Facile Synthesis and Characterization of Poly(dialkoxy-p-phenylene 1,3,4-oxadiazole-alt-phenylene 1,3,4-oxadiazole)s

  • Published : 2008.06.30

Abstract

Poly(dialkoxyphenylene 1,3,4-oxadiazole)s were conveniently synthesized to compare their material properties of solvent solubility, thermal stability and molecular alignment with respect to alkyl chain length and meta/para-phenylene structure. All prepared polymers exhibited good solubility in co-solvents containing various volume levels of chloroform to trifluoroacetic acid. Meta-polymers showed slightly better solubility than para-polymers. All polymers produced were thermally stable up to $320^{\circ}C$. Photoluminescence of polymer films was observed with blue light emission at around 450 nm. X-ray diffraction patterns of all polymers indicated that they were composed of stacked molecular sheets with the same layer-to-layer distance of $3.4\;{\AA}$. However, side chain-to-side chain and main chain-to-main distances within the layers increased with increasing alkyl chain lengths. The meta-polymer chains were separated more than the para-polymer chains.

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References

  1. C. K. Chiang, C. R. Fisnher, Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis, S. C. Gau, and A. G. MacDiarmid, Phys. Rev. Lett., 39, 1089 (1977)
  2. R. M. Tarkka, X. Zhang, and S. A. Jeneckhe, J. Am. Chem. Soc., 118, 9438 (1996)
  3. Y. H. Kim, S. J. Park, J. W. Park, J. H. Kim, and S. K. Kim, Macromol. Res., 15, 216 (2007) https://doi.org/10.1007/BF03218778
  4. G. Lu, J. Gao, J. C. Hummelen, F. Wudl, and A. J. Heeger, Science, 270, 1789 (1995) https://doi.org/10.1126/science.270.5243.1789
  5. M. Granstrom, K. Petritsch, A. C. Arias, A. Lux, M. R. Andersson, and R. H. Friend, Nature, 395, 257 (1998) https://doi.org/10.1038/26183
  6. Y. Yang and A. J. Heeger, Nature, 372, 344 (1994) https://doi.org/10.1038/372344a0
  7. A. H. Frazer and I. M. Sarasohn, J. Polym. Sci. Polym. Chem., 4, 1649 (1966) https://doi.org/10.1002/pol.1966.150040701
  8. M. Ueda and M. Oda, Polym. J., 21, 193 (1989) https://doi.org/10.1295/polymj.21.193
  9. C. Kummerloewe, H. W. Kammer, M. Malincomico, and E. Martusceli, Polymer, 32, 2505 (1991) https://doi.org/10.1016/0032-3861(91)90328-G
  10. M. A. De-Paolai, R. J. Waltman, A. F. Diaz, and J. Bargon, J. Polym. Sci. Polym. Chem. Ed., 23, 1687 (1985) https://doi.org/10.1002/pol.1985.170230610
  11. J. H. Edward, W. J. Feast, and D. C. Bott, Polymer, 25, 395 (1984) https://doi.org/10.1016/0032-3861(84)90293-3
  12. G. Maglio, R. Palumbo, M. Tortora, M. Trifuoggi, and G. Varricchio, Polymer, 39, 6407 (1998) https://doi.org/10.1016/S0032-3861(97)10383-4
  13. W. Huang, W. L. Yu, H. Meng, J. Pei, and S. F. Y. Li, Chem. Mater., 10, 3340 (1998) https://doi.org/10.1021/cm9800581
  14. R. Stern, M. Ballauff, G. Lieser, and G. Wegner, Polymer, 11, 2096 (1991)
  15. U. Caruso, S. Pragliola, A. Roviello, A. Sirigu, and P. Iannelli, Macromolecules, 28, 6089 (1995) https://doi.org/10.1021/ma00122a014
  16. Z. Bao, Y. Chen, R. Cai, and L. Yu, Macromolecules, 26, 5281 (1993) https://doi.org/10.1021/ma00072a002
  17. B. R. Harkness and J. Watanabe, Macromolecules, 24, 6759 (1991) https://doi.org/10.1021/ma00025a031
  18. D. Capitani, P. Laurienzo, M. Malinconico, N. Proietti, and A. Roviello, J. Polym. Sci. Polym. Chem., 41, 3916 (2003) https://doi.org/10.1002/pola.10935
  19. M. Gillo, P. Iannelli, P. Laurienzo, M. Malinconico, A. Roviello, P. Mormile, and L. Petti, Chem. Mater., 14, 1539 (2002) https://doi.org/10.1021/cm011134u
  20. J. Keum, C. S. Ha, and Y. Kim, Macromol. Res., 14, 401 (2006) https://doi.org/10.1007/BF03219101
  21. P. E. Cassidy, Thermally Stable Polymers, Marcel Dekker, New York, 1980, p 67