Syntheses and Properties of Metal Containing Polyimides Based on the Gold Carbene Complex

  • Turgay Seckin
  • Süleyman Koytepe
  • Ismail Ozdemir
  • Bekir Çetinkaya
Article

Abstract

A novel gold carbene complex, bis(1,3-di-p-dimethylaminobenzylimidazolidinylidene) gold(I), was synthesized and polymerized to polyimides in a one-step method with various aromatic dianhyrides. The gold-coordinated polyimides are characterized by IR and NMR (1H, 13C) spectroscopy. The materials have inherent viscosities that range from 1.88 to 2.39 dl/g and show excellent solubility in N-methylpyrrolidone and N,N-dimethylacetamide. The glass transition temperatures of the coordinated polyimides range from 203–265°C and a 5% weight loss in air is observed from 535–578°C. The polymers form dark yellow, tough films that are transparent above 365 nm. The effect of different flexible units on the properties of the polyimides is discussed.

Polyimide gold(I) coordinated polyimides organometallic polymer carbene complexes 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    K. L. Mittal, Polyimides: Synthesis, Characterization and Applications (Plenum, New York, 1984), Vols. 1 & 2.Google Scholar
  2. 2.
    M. K. Ghosh, and K. L. Mittal, eds., Polyimides: Fundamentals and Applications (Marcel Dekker, New York, 1996).Google Scholar
  3. 3.
    D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, eds., Polyimides (Blackie and Son Ltd., Glasgow, 1990).Google Scholar
  4. 4.
    M. Sato, Handbook of Thermoplastics (Marcel Dekker, New York, 1997), p. 665.Google Scholar
  5. 5.
    T. Takekoshi, in Polyimides: Fundamentals and Applications, M. K. Ghosh, and K. L. Mittal, eds. (Wiley, 1996), 7 Chapters 1-3.Google Scholar
  6. 6.
    T. L. St. Clair, in Polyimides, D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, eds. (Blackie and Son Ltd., Glasgow, 1990), Chapt. 3.Google Scholar
  7. 7.
    C. Feger, M. M. Khojasteh, and J. E. McGrath, eds., Polyimides: Materials, Chemistry and Characterization (Elsevier, Amsterdam, 1989).Google Scholar
  8. 8.
    C. E. Sroog, Polyimides, in Encyclopedia of Polymer Science and Technology, F. Mark, N. G. Gaylord, N. M. Bikales, eds. (Interscience, New York, 1969), Vol. 11.Google Scholar
  9. 9.
    M. T. Bessonov, M. M. Koton, V. V. Kudryavtsev, and L. A. Laius, Polyimides: Thermally Stable Polymers (Consultants Bureau, New York, 1987).Google Scholar
  10. 10.
    K. Weinrotter, R. Vodiunig, C. Feger, M. M. Khojasteh, and J. E. McGrath, eds., Polyimides: Materials, Chemistry and Characterization (Elsevier, Amsterdam, 1989).Google Scholar
  11. 11.
    M. J. M. Abadie and B. Sillion, Polyimides and Other High-Temperature Polymers (Elsevier, Amsterdam, 1991).Google Scholar
  12. 12.
    G. C. Davis, B. A. Weath, and G. Gildenblat, in Polyimides: Synthesis, Characterization and Applications, K. L. Mittal, ed. (Plenum Press, New York, 1984), Vol. 2.Google Scholar
  13. 13.
    C. E. Sroog, in Polyimides, D. Wilson, H. D. Stenzenberger, and P. M. Hergenrother, eds. (Blackie, Glasgow, 1990), Chapt. 9.Google Scholar
  14. 14.
    P. E. Cassidy, Thermally Stable Polymers (Marcel Dekker, New York, 1980).Google Scholar
  15. 15.
    M. Marek, Jr., D. Doskocilová, P. Schmidt, B. Schneider, J. Kriz, J. Labsk, and R. Puffr, Polymer 35, 4881(1994).Google Scholar
  16. 16.
    D. B. Strong, High Performance and Engineering Thermoplastic Composites (Technomic Publishers, Lancaster, PA, 1993).Google Scholar
  17. 17.
    Y. Kawashima, T. Ikeda, and H. Kitagawa, Polyimides, Proceedings 3rd International Symposium (Ellenville, 1988).Google Scholar
  18. 18.
    M. K. Gerber, J. R. Pratt, and T. L. St. Clair, Polyimides, Proceedings 3rd International Symposium (Ellenville, 1988).Google Scholar
  19. 19.
    I. Ozdemir, B. çetinkaya, T. Seçkin, and S. Köytepe, J. Mol. Cat. A: Chem. 179, 263(2002).Google Scholar
  20. 20.
    K. Yamanaka, M. Jikei, and M. Kakimoto, Macromolecules 34, 3910(2001).Google Scholar
  21. 21.
    X. Q. Liu, M. Jikei, and M. Kakimoto, Macromolecules 34, 3146(2001).Google Scholar
  22. 22.
    M. T. Lee and G. S. Ferguson, Langmuir 17, 762(2001).Google Scholar
  23. 23.
    X. Q. Liu, K. Yamanaka, M. Jikei, and M. Kakimoto, Chem. Mater. 12, 3885(2000).Google Scholar
  24. 24.
    T. P. Bender and Z. Y. Wang, Macromolecules 33, 9477(2000).Google Scholar
  25. 25.
    H. L. Tyan, C. M. Leu, and K. H. Wei, Chem. Mater. 13, 222(2001).Google Scholar
  26. 26.
    H. Yim, M. D. Foster, J. Engelking, H. Menzel, and A. M. Ritcey, Langmuir 16, 9792(2000).Google Scholar
  27. 27.
    K. Yamanaka, M. Jikei, and M. Kakimoto, Macromolecules 33, 6937(2000).Google Scholar
  28. 28.
    M. Oh-e, S. C. Hong, and Y. R. Shen, J. Phys. Chem. B 104, 7455(2000).Google Scholar
  29. 29.
    J. Fang, H. Kita, and K. Okamoto, Macromolecules 33, 4639(2000).Google Scholar
  30. 30.
    Y. Cai, Macromolecules 29, 535(1996).Google Scholar
  31. 31.
    K. Yamanaka, M. Jikei, and M. Kakimoto, Macromolecules 34, 3910(2001).Google Scholar
  32. 32.
    N. Y. Wai, X. Gong, and K. W. Chan, Chem. Mater. 11, 1165(1999).Google Scholar
  33. 33.
    W. A. Herrmann and G. Gerstberger, Organometallics 16, 2209(1997).Google Scholar
  34. 34.
    W. A. Herrmann, M. Elisin, and J. Fischer, Chem. Eur. J. 2, 772(1996).Google Scholar
  35. 35.
    B. çetinkaya, I. özdemir, C. Bruneau, and P. H. Dixneuf, J. Mol. Cat. A: Chem. 118, L1(1997).Google Scholar
  36. 36.
    B. çetinkaya and I. özdemir, J. Organomet. Chem. 534, 153(1997).Google Scholar
  37. 37.
    I. özdemir, B. Yigit, and B. çetinkaya, J. Organomet. Chem. 633, 27(2001).Google Scholar
  38. 38.
    W. A. Herrmann and B. E. Cornils, Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 12 (VCH, Weinheim, Germany, 1996).Google Scholar
  39. 39.
    W. A. Herrmann and C. P. Reisinger, J. Organomet. Chem. 557, 93(1998).Google Scholar
  40. 40.
    D. Enders, H. Gielen, G. Raabe, and J. Runsink, Chem, Ber. 129, 1483(1996).Google Scholar
  41. 41.
    D. S. Mc Guinness and K. J. Cavel, Organometallics 18, 1596(1999).Google Scholar
  42. 42.
    G. J. Hutchings, Catal. Today 11, 1(2002).Google Scholar
  43. 43.
    H. Ito, T. Yajima, J. Tateiwa, and A. Hosomi, Chem. Commun. 981(2000).Google Scholar
  44. 44.
    A. Wolf and F. Schüth, Appl. Catal. A: General 226, 1(2002).Google Scholar
  45. 45.
    T. Seckin, E. çetinkaya, and S. Koytepe, unpublished results.Google Scholar
  46. 46.
    R. H. Vora, S. H. Goh, and T. S. Chung, Polym. Eng. Sci. 40, 1318(2000).Google Scholar
  47. 47.
    T. L. Grubb, V. L. Ulery, T. J. Smith, G. L. Tullos, H. Yagci, L. J. Mathias, and M. Langsam, Polymer 40, 4279(1999).Google Scholar
  48. 48.
    D. J. Liaw and B. Y. Liaw, Polymer 40, 3183(1999).Google Scholar

Copyright information

© Plenum Publishing Corporation 2003

Authors and Affiliations

  • Turgay Seckin
    • 1
  • Süleyman Koytepe
    • 1
  • Ismail Ozdemir
    • 1
  • Bekir Çetinkaya
    • 2
  1. 1.Chemistry DepartmentInonu UniversityMalatyaTurkey
  2. 2.Faculty of Science, Chemistry DepartmentEge UniversityIzmirTurkey

Personalised recommendations