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The oxidative polycondensation of 2-[(4-pyridilmethylene)-imino]phenol by molecular O2 in alkaline medium: Synthesis and characterization

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Summary

The polymer of 2-[(4-pyridilmethylene)-imino] phenol (2-PIP) has been formed from the oxidative polycondensation (OP) reaction by using molecular O2 as the oxidant in an aqueous alkaline medium between 60–90 °C. The optimum reaction conditions and the main parameters of the process were determined. The yield of polymer was found as 50.1%. The structures of synthesized monomer and polymer were confirmed by FT-IR, UV-vis, 1H-13C-NMR and elemental analysis. The characterization was made by TGA-DTA, size exclusion chromatography (SEC) and solubility tests. The 1H-13C-NMR data shows that the polymerization proceeded with C-C and C-O-C coupling system of ortho and para positions and oxyphenylene according to –OH group of 2-PIP. The molecular weight distribution values of the product were determined from SEC measurement. The number-average molecular weight (Mn), weight-average molecular weight (Mw) and polydispersity index (PDI) values of poly-2-[(4-pyridilmethylene)-imino]phenol (poly-2-PIP) were found to be 11350, 12600 g.mol-1 and 1.110, respectively. According to thermo gravimetric analysis (TGA), the carbon residues of 2-PIP and poly-2-PIP were found to be 18.17% and 45.10%, respectively, at 1000 °C.

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References

  1. Saegusa, Y., Sekiba, K., Nakamura, S. (1990) J. Polym. Sci. Part A: Polym. Chem. 28 (13), 3647.

    Google Scholar 

  2. Cerrada, P., Oriol, L., Pinol, M., Serrano, JL. (1997) J. Am. Chem. Soc. 119 (32), 7581.

    Google Scholar 

  3. Fujiwara, M., Mori, W., Yamaguti, K. (1995) Mol. Cryst. Liq. Cryst. 247, 175.

  4. Cerrada, P., Oriol, L., Pinol, M., Serrano, J. S. (1996) J. Polym. Sci. Part A Polym. Chem. 34 (13), 2603.

    Google Scholar 

  5. Jenekhe, S.A., Yang, C. J., Vanherzeele, H., Meth, S. (1991) Chem. Mater. 3 (6), 985.

    Google Scholar 

  6. Choi, E.J., Ahn, J.C., Chien, L.C., Lee, C.K., Zin, W.C., Kim, D.C., Shin, S.T. (2004) Macromolecules, 37 (1), 71.

  7. Lee, K. S., Won, J. C., Jung, J. C. (1989) Macromol. Chem., 190 (7), 1547.

    Google Scholar 

  8. Park, S. B., Kim, H., Zin, W. C., Jung, J. C. (1993) Macromolecules, 26 (7), 1627.

  9. Wang, C., Shieh, S., LeGoff, E., Kanatzidis, M. G. (1996) Macromolecules, 29 (9), 3147.

  10. Misra, M., Das, D., Padhi, K. B., Panigrahi, A. K., Mohanty, A. K. (1998) J. Macromol. Sci. Pure Appl. Chem., A35 (5), 867.

  11. Park, K. H., Tani, T., Kakimoto, M., Imai, Y. (1998) Macromol. Chem. Phys., 199 (6), 1029.

    Google Scholar 

  12. El-Shekeil AG, Al-Yusufy FA and Saknidy S, (1997) Polymer International, 42: 39.

  13. Suh SC and Shim SC, (2000) Synthetic Metals, 114 (1), 91.

  14. Niu HJ, Huang Yu-D, Bai Xu-D and Li X, (2004) Materials Letters, 58, 2979.

  15. Yang CJ and Jenekhe SA, (1995) Macromolecules, 28, 1180.

  16. Ragimov AV, Mamedov BA and Gasanova SG, (1997), Polymer International, 43 (4), 343.

    Google Scholar 

  17. Baughman RH, Bredas JL, Chance RR, Elsenbaumer RL and Shacklette LW, (1982), Chem. Rev., 82, 209.

    Google Scholar 

  18. Diaz FR, Moreno J, Tagle LH, East GA and Radic D, (1999), Synthetic Metals, 100 (2), 187.

  19. Aly KI and Khalaf AA, (2000) J. Appl. Polym. Sci., 77 (6), 1218.

  20. Kaya İ, Vilayetoğlu AR and Topak H, (2002) J Appl. Polym. Sci., 85 (9), 2004.

  21. Kaya İ, Demir HÖ and Vilayetoğlu AR, (2002), Synthetic Metals, 126 (2, 3), 183.

  22. Kaya İ and Bilici A, (2006), J Macromolecular Science Part A: Pure and Applied Chemistry, 43 (4-5) 719.

    Google Scholar 

  23. Ayyagari, M. S., Marx, K. A., Tripathy, S. K., Akkara, J. A. and Kaplan, D. L., (1995) Macromolecules, 28, 5192.

  24. Kaya İ. and Bilici A. (2006) Synthetic Metals, 156 (9-10) 736.

  25. Kaya İ., Karayiğitler H. and Özdemir E., (2006) International Journal of Polymer Analysis and Characterization, 11 (4), 271.

    Google Scholar 

  26. Cazacu, M., Marcu, M., Vlad, A., Rusu, G.I., and Avadanei, M. (2004) Journal of Organometallic Chemistry, 689, 3005.

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Science, Department of Chemistry, Ankara University, Ankara, Turkey

    H.Ökkeş Demir & Mehmet Saçak

  2. Faculty of Science & Art, Department of Chemistry, Çanakkale Onsekiz Mart University, 17020, Çanakkale, Turkey

    İsmet Kaya

Authors
  1. H.Ökkeş Demir
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  2. İsmet Kaya
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  3. Mehmet Saçak
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Correspondence to İsmet Kaya.

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Demir, H., Kaya, İ. & Saçak, M. The oxidative polycondensation of 2-[(4-pyridilmethylene)-imino]phenol by molecular O2 in alkaline medium: Synthesis and characterization. Polym. Bull. 60, 37–48 (2008). https://doi.org/10.1007/s00289-007-0836-z

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  • DOI: https://doi.org/10.1007/s00289-007-0836-z

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