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Energies 2016, 9(2), 115; doi:10.3390/en9020115

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

Department of Applied Chemistry, Konkuk University, Chungju 380-701, Korea
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Academic Editor: Vladimir Gurau
Received: 16 December 2015 / Revised: 15 February 2016 / Accepted: 15 February 2016 / Published: 18 February 2016
(This article belongs to the Special Issue Polymer Electrolyte Membrane Fuel Cells 2016)
View Full-Text   |   Download PDF [4098 KB, uploaded 18 February 2016]   |  

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. View Full-Text
Keywords: PEMFC; π–π interaction; proton conductivity; carbon-carbon coupling; nickel catalyst PEMFC; π–π interaction; proton conductivity; carbon-carbon coupling; nickel catalyst
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Jang, H.; Sutradhar, S.C.; Yoo, J.; Ha, J.; Pyo, J.; Lee, C.; Ryu, T.; Kim, W. Synthesis and Characterization of Sulfonated Poly(Phenylene) Containing a Non-Planar Structure and Dibenzoyl Groups. Energies 2016, 9, 115.

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