Advertisement

Research on Chemical Intermediates

, Volume 44, Issue 5, pp 3375–3388 | Cite as

Synthesis and electrochemical studies of new styrenic poly(ionic liquid)s based on the 1-methyl-1,2,3-benzotriazolium cation

  • Fatemeh Soghra Jahed
  • Mohammad Galehassadi
Article
  • 146 Downloads

Abstract

The styrenic ionic liquid-based poly ionic liquids (PILs) with the advantage of facile synthesis and the ability to incorporate many desirable functional moieties offer an efficient route to highly functional styrenic PILs. On the other hand, triazole is a desirable and useful heterocyclic compound that can be used in various fields of polymer and material science to attain better properties. In this paper, a set of new styrenic ionic liquid monomers based on 1-methyl-1,2,3-benzotriazolium cation were successfully synthesized by a quaternization of 1-methyl-1,2,3-benzotriazole with 4-vinylbenzylchroride. Subsequently, an anion exchange reaction was carried out. Afterward, these styrenic ionic liquid monomers readily polymerized via free radical polymerization. The chemical structures of these monomers and polymers were confirmed by Fourier transform infrared spectroscopy and proton and carbon nuclear magnetic resonance (1H- and 13C-NMR). Furthermore, the solubility of the homopolymers in different solvents was tested. The thermal behavior of the polymers was evaluated by thermogravimetric analysis and differential scanning calorimetry. The cyclic voltammetery measurements revealed that these polymers have a larger electrochemical window compared with polystyrene.

Keywords

1-methylbenzotriazole Ionic liquid monomers Polystyrene Thermal behavior Solubility Electrochemical stability 

Notes

Acknowledgement

The authors appreciate Dr. Rahim Mohammad-Rezaei for the cyclic voltammetry studies.

Supplementary material

11164_2018_3313_MOESM1_ESM.docx (361 kb)
Supplementary material 1 (DOCX 360 kb)

References

  1. 1.
    T. Erdmenger, C. Guerrero-Sanchez, J. Vitz, R. Hoogenboom, U.S. Schubert, Chem. Soc. Rev. 39, 3317 (2010)CrossRefGoogle Scholar
  2. 2.
    J. Lu, F. Yan, J. Texter, Prog. Polym. Sci. 34, 431 (2009)CrossRefGoogle Scholar
  3. 3.
    M. Xiao, Free Radical Polymerization in Room Temperature Ionic Liquids. Master’s thesis, University of Tennessee, (2006)Google Scholar
  4. 4.
    H. Zhang, K. Hong, J.W. Mays, Macromolecules 35, 5738 (2002)CrossRefGoogle Scholar
  5. 5.
    J. Yuan, D. Mecerreyes, M. Antonietti, Prog. Polym. Sci. 38, 1009 (2013)CrossRefGoogle Scholar
  6. 6.
    Y. Men, D. Kuzmicz, J. Yuan, Curr. Opin. Colloid Interface Sci. 19, 76 (2014)CrossRefGoogle Scholar
  7. 7.
    J. Yuan, M. Antonietti, Polymer 52, 1469 (2011)CrossRefGoogle Scholar
  8. 8.
    P. Dimitrov-Raytchev, S. Beghdadi, A. Serghei, E. Drockenmuller, J. Polym. Sci., Part A: Polym. Chem. 51, 34 (2013)CrossRefGoogle Scholar
  9. 9.
    J. Mythri, B.S. Anusha, M. Srinivasa Reddy, J. Chem. Pharm. Sci (2014) ISSN: 0974-2115Google Scholar
  10. 10.
    R. Sood, M.M. Obadia, B.P. Mudraboyina, B. Zhang, A. Serghei, J. Bernard, E. Drockenmuller, Polym. 55, 3314 (2014)CrossRefGoogle Scholar
  11. 11.
    P. Wang, Y.-N. Zhou, J.-S. Luo, Z.-H. Luo, Polym. Chem. 5, 882 (2014)CrossRefGoogle Scholar
  12. 12.
    B.J. Adzima, S.C. Taylor, H. He, D.R. Luebke, K. Matyjaszewski, H.B. Nulwala, J. Polym. Sci., Part A: Polym. Chem. 52, 417 (2014)CrossRefGoogle Scholar
  13. 13.
    J. Yang, J. Zheng, J. Zhang, L. Sun, F. Chen, P. Fan, M. Zhong, RSC Adv. 5, 32853 (2015)CrossRefGoogle Scholar
  14. 14.
    E.B. Anderson, T.E. Long, Polymer 51, 2447 (2012)CrossRefGoogle Scholar
  15. 15.
    C. Detrembleur, A. Debuigne, M. Hurtgen, C. Jerome, Macromolecules 44, 6397 (2011)CrossRefGoogle Scholar
  16. 16.
    D. Mecerreyes, Prog. Polym. Sci. 36, 1629 (2011)CrossRefGoogle Scholar
  17. 17.
    S. Koguchi, K. Izawa, ACS combinatorial science. 16, 381 (2014)CrossRefGoogle Scholar
  18. 18.
    S.A. Forsyth, D.R. MacFarlane, J. Mater. Chem. 13, 2451 (2003)CrossRefGoogle Scholar
  19. 19.
    A. Mudzakir, Indonesian J. Chem. 6, 111 (2006)Google Scholar
  20. 20.
    N.H. Buttrus, A.A. Sabah, A.A. Taqa, U. Englert, Acta Cryst. 68, 02735 (2012)Google Scholar
  21. 21.
    S. Sanghi, E. Willett, C. Versek, M. Tuominen, E.B. Coughlin, RSC Adv. 2, 848 (2012)CrossRefGoogle Scholar
  22. 22.
    W. Zhang, J. Yuan, Macromol. Rapid Commuin. 37, 1124 (2016)CrossRefGoogle Scholar
  23. 23.
    B.P. Mudraboyina, M.M. Obadia, I. Allaoua, R. Sood, A. Serghei, E. Drockenmuller, Chem. Mater. 26, 1720 (2014)CrossRefGoogle Scholar
  24. 24.
    S. Zhang, Y. Hou, W. Huang, Y. Shan, Electrochim. Acta 50, 4097 (2005)CrossRefGoogle Scholar
  25. 25.
    W. Yuan, H. Jin, J.-K. Chung, J. Zheng, Chem. Biol. Interact. 186, 323 (2010)CrossRefGoogle Scholar
  26. 26.
    B.A. Howell, K. Chaiwong, J. Therm. Anal. Calorim. 96, 219 (2009)CrossRefGoogle Scholar
  27. 27.
    M. Assadi, F. Hosseinzadeh, Des. Monomers Polym. 13, 181 (2010)CrossRefGoogle Scholar
  28. 28.
    J.E. Bara, E.S. Hatakeyama, D.L. Gin, R.D. Noble, Polym. Adv. Technol. 19, 1415 (2008)CrossRefGoogle Scholar
  29. 29.
    J. Tang, H. Tang, W. Sun, M. Radosz, Y. Shen, Polym. 46, 12460 (2005)CrossRefGoogle Scholar
  30. 30.
    H. Tang, J. Tang, S. Ding, M. Radosz, Y. Shen, J. Polym. Sci. Part A: Polm. Chem. 43, 1432 (2005)CrossRefGoogle Scholar
  31. 31.
    J. Steinkoenig, F.R. Bloesser, B. Huber, A. Welle, V. Trouillet, S.M. Weidner, L. Barner, P.W. Roesky, J. Yuan, A.S. Goldmann, C. Barner-Kowollik, Polym. Chem. 7, 451 (2016)CrossRefGoogle Scholar
  32. 32.
    J. Tang, Y. Shen, M. Radosz, W. Sun, Ind. Eng. Chem. Res. 48, 9113 (2009)CrossRefGoogle Scholar
  33. 33.
    A.R. Katritzky, W. Kuzmierkiewicz, J.V. Greenhill, Recl. Trav. Chim. Pays-Bas 110, 369 (1991)CrossRefGoogle Scholar
  34. 34.
    F. Hosseinzadeh, M. Mahkam, M. Galehassadi, Des. Monomers Polym. 15, 379 (2012)CrossRefGoogle Scholar
  35. 35.
    M. Galehassadi, R. Herizchi, F. Ranjbar, Des. Monomers Polym. 14, 303 (2011)CrossRefGoogle Scholar
  36. 36.
    B.K.M. Chan, N.-H. Chang, M.R. Grimmett, Aust. J. Chem. 30, 2005 (1977)CrossRefGoogle Scholar
  37. 37.
    R.K. Donato, M.V. Migliorini, M.A. Benvegnú, J. Dupont, R.S. Gonçalves, H.S. Schrekker, J. Solid State Electtrochem. 11, 1481 (2007)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceAzarbaijan Shahid Madani UniversityTabrizIran

Personalised recommendations