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Poly tris (1-imidazolyl) benzene ionic liquids/Poly (2,6-dimethyl phenylene oxide) composite membranes for anion exchange membrane fuel cells

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Abstract

To improve the conductivity of anion exchange membranes without reducing the mechanical properties, a series of poly ionic liquids (PILs) with precursors of 1,3,5-tris(1-imidazolyl)benzene (TIB) containing tri-conduct groups were synthesized and incorporated into quaternized poly (2,6-dimethyl phenylene oxide) (QPPO) membranes. The new poly ionic liquids we designed contain ternary conduct groups in one monomer which are advantageous to form ionic channels and thus dramatically increase the conductivity of membranes. Various alkyl chains were introduced into TIB during polymerization to tune the distance between two tri-conduct groups. The resulting PILs/QPPO composite membranes showed good thermal stability, appropriate mechanical properties, enhanced conductivity and fuel cell performance. When the numbers of –CH2– between two tri-conduct groups reached 12, the composite membrane showed the highest conductivity and fuel cell performance (55.5 mS/cm at 80 °C and 168.9 mW/cm2). The composite membranes we prepared show potential application in anion exchange membrane fuel cells (AEMFCs).

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References

  1. Wang J, Wang L (2014) Preparation and properties of organic–inorganic alkaline hybrid membranes for direct methanol fuel cell application. Solid State Ion 255:96–103

    Article  Google Scholar 

  2. Hu Y, Gu D, Li F, Qi X, Yang K, Liu X, Li H, Zhang Y (2016) Synthesis of fluorinated block copolymer electrolyte containing quaternary ammonium base. J Mater Sci 51:5834–5842. doi:10.1007/s10853-016-9884-9

    Article  Google Scholar 

  3. Hu J, Zhang CX, Zhang XD, Chen LW, Jiang L, Meng YD, Wang XK (2014) A green approach for preparing anion exchange membrane based on cardo polyetherketone powders. J Power Sources 272:211–217

    Article  Google Scholar 

  4. Wu L, Pan Q, Varcoe JR, Zhou D, Ran J, Yang ZJ, Xu TW (2015) Thermal crosslinking of an alkaline anion exchange membrane bearing unsaturated side chains. J Membr Sci 490:1–8

    Article  Google Scholar 

  5. Venkatesan PN, Dharmalingam S (2015) Development of cation exchange resin-polymer electrolyte membranes for microbial fuel cell application. J Mater Sci 50:6302–6312. doi:10.1007/s10853-015-9167-x

    Article  Google Scholar 

  6. Xiong Y, Liu QL, Zeng QH (2009) Quaternized cardo polyetherketone anion exchange membrane for direct methanol alkaline fuel cells. J Power Sources 193:541–546

    Article  Google Scholar 

  7. Fang J, Shen PK (2006) Quaternized poly (phthalazinon ether sulfone ketone) membrane for anion exchange membrane fuel cells. J Membr Sci 285:317–322

    Article  Google Scholar 

  8. Rao A, Kim H, Nam S, Kim T (2013) Cardo poly (arylene ether sulfone) block copolymers with pendant imidazolium side chains as novel anion exchange membranes for direct methanol alkaline fuel. Polymer 54:6918–6928

    Article  Google Scholar 

  9. Pérez-Prior MT, García-García T, Várez A, Levenfeld B (2015) Preparation and characterization of ammonium-functionalized polysulfone/Al2O3 composite membranes. J Mater Sci 50:5893–5903. doi:10.1007/s10853-015-9139-1

    Article  Google Scholar 

  10. Li Q, Liu L, Liang S, Dong Q, Jin B, Bai R (2013) Preparation and characterization of composite membranes with ionic liquid polymer-functionalized multiwalled carbon nanotubes for alkaline fuel cells. RSC Adv 3:13477–13485

    Article  Google Scholar 

  11. Park AM, Wycisk RJ, Ren Xiaoming, Turley FE, Pintauro PN (2015) Crosslinked poly(phenylene oxide)-based nanofiber composite membranes for alkaline fuel cells. J Mater Chem A 4:132–141

    Article  Google Scholar 

  12. Wu H, Jia W, Liu Y (2017) An imidazolium-type hybrid alkaline anion exchange membrane with improved membrane stability for alkaline fuel cells applications. J Mater Sci 52:1704–1716. doi:10.1007/s10853-016-0462-y

    Article  Google Scholar 

  13. Zhu L, Pan J, Wang Y, Han J, Zhuang L, Hickner MA (2016) Multication side chain anion exchange membranes. Macromolecules 49:815–824

    Article  Google Scholar 

  14. Wu L, Zhou G, Liu X, Zhang ZH, Li C, Xu T (2011) Environmentally friendly synthesis of alkaline anion exchange membrane for fuel cells via a solvent-free strategy. J Membr Sci 371:155–162

    Article  Google Scholar 

  15. Zarrin H, Wu J, Fowler M, Chen Z (2012) High durable PEK-based anion exchange membrane for elevated temperature alkaline fuel cells. J Membr Sci 394:193–201

    Article  Google Scholar 

  16. Zhang Y, Li C, Yang Z, Liu X, Dong J, Liu Y, Cai W, Cheng H (2017) A robust pendant-type cross-linked anion exchange membrane (AEM) with high hydroxide conductivity at a moderate IEC value. J Mater Sci 52:3946–3958. doi:10.1007/s10853-016-0656-3

    Article  Google Scholar 

  17. Gu S, Cai R, Luo T, Chen Z, Sun M, Liu Y, He G, Yan Y (2009) A soluble and highly conductive ionomer for high-performance hydroxide exchange membrane fuel cells. Angew Chem Int Ed 48:6499–6502

    Article  Google Scholar 

  18. Guo M, Fang J, Xu H, Li W, Lu X, Lan C, Li K (2010) Synthesis and characterization of novel anion exchange membranes based on imidazolium-type ionic liquid for alkaline fuel cells. J Membr Sci 362:97–104

    Article  Google Scholar 

  19. Wang J, Li S, Zhang S (2010) Novel hydroxide-conducting polyelectrolyte composed of an poly(arylene ether sulfone) containing pendant quaternary guanidinium groups for alkaline fuel cell applications. Macromolecules 43:3890–3896

    Article  Google Scholar 

  20. Chu Y, Chen Y, Chen N, Wang F, Zhu H (2016) A new method for improving the ion conductivity of anion exchange membranes by using TiO2 nanoparticles coated with ionic liquid. RSC Adv 6:96768–96777

    Article  Google Scholar 

  21. Wang C, Lin B, Qiao G, Wang L, Zhu L, Chu F, Feng T, Yuan N, Ding J (2016) Polybenzimidazole/ionic liquid functionalized graphene oxide nanocomposite membrane for alkaline anion exchange membrane fuel cells. Mater Lett 173:219–222

    Article  Google Scholar 

  22. Liao X, Ren L, Chen D, Liu X, Zhang H (2015) Nanocomposite membranes based on quaternized polysulfone and functionalized montmorillonite for anion-exchange membranes. J Power Sources 286:258–263

    Article  Google Scholar 

  23. Yang Chun-Chen, Chiu Sheng-Shin, Kuo Shih-Chen, Liou Tzong-Horng (2012) Fabrication of anion-exchange composite membranes for alkaline direct methanol fuel cells. J Power Sources 199:37–45

    Article  Google Scholar 

  24. Chen D, Hickner MA (2013) Ion clustering in quaternary ammonium functionalized benzylmethyl containing poly(arylene ether ketone)s. Macromolecules 46:9270–9278

    Article  Google Scholar 

  25. Wang J, Gu S, Xiong R, Zhang B, Xu B, Yan Y (2015) Structure-property relationships in hydroxide-exchange membranes with cation strings and high ion-exchange capacity. ChemSusChem 8:4229–4234

    Article  Google Scholar 

  26. Rit A, Pape T, Hahn FE (2010) Self-assembly of molecular cylinders from polycarbene ligands and AgI or AuI. J Am Chem Soc 132:4572–4573

    Article  Google Scholar 

  27. Fan J, Gan L, Kawaguchi H, Sun W-Y, Yu KB, Tang WX (2003) Reversible anion exchanges between the layered organic–inorganic hybridized architectures: syntheses and structures of manganese(II) and copper(II) complexes containing novel tripodal ligands. Chem Eur J 9:3965–3973

    Article  Google Scholar 

  28. Li YL, Hua JA, Zhao Y, Kang YS, Sun WY (2015) Metal-organic frameworks with 1,3,5-tris(1-imidazolyl)benzene and dicarboxylate ligands: synthesis, anion exchange and gas adsorption. Microporous Mesoporous Mater 214:188–194

    Article  Google Scholar 

  29. Li N, Wang L, Hickner M (2014) Cross-linked comb-shaped anion exchange membranes with high base stability. Chem Commun 50:4092–4095

    Article  Google Scholar 

  30. Schauer J, Hnát J, Brožová L, Žitka J, Bouzek K (2015) Anionic catalyst binders based on trimethylamine-quaternized poly(2,6-dimethyl-1,4-phenylene oxide) for alkaline electrolyzers. J Membr Sci 473:267–273

    Article  Google Scholar 

  31. Zhu L, Zimudzi TJ, Wang Y, Yu X, Pan J, Han J, Kushner DI, Zhuang L, Hickner MA (2017) Mechanically robust anion exchange membranes via long hydrophilic cross-linkers. Macromolecules 50:2329–2337

    Article  Google Scholar 

  32. Yang Y, Sun N, Sun P, Zheng L (2016) Effect of the bis-imidazolium-based poly (ionic liquid) on the microstructure and the properties of AAEMs based on polyvinyl alcohol. RSC Adv 6:25311–25318

    Article  Google Scholar 

  33. Li MY, Zhang G, Xu S, Zhao CJ, Han MM, Zhang LY (2014) Cross-linked polyelectrolyte for direct methanol fuel cells applications based on a novel sulfonated cross-linker. J Power Sources 255:101–107

    Article  Google Scholar 

  34. Olsson JS, Pham TH, Jannasch P (2017) Poly(N, N-diallylazacycloalkane)s for anion-exchange membranes functionalized with n-spirocyclic quaternary ammonium cations. Macromolecules 50:2784–2793

    Article  Google Scholar 

  35. Wu L, Pan Q, Varcoe JR, Zhou D, Ran J, Yang Z, Xu T (2015) Thermal crosslinking of an alkaline anion exchange membrane bearing unsaturated side chains. J Membr Sci 490:1–8

    Article  Google Scholar 

  36. Dang HS, Jannasch P (2015) Exploring different cationic alkyl side chain designs for enhanced alkaline stability and hydroxide ion conductivity of anion-exchange membranes. Macromolecules 48:5742–5751

    Article  Google Scholar 

  37. Han J, Zhu L, Pan J, Zimudzi TJ, Wang Y, Peng Y, Hickner MA, Zhuang L (2017) Elastic long-chain multication cross-linked anion exchange membranes. Macromolecules 50:3323–3332

    Article  Google Scholar 

  38. Ponce-González J, Whelligan DK, Wang L, Bance-Soualhi R, Wang Y, Peng Y, Peng H, Apperley DC, Sarode HN, Pandey TP, Divekar AG, Seifert S, Herring AM, Zhuang L, Varcoe JR (2016) High performance aliphatic-heterocyclic benzyl-quaternary ammonium radiation-grafted anion-exchange membranes. Energy Environ Sci 9:3724–3735

    Article  Google Scholar 

  39. Wang L, Magliocca E, Cunningham EL, Mustain WE, Poynton SD, Escudero-Cid R, Nasef MM, Ponce-González J, Bance-Souahli R, Slade RCT, Whelligan DK, Varcoe JR (2017) An optimised synthesis of high performance radiation-grafted anion-exchange membranes. Green Chem 19:831–843

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully appreciate the financial support from the National Key Research and Development Program of China (Program No. 2016YFB0101200 (2016YFB0101203)), the National Natural Science Foundation of China (No. 21376022 and 21276021), the International S&T Cooperation Program of China (No. 2013DFA51860) and the Fundamental Research Funds for the Central Universities (No. JC1504).

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Authors and Affiliations

  1. State Key Laboratory of Chemical Resource Engineering, Institute of Modern Catalysis, Department of Organic Chemistry, Beijing University of Chemical Technology, Beijing, 100029, People’s Republic of China

    Hong Zhu, Rui Li, Fanghui Wang, Nanjun Chen, Ziming Li & Zhiqian Wang

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  1. Hong Zhu
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  2. Rui Li
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  3. Fanghui Wang
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Correspondence to Zhiqian Wang.

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Zhu, H., Li, R., Wang, F. et al. Poly tris (1-imidazolyl) benzene ionic liquids/Poly (2,6-dimethyl phenylene oxide) composite membranes for anion exchange membrane fuel cells. J Mater Sci 52, 11109–11119 (2017). https://doi.org/10.1007/s10853-017-1270-8

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