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Alkylated sulfonated poly(arylene sulfone)s for proton exchange membranes

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Abstract

The attachment of flexible spacers into aromatic polymers is a molecular design approach that is used for improving processability of aromatic polymers. The concept is attractive because it enables not only the creation of aromatic polymers with improved processability but it is also possible to control phase morphology by simply introducing pendant side chains. Here we report new bisphenol A derivatives bearing alkyl chains of different lengths obtained by an addition reaction can readily make novel poly(arylene sulfone)s with aromatic dihalides and aromatic dioles. They were observed using two-dimension diffusion-ordered spectroscopy nuclear magnetic resonance (2D DOSY NMR) spectra. Attaching flexible alkyl groups into sulfonated poly(arylene sulfone)s allows for increased control of glass transition temperatures, T g , of sulfonated poly(arylene sulfone)s. The alkylated sulfonated poly(arylene sulfone)s had flexibility, increased surface contact angle, improved methanol permeability, and high ion conductivity compared to the neat polymer. Due to the creation of aromatic polymers with improved processability by simply introducing pedant side chains, this novel alkylation method is expected to be applicable to other arylene based proton conductive polymers.

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References

  1. B. C. H. Steele and A. Heinzel, Nature, 414, 345 (2001).

    Article  CAS  Google Scholar 

  2. M. Rikukawa and K. Sanui, Prog. Polym. Sci., 25, 1463 (2000).

    Article  CAS  Google Scholar 

  3. K. D. Kreuer, J. Membr. Sci., 185, 29 (2001).

    Article  CAS  Google Scholar 

  4. M. A. Hickner, H. Ghassemi, Y. S. Kim, B. R. Einsla, and J. E. McGrath, Chem. Rev., 104, 4587 (2004).

    Article  CAS  Google Scholar 

  5. G. Alberti and M. Casciola, Annu. Rev. Mater. Res., 33, 129 (2003).

    Article  CAS  Google Scholar 

  6. A. S. Arico, P. Bruce, B. Scrosati, J.-M. Tarascon, and W. van Schalkwijk, Nat. Mater., 4, 366 (2005).

    Article  CAS  Google Scholar 

  7. R. Borup, J. Meyers, B. Pivovar, Y. S. Kim, R. Mukundan, N. Garland, D. Myers, M. Wilson, F. Garzon, D. Wood, P. Zelenay, K. More, K. Stroh, T. Zawodzinski, J. Boncella, J. E. McGrath, M. Inaba, K. Miyatake, M. Hori, K. Ota, Z. Ogumi, S. Miyata, A. Nishikata, Z. Siroma, Y. Uchimoto, K. Yasuda, K.-I. Kimijima, and N. Iwashita, Chem. Rev., 107, 3904 (2007).

    Article  CAS  Google Scholar 

  8. W. L. Harrison, F. Wang, J. B. Mecham, V. A. Bhanu, M. Hill, Y. S. Kim, and J. E. McGrath, J. Polym. Sci., Part A: Polym. Chem., 41, 2264 (2003).

    Article  CAS  Google Scholar 

  9. F. Wang, M. Hickner, Y. S. Kim, T. A. Zawodzinski, and J. E. McGrath, J. Membr. Sci., 197, 231 (2002).

    Article  CAS  Google Scholar 

  10. W. L. Harrison, M. A. Hickner, Y. S. Kim, and J. E. McGrath, Fuel Cells, 5, 201 (2005).

    Article  CAS  Google Scholar 

  11. S. Elamathi, G. Nithyakalyani, D. Sangeetha, and S. Ravichandran, Ionics, 14, 377 (2008).

    Article  CAS  Google Scholar 

  12. J. Pang, H. Zhang, X. Li, and Z. Jiang, Macromolecules, 40, 9435 (2007).

    Article  CAS  Google Scholar 

  13. Y. S. Kim, L. Dong, M. A. Hickner, B. S. Pivovar, and J. E. McGrath, Polymer, 44, 5729 (2003).

    Article  CAS  Google Scholar 

  14. Y. S. Kim, B. Einsla, M. Sankir, W. Harrison, and B. S. Pivovar, Polymer, 47, 4026 (2006).

    Article  CAS  Google Scholar 

  15. I. H. Sung, D. M. Yu, Y. J. Yoon, T.-H. Kim, J. Y. Lee, S. K. Hong, and Y. T. Hong, Macromol. Res., 21, 1138 (2013).

    Article  CAS  Google Scholar 

  16. H. K. Kim, D. H. Kim, J. Choi, and S. C. Kim, Macromol. Res., 19, 928 (2011).

    Article  CAS  Google Scholar 

  17. D. J. Kim, S. M. Woo, and S. Y. Nam, Macromol. Res., 20, 1075 (2012).

    Article  CAS  Google Scholar 

  18. J. Miyake, T. Mochizuki, and K. Miyatake, ACS Macro Lett., 4, 750 (2015).

    Article  CAS  Google Scholar 

  19. B. Lafitte and P. Jannasch, Adv. Funct. Mater., 17, 2823 (2007).

    Article  CAS  Google Scholar 

  20. E. P. Jutemar and P. Jannasch, J. Membr. Sci., 351, 87 (2010).

    Article  CAS  Google Scholar 

  21. J. Parvole and P. Jannasch, J. Mater. Chem., 18, 5547 (2008).

    Article  CAS  Google Scholar 

  22. P. Jannasch, Fuel Cells, 5, 248 (2005).

    Article  CAS  Google Scholar 

  23. S. N. Huckin and L. Weiler, J. Am. Chem. Soc., 96, 1082 (1974).

    Article  CAS  Google Scholar 

  24. H.-S. Dang, E. A. Weiber, and P. Jannasch, J. Mater. Chem. A, 3, 5280 (2015).

    Article  CAS  Google Scholar 

  25. E. W. Dezmelyk and R. S. Reed, Ind. Eng. Chem., 53, 68A (1961).

    Article  Google Scholar 

  26. R. A. Finnegan and H. W. Kutta, J. Org. Chem., 30, 4138 (1965).

    Article  CAS  Google Scholar 

  27. J. Wang, S. Li, and S. Zhang, Macromolecules, 43, 3890 (2010).

    Article  CAS  Google Scholar 

  28. T. Ko, K. Kim, B.-K. Jung, S.-H. Cha, S.-K. Kim, and J.-C. Lee, Macromolecules, 48, 1104 (2015).

    Article  CAS  Google Scholar 

  29. M. Kumar and M. Ulbricht, RSC Adv., 3, 12190 (2013).

    Article  CAS  Google Scholar 

  30. F. Zhang, H. Zhang, and C. Qu, J. Mater. Chem., 21, 12744 (2011).

    Article  CAS  Google Scholar 

  31. A. H. N. Rao, S. Nam, and T.-H. Kim, J. Mater. Chem. A, 3, 8571 (2015).

    Article  CAS  Google Scholar 

  32. D. Guo, A. N. Lai, C. X. Lin, Q. G. Zhang, A. M. Zhu, and Q. L. Liu, ACS Appl. Mater. Interfaces, 8, 25279 (2016).

    Article  CAS  Google Scholar 

  33. C. Gouri, C. P. Reghunadhan Nair, and R. Ramaswamy, Polym. Int., 50, 403 (2001).

    Article  CAS  Google Scholar 

  34. P. J. Flory, J. Am. Chem. Soc., 59, 241 (1937).

    Article  CAS  Google Scholar 

  35. M. Yoshioka and T. Otsu, Macromolecules, 25, 2599 (1992).

    Article  CAS  Google Scholar 

  36. Y. S. Choi, T. K. Kim, E. A. Kim, S. H. Joo, C. Pak, Y. H. Lee, H. Chang, and D. Seung, Adv. Mater., 20, 2341 (2008).

    Article  CAS  Google Scholar 

  37. S. H. Joo, C. Pak, E. A. Kim, Y. H. Lee, H. Chang, D. Seung, Y. S. Choi, J.-B. Park, and T. K. Kim, J. Power Sources, 180, 63 (2008).

    Article  CAS  Google Scholar 

  38. Y. S. Kim, F. Wang, M. Hickner, S. McCartney, Y. T. Hong, W. Harrison, T. A. Zawodzinski, and J. E. McGrath, J. Polym. Sci., Part B: Polym. Phys., 41, 2816 (2003).

    Article  CAS  Google Scholar 

  39. G. J. M. Janssen, E. F. Sitters, and A. Pfrang, J. Power Sources, 191, 501 (2009).

    Article  CAS  Google Scholar 

  40. N. Ramaswamy, N. Hakim, and S. Mukerjee, Electrochim. Acta, 53, 3279 (2008).

    Article  CAS  Google Scholar 

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Correspondence to Yeong Suk Choi.

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Acknowledgments: This work was supported by Samsung Advanced Institute of Technology.

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Lee, W.J., Lee, S.H., Bayazit, M.K. et al. Alkylated sulfonated poly(arylene sulfone)s for proton exchange membranes. Macromol. Res. 25, 400–407 (2017). https://doi.org/10.1007/s13233-017-5057-1

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  • DOI: https://doi.org/10.1007/s13233-017-5057-1

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