Skip to main content
SpringerLink
Log in

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

  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

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.

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14

Similar content being viewed by others

References

  1. D.-J. Liaw, F.-C. Chang, M.-K. Leung, M.-Y. Chou and K. Muellen, Macromolecules, 38, 4024 (2005).

    Article  CAS  Google Scholar 

  2. H.-S. Kim, Y.-H. Kim, S.-K. Ahn and S.-K. Kwon, Macromolecules, 36, 2327 (2003).

    Article  CAS  Google Scholar 

  3. K.-H. Kim, S. Jang and F.-W. Harris, Macromolecules, 34, 8925 (2001).

    Article  CAS  Google Scholar 

  4. S.-H. Lin, F. Li, S. Z. D. Cheng and F.-W. Harris, Macromolecules, 31, 2080 (1998).

    Article  CAS  Google Scholar 

  5. K.-C. Chuang, J.-D. Kinder, D. L. Hull, D.-B. McConville and W.-J. Youngs, Macromolecules, 30, 7183 (1997).

    Article  CAS  Google Scholar 

  6. C.-P. Yang, S.-H. Hsiao, C.-Y. Tsai and G.-S. Liou, J. Polym. Sci., A, Polym. Chem., 42, 2416 (2004).

    Article  CAS  Google Scholar 

  7. S.-H. Hsiao, C.-P. Yang, C.-Y. Tsai and G.-S. Liou, Eur. Polym. J., 40, 1081 (2004).

    Article  CAS  Google Scholar 

  8. G.-S. Liou, S.-H. Hsiao and T.-H. Su, J. Mater. Chem., 15, 1812 (2005).

    Article  CAS  Google Scholar 

  9. P.-E. Cassidy, Thermally Stable Polymers, Marcel Dekker, New York, 1980.

    Google Scholar 

  10. H.-H. Yang, Aromatic High-strength Fibers, Wiley, New York, 1989.

    Google Scholar 

  11. D.-J. Liaw and B.-Y. Liaw, Macromol. Symp., 122, 343 (1997).

    CAS  Google Scholar 

  12. C.-P. Yang, G.-S. Liou, C.-C. Yang and S.-H. Chen, J. Appl. Polym. Sci., 78, 1162 (2000).

    Article  CAS  Google Scholar 

  13. D.-J. Liaw, P.-N. Hsu, W.-H. Chen and S.-L. Lin, Macromolecules, 35, 4669 (2002).

    Article  CAS  Google Scholar 

  14. G.-S. Liou and S.-H. Hsiao, J. Polym. Sci., A, Polym. Chem., 40, 1781 (2002).

    Article  CAS  Google Scholar 

  15. G.-S. Liou, Y.-L. Yang and Y.-O. Su, J. Polym. Sci., A, Polym. Chem., 44, 2587 (2006).

    Article  CAS  Google Scholar 

  16. G.-S. Liou, H.-W. Chen and H.-J. Yen, J. Polym. Sci., A, Polym. Chem., 44, 4108 (2006).

    Article  CAS  Google Scholar 

  17. G.-S. Liou, H.-W. Chen and H.-J. Yen, Macromol. Chem. Phys., 207, 1589 (2006).

    Article  CAS  Google Scholar 

  18. M. Ballauff and G.-F. Schmidt, Macromol. Chem. Rapid. Commun., 8, 93 (1987).

    Article  CAS  Google Scholar 

  19. M. Steuer, M. Horth and M. Ballauff, J. Polym. Sci., A, Polym. Chem., 31, 1609 (1993).

    Article  CAS  Google Scholar 

  20. L. Cheng and X.-G. Jian, J. Appl. Polym. Sci., 92, 1516 (2004).

    Article  CAS  Google Scholar 

  21. G.-S. Liou, S.-H. Hsiao, W.-C. Chen and H.-J. Yen, Macromolecules, 39, 6036 (2006).

    Article  CAS  Google Scholar 

  22. G.-S. Liou and H.-J. Yen, J. Polym. Sci., A, Polym. Chem., 44, 6094 (2006).

    Article  CAS  Google Scholar 

  23. M. Yamada, T. Matsumoto and T. Kurosaki, Macromolecules, 27, 1117 (1994).

    Article  Google Scholar 

  24. D.-J. Liaw, B.-Y. Liaw, P.-N. Hsu and C.-Y. Hwang, Chem. Mater., 13, 811 (2001).

    Article  Google Scholar 

  25. D.-J. Liaw, B.-Y. Liaw and C.-M. Yang, Macromolecules, 32, 7248 (1999).

    Google Scholar 

  26. C.-P. Yang, G.-S. Liou, R.-S. Chen and C.-Y. Yang, J. Polym. Sci., A, Polym. Chem., 38, 1090 (2000).

    Article  CAS  Google Scholar 

  27. F. P. Glatz and R. Mulhaupt, Polym. Bull., 31, 137 (1993).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  30. K.-H. Kim, S. Jang and F.-W. Harris, Macromolecules, 34, 8925 (2001).

    Article  CAS  Google Scholar 

  31. J. Fang, X. Guo, S. Harada, T. Watari, K. Tanaka, H. Kita and K. I. Okamoto, Macromolecules, 35, 9022 (2002).

    Article  CAS  Google Scholar 

  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. K. Han, H.-J. Lee and T.-H. Rhee, J. Appl. Polym. Sci., 74, 107 (1999).

    Article  CAS  Google Scholar 

  34. D.-J. Liaw, B.-Y. Liaw and M.-Q. Jeng, Polymer, 39, 1597 (1998).

    Article  CAS  Google Scholar 

  35. D.-J. Liaw, B.-Y. Liaw, J.-R. Chen and C.-M. Yang, Macromolecules, 32, 6860 (1999).

    Article  CAS  Google Scholar 

  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).

    Article  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  38. G.-S. Liou, S.-H. Hsiao and Y.-K. Fang, J. Polym. Sci., A, Polym. Chem., 44, 6466 (2006).

    Article  CAS  Google Scholar 

  39. Y. Oishi, H. Takado, M. Yoneyama, M. Kakimoto and Y. Imai, J. Polym. Sci., A, Polym. Chem., 28, 1763 (1990).

    Article  CAS  Google Scholar 

  40. S.-H. Cheng, S.-H. Hsiao, T.-H. Su and G.-S. Liou, Macromolecules, 38, 307 (2005).

    Article  CAS  Google Scholar 

  41. G.-S. Liou, M. Maruyama, M. Kakimoto and Y. Imai, J. Polym. Sci., A, Polym. Chem., 31, 3273 (1993).

    Article  CAS  Google Scholar 

  42. N. Yamazaki, F. Higashi and J. Kawabata, J. Polym. Sci., Polym. Chem. Ed., 12, 2149 (1974).

    Article  CAS  Google Scholar 

  43. N. Yamazaki, M. Matusumoto and F. Higashi, J. Polym. Sci., Polym. Chem. Ed., 13, 1375 (1975).

    Google Scholar 

  44. T.-H. Su, S.-H. Hsiao and G.-S. Liou, J. Polym. Sci., A, Polym. Chem., 43, 2085 (2005).

    Article  CAS  Google Scholar 

  45. R. J. Mortimer and J. R. Reynolds, J. Mater. Chem., 15, 2226 (2005).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

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

Author information

Authors and Affiliations

  1. Functional Polymeric Materials Research Laboratory, Department of Applied Chemistry, National Chi Nan University, 1 University Road, Puli, Nantou Hsien, 54561, Taiwan, Republic of China

    Guey-Sheng Liou, Yi-Kai Fang & Hung-Ju Yen

Authors
  1. Guey-Sheng Liou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yi-Kai Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hung-Ju Yen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guey-Sheng Liou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liou, GS., Fang, YK. & Yen, HJ. Synthesis and Properties of Noncoplanar Rigid-rod Aromatic Polyamides Containing Phenyl or Naphthyl Substituents. J Polym Res 14, 147–155 (2007). https://doi.org/10.1007/s10965-006-9094-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10965-006-9094-2

Key words

Search

Navigation