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Synthesis and Characterization of Sulfonated Poly(Phenylene) Containing a Non-Planar Structure and Dibenzoyl Groups

Author

Listed:
  • Hohyoun Jang

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Sabuj Chandra Sutradhar

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Jiho Yoo

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Jaeseong Ha

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Jaeseung Pyo

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Chaekyun Lee

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Taewook Ryu

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

  • Whangi Kim

    (Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea)

Abstract

Polymers for application as sulfonated polyphenylene membranes were prepared by nickel-catalyzed carbon-carbon coupling reaction of bis(4-chlorophenyl)-1,2-diphenylethylene (BCD) and 1,4-dichloro-2,5-dibenzoylbenzene (DCBP). Conjugated cis/trans isomer (BCD) had a non-planar conformation containing four peripheral aromatic rings that facilitate the formation of π–π interactions. 1,4-Dichloro-2,5-dibenzoylbenzene was synthesized from the oxidation reaction of 2,5-dichloro- p -xylene, followed by Friedel-Crafts reaction with benzene. DCBP monomer had good reactivity in polymerization affecting the activity of benzophenone as an electron-withdrawing group. The polyphenylene was sulfonated using concentrated sulfuric acid. These polymers without any ether linkages on the polymer backbone were protected from nucleophilic attack by hydrogen peroxide, hydroxide anion, and radicals generated by polymer electrolyte membrane fuel cell (PEMFC) operation systems. The mole fraction of the sulfonic acid groups was controlled by varying the mole ratio of bis(4-chlorophenyl)-1,2-diphenylethylene in the copolymer. In comparison with Nafion 211 ® membrane, these SBCDCBP membranes showed ion exchange capacity (IEC) ranging from 1.04 to 2.07 meq./g, water uptake from 36.5% to 69.4%, proton conductivity from 58.7 to 101.9 mS/cm, and high thermal stability.

Suggested Citation

  • Hohyoun Jang & Sabuj Chandra Sutradhar & Jiho Yoo & Jaeseong Ha & Jaeseung Pyo & Chaekyun Lee & Taewook Ryu & Whangi Kim, 2016. "Synthesis and Characterization of Sulfonated Poly(Phenylene) Containing a Non-Planar Structure and Dibenzoyl Groups," Energies, MDPI, vol. 9(2), pages 1-11, February.
    • Handle: RePEc:gam:jeners:v:9:y:2016:i:2:p:115-:d:64021
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    Citations

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    Cited by:

    1. Devin Fowler & Vladimir Gurau & Daniel Cox, 2019. "Bridging the Gap between Automated Manufacturing of Fuel Cell Components and Robotic Assembly of Fuel Cell Stacks," Energies, MDPI, vol. 12(19), pages 1-14, September.
    2. Mirko Sgambetterra & Sergio Brutti & Valentina Allodi & Gino Mariotto & Stefania Panero & Maria Assunta Navarra, 2016. "Critical Filler Concentration in Sulfated Titania-Added Nafion™ Membranes for Fuel Cell Applications," Energies, MDPI, vol. 9(4), pages 1-15, April.

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