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Synthesis and properties of the water-soluble self-acid-doped polypyrrole: poly[4-(3-pyrrolyl)butanesulfonic acid]

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Abstract

The water-soluble polypyrrole, poly[4-(3-pyrrolyl)butanesulfonic acid] (P3PyBSH), in which the β-position of pyrrole ring is substituted with n-butanesulfonic acid group, is synthesized by oxidation polymerization of 3PyBSNa followed with an ion-exchange of Na+ with H+. It can be cast into free-standing film from its aqueous solution and has a conductivity of 4.0×10−4 S/cm, higher than that of its sodium salt (5.5× 10−6 S/cm) by about 2 orders. The increase in conductivity is attributed to the self-doping by the protons originally on the side chains as supported by the absence of the anion FeCl4 (which generates during the polymerization) and the presence of polaron and bipolaron characteristics in its UV-Vis and IR spectra.

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References

  1. A. O. Patil, Y. Ikenoue, F. Wudl and A. J. Heeger, J. Am. Chem. Soc., 109, 1858 (1987). (b) A. O. Patil, Y. Ikenoue, N. Basescu, N. Colameri, F. Chen, F. Wudl, and A. J. Heeger, Synth. Met., 20, 151 (1987). (c) Y. Ikenoue, N. Votani, A. O. Patil, F. Wudl and A. J. Heeger, Synth. Met., 30, 305 (1989).

    CAS  Google Scholar 

  2. Y. Ikenoue, J. Chiang, A. O. Patil, F. Wudl and A. J. Heeger, J. Am. Chem. Soc., 110, 2983 (1988).

    Article  CAS  Google Scholar 

  3. Y. Ikenoue, Y. Saida, M. Kira, H. Tomozawa, H. Yashima, M. Kobayashi, and J. Chem. Soc., Chem. Commun., 1990, 1694.

  4. S.-A. Chen and M.-Y. Hua, Macromolecules, 26, 7108 (1993).

    CAS  Google Scholar 

  5. M.-Y. Hua, S.-W. Yang and S.-A. Chen, Chem. Mater., 9, 2750 (1997).

    Article  CAS  Google Scholar 

  6. N. S. Sundaresan, S. Basak, M. Pomerantz and J. R. Reynolds, J. Chem. Soc., Chem. Commun., 621 (1987).

  7. J. R. Reynolds, N. S. Sundaresan, M. Pomerantz, S. Basak and C. K. Bakes, J. Electroanal. Chem., 250, 355 (1988).

    Article  CAS  Google Scholar 

  8. E. E. Havinga, W. ten Hoeve, E. W. Meijer and H. Wynberg, Chem. Mater., 1, 650 (1989).

    Article  CAS  Google Scholar 

  9. P. J. Armes, Synth. Met., 20, 365 (1987).

    CAS  Google Scholar 

  10. R. L. Elsenbaumer and L. W. Shacklette, Handbook of Conducting Polymer, Ed. by T. A. Skothein, Marcel Dakker Inc., New York, 1986, Vol. I, p. 224.

    Google Scholar 

  11. H. E. Schaffer and A. J. Heeger, Solid State Commun., 59, 415 (1986).

    Article  CAS  Google Scholar 

  12. Z. W. Sun and A. J. Frank, J. Chem. Phys., 94, 4600 (1991).

    CAS  Google Scholar 

  13. T. Tang, X. Jing, B. Wang and F. Wang, Synth. Met., 24, 231 (1988).

    CAS  Google Scholar 

  14. B. Tian and G. Zerbi, J. Chem. Phys., 92, 3892 (1990).

    CAS  Google Scholar 

  15. J. Lei, W. Liang and C. R. Martin, Synth. Met., 48, 301 (1992).

    CAS  Google Scholar 

  16. K. Yakushi, L. J. Lanchlan, T. C. Clarke and G. B. Street, J. Chem. Phys., 79, 4774 (1983).

    Article  CAS  Google Scholar 

  17. J. C. Scott, J. L. Bredas, K. Yakushi, P. Pfluger and G. B. Street, Synth. Met., 9, 165 (1984).

    CAS  Google Scholar 

  18. E. T. Kang, K. G. Neoh and K. L. Tan, Surface and Interface Analysis, 19, 33 (1992).

    Article  CAS  Google Scholar 

  19. A. J. Epstein, J. M. Ginder, F. Zuo, R. W. Bigelow, H.-S. Woo, D. B. Tanner, A. F. Richter, W.-S. Huang and A. G. MacDiarmid, Synth. Met., 18, 303 (1987).

    CAS  Google Scholar 

  20. Y. Furukawa, F. Ueda, Y. Hyodo, I. Harada, T. Nakajima and T. Kawagoe, Macromolecules, 21, 1297 (1988).

    Article  CAS  Google Scholar 

  21. S.-A. Chen and G.-W. Hwang, Macromolecules, 29, 3950 (1996).

    CAS  Google Scholar 

  22. S.-A. Chen and G.-W. Hwang, J. Am. Chem. Soc., 116, 7939 (1994).

    CAS  Google Scholar 

  23. S.-A. Chen and G.-W. Hwang, J. Am. Chem. Soc., 117, 10055 (1995).

    Google Scholar 

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Chang, EC., Hua, MY. & Chen, SA. Synthesis and properties of the water-soluble self-acid-doped polypyrrole: poly[4-(3-pyrrolyl)butanesulfonic acid]. J Polym Res 5, 249–254 (1998). https://doi.org/10.1007/s10965-006-0064-5

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  • DOI: https://doi.org/10.1007/s10965-006-0064-5

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