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Journal of Polymer Research

, Volume 14, Issue 2, pp 147–155 | Cite as

Synthesis and Properties of Noncoplanar Rigid-rod Aromatic Polyamides Containing Phenyl or Naphthyl Substituents

  • Guey-Sheng LiouEmail author
  • Yi-Kai Fang
  • Hung-Ju Yen
Article

Abstract

A series of novel aromatic polyamides having noncoplanar biphenylene units in the main chain and bulky naphthyl or phenyl pendant group at 2,2′-disubstituted position were prepared from the two rigid-rod aromatic dicarboxylic acid monomers, 2,2′-diphenylbiphenyl-4,4′-dicarboxylic acid (1) and 2,2′-dinaphthylbiphenyl-4,4′-dicarboxylic acid (2), and various aromatic diamines. These polyamides were readily soluble in many organic solvents and showed excellent thermal stability associated with high glass-transition temperatures in the range of 229–292°C. These polymers also exhibited strong UV–Vis absorption bands at 262–353 nm in NMP solution, and their photoluminescence spectra showed maximum bands at 440–462 nm in the purple to blue region. The poly(amine–amide) IId derived from the diamine with triphenylamine moieties revealed excellent electrochromic contrast and coloration efficiency, changing color from the pale yellowish neutral form to green then to the blue oxidized forms when scanning potentials positively from 0.00 to 1.30 V.

Figure

Graphical Abstract. A series of novel aromatic polyamides having noncoplanar biphenylene units in the main chain and bulky naphthyl or phenyl pendant group at 2,2′-disubstituted position were prepared from the two dicarboxylic acids and various aromatic diamines. These polyamides were readily soluble in many organic solvents and showed excellent thermal stability associated with high glass-transition temperatures in the range of 229–292°C. These polymers also exhibited strong UV–Vis absorption bands at 262–353 nm in NMP solution, and their photoluminescence spectra showed maximum bands at 440–462 nm in the purple to blue region. The poly(amine–amide) IId derived from the diamine with triphenylamine moieties revealed excellent electrochromic contrast and coloration efficiency, changing color from the pale yellowish neutral form to green then to the blue oxidized forms when scanning potentials positively from 0.00 to 1.30 V.

Key words

polyamides solubility thermal properties noncoplanar electrochemistry 

Notes

Acknowledgment

The authors are grateful to the National Science Council of the Republic of China for financial support of this work.

References

  1. 1.
    D.-J. Liaw, F.-C. Chang, M.-K. Leung, M.-Y. Chou and K. Muellen, Macromolecules, 38, 4024 (2005).CrossRefGoogle Scholar
  2. 2.
    H.-S. Kim, Y.-H. Kim, S.-K. Ahn and S.-K. Kwon, Macromolecules, 36, 2327 (2003).CrossRefGoogle Scholar
  3. 3.
    K.-H. Kim, S. Jang and F.-W. Harris, Macromolecules, 34, 8925 (2001).CrossRefGoogle Scholar
  4. 4.
    S.-H. Lin, F. Li, S. Z. D. Cheng and F.-W. Harris, Macromolecules, 31, 2080 (1998).CrossRefGoogle Scholar
  5. 5.
    K.-C. Chuang, J.-D. Kinder, D. L. Hull, D.-B. McConville and W.-J. Youngs, Macromolecules, 30, 7183 (1997).CrossRefGoogle Scholar
  6. 6.
    C.-P. Yang, S.-H. Hsiao, C.-Y. Tsai and G.-S. Liou, J. Polym. Sci., A, Polym. Chem., 42, 2416 (2004).CrossRefGoogle Scholar
  7. 7.
    S.-H. Hsiao, C.-P. Yang, C.-Y. Tsai and G.-S. Liou, Eur. Polym. J., 40, 1081 (2004).CrossRefGoogle Scholar
  8. 8.
    G.-S. Liou, S.-H. Hsiao and T.-H. Su, J. Mater. Chem., 15, 1812 (2005).CrossRefGoogle Scholar
  9. 9.
    P.-E. Cassidy, Thermally Stable Polymers, Marcel Dekker, New York, 1980.Google Scholar
  10. 10.
    H.-H. Yang, Aromatic High-strength Fibers, Wiley, New York, 1989.Google Scholar
  11. 11.
    D.-J. Liaw and B.-Y. Liaw, Macromol. Symp., 122, 343 (1997).Google Scholar
  12. 12.
    C.-P. Yang, G.-S. Liou, C.-C. Yang and S.-H. Chen, J. Appl. Polym. Sci., 78, 1162 (2000).CrossRefGoogle Scholar
  13. 13.
    D.-J. Liaw, P.-N. Hsu, W.-H. Chen and S.-L. Lin, Macromolecules, 35, 4669 (2002).CrossRefGoogle Scholar
  14. 14.
    G.-S. Liou and S.-H. Hsiao, J. Polym. Sci., A, Polym. Chem., 40, 1781 (2002).CrossRefGoogle Scholar
  15. 15.
    G.-S. Liou, Y.-L. Yang and Y.-O. Su, J. Polym. Sci., A, Polym. Chem., 44, 2587 (2006).CrossRefGoogle Scholar
  16. 16.
    G.-S. Liou, H.-W. Chen and H.-J. Yen, J. Polym. Sci., A, Polym. Chem., 44, 4108 (2006).CrossRefGoogle Scholar
  17. 17.
    G.-S. Liou, H.-W. Chen and H.-J. Yen, Macromol. Chem. Phys., 207, 1589 (2006).CrossRefGoogle Scholar
  18. 18.
    M. Ballauff and G.-F. Schmidt, Macromol. Chem. Rapid. Commun., 8, 93 (1987).CrossRefGoogle Scholar
  19. 19.
    M. Steuer, M. Horth and M. Ballauff, J. Polym. Sci., A, Polym. Chem., 31, 1609 (1993).CrossRefGoogle Scholar
  20. 20.
    L. Cheng and X.-G. Jian, J. Appl. Polym. Sci., 92, 1516 (2004).CrossRefGoogle Scholar
  21. 21.
    G.-S. Liou, S.-H. Hsiao, W.-C. Chen and H.-J. Yen, Macromolecules, 39, 6036 (2006).CrossRefGoogle Scholar
  22. 22.
    G.-S. Liou and H.-J. Yen, J. Polym. Sci., A, Polym. Chem., 44, 6094 (2006).CrossRefGoogle Scholar
  23. 23.
    M. Yamada, T. Matsumoto and T. Kurosaki, Macromolecules, 27, 1117 (1994).CrossRefGoogle Scholar
  24. 24.
    D.-J. Liaw, B.-Y. Liaw, P.-N. Hsu and C.-Y. Hwang, Chem. Mater., 13, 811 (2001).CrossRefGoogle Scholar
  25. 25.
    D.-J. Liaw, B.-Y. Liaw and C.-M. Yang, Macromolecules, 32, 7248 (1999).Google Scholar
  26. 26.
    C.-P. Yang, G.-S. Liou, R.-S. Chen and C.-Y. Yang, J. Polym. Sci., A, Polym. Chem., 38, 1090 (2000).CrossRefGoogle Scholar
  27. 27.
    F. P. Glatz and R. Mulhaupt, Polym. Bull., 31, 137 (1993).CrossRefGoogle Scholar
  28. 28.
    F. Li, S. Fang, J.-J. Ge, P. S. Honigfort, J.-C. Chen, F.-W. Harris and S. Z. D. Cheng, Polymer, 40, 4571 (1999).CrossRefGoogle Scholar
  29. 29.
    F. Li, J.-J. Ge, P.-S. Honigfort, S. Fang, J.-C. Chen, F.-W. Harris and S. Z. D. Cheng, Polymer, 40, 4987 (1999).CrossRefGoogle Scholar
  30. 30.
    K.-H. Kim, S. Jang and F.-W. Harris, Macromolecules, 34, 8925 (2001).CrossRefGoogle Scholar
  31. 31.
    J. Fang, X. Guo, S. Harada, T. Watari, K. Tanaka, H. Kita and K. I. Okamoto, Macromolecules, 35, 9022 (2002).CrossRefGoogle Scholar
  32. 32.
    T. Matsuura, S. Ando and S. Sasaki, In G. Hougham, P.-E. Gassidy, K. John and T. Davidson, (Eds.), Fluoropolymer 2: Properties, Plenum, New York, pp 305, 1999.Google Scholar
  33. 33.
    K. Han, H.-J. Lee and T.-H. Rhee, J. Appl. Polym. Sci., 74, 107 (1999).CrossRefGoogle Scholar
  34. 34.
    D.-J. Liaw, B.-Y. Liaw and M.-Q. Jeng, Polymer, 39, 1597 (1998).CrossRefGoogle Scholar
  35. 35.
    D.-J. Liaw, B.-Y. Liaw, J.-R. Chen and C.-M. Yang, Macromolecules, 32, 6860 (1999).CrossRefGoogle Scholar
  36. 36.
    C.-F. Yang, H.-D. Chen, K.-H. Yang, M.-K. Leung, C.-C. Wu, C.-C. Yang, C.-C. Wang and W.-S. Fann, Mater. Sci. Eng. B, 85, 236 (2001).CrossRefGoogle Scholar
  37. 37.
    M.-K. Leung, M.-Y. Chou, Y.-O. Su, C.-L. Chiang, H.-L. Chen, C.-F. Yang, C.-C. Yang, C.-C. Lin and H.-T. Chen, Org. Lett., 5, 839 (2003).CrossRefGoogle Scholar
  38. 38.
    G.-S. Liou, S.-H. Hsiao and Y.-K. Fang, J. Polym. Sci., A, Polym. Chem., 44, 6466 (2006).CrossRefGoogle Scholar
  39. 39.
    Y. Oishi, H. Takado, M. Yoneyama, M. Kakimoto and Y. Imai, J. Polym. Sci., A, Polym. Chem., 28, 1763 (1990).CrossRefGoogle Scholar
  40. 40.
    S.-H. Cheng, S.-H. Hsiao, T.-H. Su and G.-S. Liou, Macromolecules, 38, 307 (2005).CrossRefGoogle Scholar
  41. 41.
    G.-S. Liou, M. Maruyama, M. Kakimoto and Y. Imai, J. Polym. Sci., A, Polym. Chem., 31, 3273 (1993).CrossRefGoogle Scholar
  42. 42.
    N. Yamazaki, F. Higashi and J. Kawabata, J. Polym. Sci., Polym. Chem. Ed., 12, 2149 (1974).CrossRefGoogle Scholar
  43. 43.
    N. Yamazaki, M. Matusumoto and F. Higashi, J. Polym. Sci., Polym. Chem. Ed., 13, 1375 (1975).Google Scholar
  44. 44.
    T.-H. Su, S.-H. Hsiao and G.-S. Liou, J. Polym. Sci., A, Polym. Chem., 43, 2085 (2005).CrossRefGoogle Scholar
  45. 45.
    R. J. Mortimer and J. R. Reynolds, J. Mater. Chem., 15, 2226 (2005).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  1. 1.Functional Polymeric Materials Research Laboratory, Department of Applied ChemistryNational Chi Nan UniversityPuli, Nantou HsienRepublic of China

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