miura, Yohji Misaki, Kazuyoshi Tanaka and Tokio Yamabe


Abstract

A novel dimer model for poly(m-aniline), two amino groups of which are effectively shielded by surrounding nitro groups, has been prepared in good yield and characterised by X-ray crystallographic, electrochemical and EPR studies. A 2:1 weak charge transfer complex with tetracyano-p-quinodimethane has been prepared and showed a moderate electrical conductivity (sigma;rt=1.3103 Scm1) in the single crystalline form. The X-ray crystal structure of the complex has also been examined in connection with the electrical conductivity.


References

  1. A. Rajca, Chem. Rev., 1994, 94, 871 CrossRef CAS 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 Search PubMed.
  3. K. Yoshizawa, K. Tanaka and T. Yamabe, Chem. Lett., 1990, 1331; K. Yoshizawa, K. Tanaka, T. Yamabe and J. Yamauchi, J. Chem. Phys., 1992, 96, 5516 CrossRef CAS; K. Yoshizawa, A. Chano, A. Ito, K. Tanaka, T. Yamabe, H. Fujita, J. Yamauchi and M. Shiro, J. Am. Chem. Soc., 1992, 114, 5994 CrossRef CAS; A. Ito, T. Saito, K. Tanaka and T. Yamabe, Tetrahedron Lett., 1995, 48, 8890; K. Yoshizawa, M. Hatanaka, H. Ago, K. Tanaka and T. Yamabe, Bull. Chem. Soc. Jpn., 1996, 69, 1417 CAS.
  4. K. Yoshizawa, A. Takata, K. Tanaka and T. Yamabe, Polym. J., 1992, 24, 857 Search PubMed; K. Yoshizawa and R. Hoffmann, Chem. Eur. J., 1995, 1, 403 CAS.
  5. H. Fukutome, I. Takahashi and M. Ozaki, Chem. Phys. Lett., 1987, 133, 34 CrossRef CAS; D. A. Kaisaki, W. Chang and D. A. Dougherty, J. Am. Chem. Soc., 1991, 113, 2764 CrossRef CAS; K. Tanaka, H. Ago and T. Yamabe, Synth. Met., 1995, 72, 225 CrossRef CAS.
  6. K. Yoshizawa, K. Tanaka and T. Yamabe, J. Phys. Chem., 1994, 98, 1851 CrossRef CAS; A. Ito, H. Miyajima, K. Yoshizawa, K. Tanaka and T. Yamabe, J. Org. Chem., 1997, 62, 38 CrossRef CAS.
  7. H. Kobayashi, F. Marumo and Y. Saito, Acta Crystallogr., Sect. B, 1971, 27, 373 CrossRef CAS; A. J. Epstein, S. Etemad, A. F. Garito and A. J. Heeger, Phys. Rev. B, 1972, 5, 952 CrossRef; T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 1163 CrossRef CAS; T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 2474 CrossRef CAS; H. Kobayashi, Bull. Chem. Soc. Jpn., 1973, 46, 2675 CAS; H. Kobayashi, Bull. Chem. Soc. Jpn., 1974, 47, 1346 CAS; R. Somoano, V. Hádek, S. P. S. Yen, A. Rembaum and R. Derk, J. Chem. Phys., 1975, 62, 1061 CrossRef CAS; I. Maki, Y. Matsunaga, M. Nakakura and A. Nonaka, Bull. Chem. Soc. Jpn., 1975, 48, 1368 CAS; H. Kobayashi, Bull. Chem. Soc. Jpn., 1975, 48, 1373 CAS; T. Sundaresan and S. C. Wallwork, Acta Crystallogr., Sect. B, 1972, 28, 3065 CrossRef CAS; D. Chasseau, J. Gaultier and C. Havw, Acta Crystallogr., Sect. B, 1976, 32, 3262 CrossRef; R. C. Wheland and J. L. Gilson, J. Am. Chem. Soc., 1976, 98, 3916 CrossRef CAS; 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 CrossRef.
  8. H. Kusakawa and S. Nishizaki, Bull. Chem. Soc. Jpn., 1965, 38, 313 CAS; J. Honzl, K. Ulbert, V. Hádek and M. Tlustáková, Chem. Commun., 1965, 440 RSC; Y. Matsunaga, Helv. Phys. Acta, 1963, 36, 800 Search PubMed; K. Kan and Y. Matsunaga, Bull. Chem. Soc. Jpn., 1972, 45, 2096 CAS; Y. Matsunaga and Y. Suzuki, Bull. Chem. Soc. Jpn., 1972, 45, 3375 CAS; G. Dix, Phys. Status Solidi, A, 1974, 24, 139 CAS.
  9. F. D. Gunstone and S. H. Tucker, J. Appl. Chem., 1952, 2, 204 Search PubMed.
  10. C. J. Gilmore, MITHRIL, Integrated Direct Methods Computer Program, University of Glasgow, Scotland, 1990.
  11. G. M. Sheldrick, SHELXS 86, Program for the Solution of Crystal Structures, University of Göttingen, 1986; Acta Crystallogr., Sect. A, 1990, 46, 467 Search PubMed.
  12. 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.
  13. Molecular Structure Corporation, TEXSAN 1.8, Crystal Structure Analysis Package, The Woodlands, TX, 1997.
  14. See, e.g., A. Terahara, H. Ohya-Nishiguchi, N. Hirota and A. Oku, J. Phys. Chem., 1986, 90, 1565 Search PubMed.
  15. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997 Search PubMed.
  16. Z. P. Povet'eva, L. A. Chetkina and V. V. Kopylov, Sov. Phys. Crystallogr., 1977, 22, 424 Search PubMed.
  17. A. Ito, K. Ota, K. Yoshizawa, K. Tanaka and T. Yamabe, Chem. Phys. Lett., 1994, 223, 27 CrossRef CAS.
  18. A. Ito, T. Saito, K. Tanaka and T. Yamabe, unpublished work.
  19. F. A. Neugebauer and S. Bamberger, Angew. Chem., 1971, 83, 48.
  20. G. R. Luckhurst, in Spin Labelling. Theory and Applications, ed. L. J. Berliner, Academic Press, New York, 1976, vol. 1, p. 133 Search PubMed.
  21. In spite of our several efforts, complexes with other acceptor molecules than TCNQ have not been obtained; the preparation of TCNQF4(2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) complexes also failed.
  22. R. E. Long, R. A. Sparks and K. N. Trueblood, Acta Crystallogr., 1965, 18, 932 CrossRef CAS.
  23. T. E. Phillips, T. J. Kistenmacher, J. P. Ferraris and D. O. Cowan, J. Chem. Soc., Chem. Commun., 1973, 471 RSC; T. J. Kistenmacher, T. E. Phillips and D. O. Cowan, Acta Crystallogr., Sect. B, 1974, 30, 763 CrossRef CAS.
  24. A. Hoekstra, T. Spoelder and A. Vos, Acta Crystallogr., Sect. B, 1972, 28, 14 CrossRef CAS.
  25. 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 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.