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

Hohyoun Jang, Sabuj Chandra Sutradhar, Jiho Yoo, Jaeseong Ha, Jaeseung Pyo, Chaekyun Lee, Taewook Ryu and Whangi Kim
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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

Energies, 2016, vol. 9, issue 2, 1-11

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 ?–? 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.

Keywords: PEMFC; ?–? interaction; proton conductivity; carbon-carbon coupling; nickel catalyst (search for similar items in EconPapers)
JEL-codes: Q Q0 Q4 Q40 Q41 Q42 Q43 Q47 Q48 Q49 (search for similar items in EconPapers)
Date: 2016
References: View complete reference list from CitEc
Citations: View citations in EconPapers (2)

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