Polymeric malondialdehyde dianils—a novel type of electrically conducting polymers

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

Rudolf Gompper, Thomas J. J. Müller and Kurt Polborn


Abstract

The reaction of vinamidinium salts withpara-substituted aromatic diamines gives rise to polymeric 2-aryl malonaldehyde dianils in good yields. Polymeric cyanines can be obtained from tetramethoxypropane and a pentamethine cyanine, respectively, and para-substituted aromatic diamines. The degree of polymerisation Pn (n=10–40) was estimated by measuring the intrinsic viscosity η. The polymers show high electrical powder conductivities (σ=0.03–50 S cm–1) after doping with iodine or FeCl3 .


References

  1. Conjugated Polymers and Related Materials, ed. W. R. Salaneck, I. Lundström and B. Ranby, Oxford University Press, Oxford, 1993 Search PubMed.
  2. (a) H. Shirakawa, E. J. Louis, A. G. MacDiarmid, C. K. Chiang and A. J. Heeger, J. Chem. Soc., Chem. Commun., 1977, 578 RSC; (b) C. K. Chiang, Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis and A. G. MacDiarmid, J. Chem. Phys., 1978, 69, 5098 CrossRef CAS; (c) C. K. Chiang, C. R. Fincher, Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis and A. G. MacDiarmid, Phys. Rev. Lett., 1977, 39, 1098 CrossRef CAS; (d) H. Naarmann and N. Theophilou, Synth. Met., 1987, 22, 1 CAS; (e) H. Naarmann, Adv. Mater., 1990, 2, 345 CAS; (f) T. Schimmel, G. Denninger, W. Riess, J. Voit, M. Schwoerer, W. Schoepe and H. Naarmann, Synth. Met., 1989, 28, D11 CrossRef CAS.
  3. (a) A. F. Diaz and J. A. Logan, J. Elektroanal. Chem., 1980, 111, 111 Search PubMed; (b) W.-S. Huang, B. D. Humphrey and A. G. MacDiarmid, J. Chem. Soc., Faraday Trans., 1, 1986, 82, 2385 RSC.
  4. D. M. Ivory, G. G. Miller, J. M. Sowa, L. W. Shacklette, R. R. Chance and R. H. Baugham, J. Chem. Phys., 1979, 71, 1506 CrossRef CAS.
  5. (a) G. Tourillon and F. Garnier, J. Elektroanal. Chem., 1981, 135, 173 Search PubMed; (b) P. Bäuerle, Adv. Mater., 1993, 5, 879; (c) R. D. McCullough, Adv. Mater., 1998, 10, 93 CrossRef CAS.
  6. (a) G. Wegner, Angew. Chem., 1981, 93, 352 CAS; Angew. Chem., Int. Ed. Engl., 1981, 20, 361 Search PubMed; (b) K. Menke and S. Roth, Chem. Unserer Zeit, 1986, 20, 1 Search PubMed; (c) K. Menke and S. Roth, Chem. Unserer Zeit, 1986, 20, 33 Search PubMed; (d) E. P. Goodings, Chem. Soc. Rev., 1976, 5, 95 RSC; (e) A. C. Patil, A. J. Heeger and F. Wudl, Chem. Rev., 1988, 88, 183 CrossRef CAS.
  7. R. E. Peierls, Quantum Theory of Solids, Clarendon, Oxford, 1964 Search PubMed.
  8. S. Roth and M. Filzmoser, Adv. Mater., 1990, 2, 356 CAS.
  9. (a) S. Dähne, Z. Chem., 1965, 5, 441; (b) S. Dähne and D. Leupold, Angew. Chem., 1966, 78, 1029; Angew. Chem., Int. Ed. Engl., 1966, 5, 984 Search PubMed; (c) S. Dähne and S. Kulpe, Structural principles of unsaturated organic compounds, Abh. Akad. Wiss. DDR Nr. 8, Akademie Verlag, Berlin 1977 Search PubMed; (d) S. Dähne, Science, 1978, 199, 1163; (e) S. Dähne and S. Kulpe, J. Prakt. Chem., 1978, 320, 395 CrossRef; (f) M. Klessinger, Chem. Unserer Zeit, 1978, 12, 1 Search PubMed.
  10. (a) J. H. Perlstein, Angew. Chem., 1977, 89, 534 CAS; Angew. Chem., Int. Ed. Engl., 1977, 16, 519 Search PubMed; (b) U. Maier, Top. Curr. Chem., 1976, 61, 85.
  11. T. J. J. Müller, Ph. D. Thesis, Universität München, 1992.
  12. (a) J. S. Miller, Adv. Mater., 1990, 2, 98 CrossRef; (b) J. S. Miller, Adv. Mater., 1990, 2, 378 CrossRef; (c) J. S. Miller, Adv. Mater., 1990, 2, 495 CAS; (d) J. S. Miller, Adv. Mater., 1990, 2, 601 CrossRef; (e) J. M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1986, 83, 5355 CAS; (f) F. Effenberger, H. Schlosser, P. Bäuerle, H. C. Wolf, S. Maier and H. Port, Angew. Chem., 1988, 100, 247; Angew. Chem., Int. Ed. Engl., 1988, 27, 281 Search PubMed; (g) F. L. Carter, Molecular Electronic Devices, Marcel Dekker, New York, 1982, p. 51 Search PubMed; (h) F. Garnier, Angew. Chem., 1989, 101, 529 CAS; Angew. Chem., Int. Ed. Engl., 1989, 28, 513 Search PubMed.
  13. L. Claisen, Ber. Dtsch. Chem. Ges., 1903, 36, 3664 CAS.
  14. (a) N. M. Tsybina, V. G. Vonokurov, T. V. Protopopova and A. P. Skoldinov, J. Gen. Chem., USSR, 1966, 36, 1383; (b) J. E. Parks and R. H. Holm, Inorg. Chem., 1968, 7, 1408 CrossRef CAS; (c) S. C. McGeachin, Can. J. Chem., 1968, 46, 1903 CAS; (d) C. L. Honeybourne and G. A. Webb, Chem. Commun., 1968, 739 RSC; (e) C. L. Honeybourne and G. A. Webb, Chem. Phys. Lett., 1968, 2, 426 CrossRef CAS.
  15. (a) R. Knorr and A. Weiβ, Chem. Ber., 1981, 114, 2104 CAS; (b) R. Knorr, R. Zölch and K. Polborn, Heterocycles, 1995, 40, 559 CAS.
  16. R. Knorr and A. Weiβ, Chem. Ber., 1982, 115, 139 CAS.
  17. K. Feldmann, E. Daltrozzo and G. Scheibe, Z. Naturforsch., 1967, 22b, 722 Search PubMed.
  18. J. Fabian and H. Hartmann, Light Absorption of Organic Colorants, Springer-Verlag, Berlin, 1980, ch. 12 Search PubMed.
  19. J. Kucera and Z. Arnold, Collect. Czech. Chem. Commun., 1967, 32, 1704 CAS.
  20. S. Brownstein, E. J. Gabe and L. Prasad, Can. J. Chem., 1983, 61, 1410 CAS.
  21. Crystal data for 6e: C22H20N2O, M= 328.40, monoclinic, space group P21/c(# 14), a= 9.699(3)Å, b= 35.875(7)Å, c= 10.475(4)Å, α= 90.00(2)°, β= 92.82(2)°, γ= 90.00(2)°, Z= 8, Dc= 1.198 g cm–3, µ= 0.074 mm–1, F(000)= 1392. Data collection: ENRAF-NONIUS CAD4-diffractometer, ω-scan, scan width (0.70 + 0.35 tan Θ°, Θmax= 22.98°, Θmin= 2.03°, crystal dimensions 33 × 47× 53 mm, maximum measuring time 60 s, graphite monochromated Mo-Kα radiation (λ= 0.71069 Å). 5376 measured, 5063 independent reflections, 3871 classed as observed (I > 2σI); refined parameters: 454/0. Solution of structure: SHELXS86, refinement with SHELXS93. Final R1= 0.0632 and wR2= 0.1814 for 2σI; R1= 0.0806 and wR2= 0.1922 for all data; largest/smallest residual electron density ρ= 0.410/– 0.188 e Å–3. The full list of atomic coordinates, bond lengths and angles have been deposited at the Cambridge Crystallographic Data Centre (CCDC). See Information for Authors, J. Mater. Chem., 1998, Issue 1. Any request to the CCDC for this material should quote the full literature citation and the reference number 1145/106 Search PubMed.
  22. Measurements performed by Dr H. Naarmann, BASF AG, Ludwigshafen.
  23. D. Lloyd and H. McNab, Synthesis, 1973, 791 CrossRef CAS.
  24. T. Zincke and W. Würker, Liebigs Ann. Chem., 1905, 338, 121 Search PubMed.
  25. (a) S. Hünig and W. Daum, Chem. Ber., 1955, 88, 1238 CAS; (b) S. Hünig and P. Richters, Chem. Ber., 1958, 91, 442 CAS.
  26. Dr. H. Naarmann, BASF AG, Ludwigshafen, personal communication.
  27. A. Merz and S. Reitmeier, Angew. Chem. Adv. Mater., 1989, 101, 827 Search PubMed; Angew. Chem., Int. Ed. Engl., 1989, 28, 807 Search PubMed.
  28. S. Dähne, B. Bornowski, S. Kulpe, C. Hamann and J. Heim, Ger.(East) DD 244 485 (Cl. H01B1/00) Appl. 194 039, 1987; Chem. Abstr., 1987, 107, P248317a Search PubMed.
  29. C. Jutz, R. Kirchlechner and H.-J. Seidel, Chem. Ber., 1969, 102, 2301 CAS.
  30. D. R. Lloyd, K. S. Tucker and D. R. Marshall, J. Chem. Soc., Perkin Trans. 1, 1981, 726 RSC.
  31. F. Adams, Ph. D. Thesis, Universität München, 1989.
Click here to see how this site uses Cookies. View our privacy policy here.