Quaternary ammonium functionalized poly(arylene ether)s (QPAEs) containing 2,2′,6,6′-tetramethylbiphenol moieties were designed and successfully synthesized via nucleophilic substitution polycondensation, bromination, quaternization and alkalization. The structure, water uptake, ion exchange capacities (IECs), hydroxide ion conductivities, and mechanical properties, as well as thermal and chemical stabilities of obtained QPAEs membranes were investigated. The QPAE-a membrane with IEC value of 0.98 meq g⁻¹ demonstrated the highest ion conductivity (47.4 mS cm⁻¹) at 80°C. The ion transport activation energy (E_a) of QPAEs membranes varied from 8.57 to 19.95 kJ mol⁻¹. After chemical stability test conditioned in 1M NaOH at 60°C for 7 days, the QPAEs membranes except QPAE-c (IEC = 0.88 meq g⁻¹) still exhibited high hydroxide ion conductivities (over 15 mS cm⁻¹) and acceptable tensile strength (∼10 MPa). These properties indicate that the ionomers membranes are potential candidates for anion exchange membranes in anion exchange membrane fuel cells. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41525.

Four different fluorinated methyl- and phenyl-substituted 4-(4-hydroxyphenyl)-2-(pentafluorophenyl)-phthalazin-1(2H)-ones, AB-type phthalazinone monomers, have been successfully synthesized by nucleophilic addition–elimination reactions of methyl- and phenyl-substituted 2-((4-hydroxy)benzoyl)benzoic acid with 1-(pentafluorophenyl)hydrazine. Under mild reaction conditions, the AB-type monomers underwent self-condensation polymerization reactions successfully and gave fluorinated poly(phthalazinone ether)s with high molecular weights. Detailed structural characterization of the AB-type monomers and fluorinated polymers was determined by ¹H NMR, ¹⁹F NMR, FTIR, and GPC. The solubility, thermal properties, mechanical properties, water contact angles, and optical absorption of the polymers were evaluated. The polymers had high T_gs varying from 337 to 349 °C and decomposition temperatures (T_{d, 25} wt %) above 409 °C. Tough, flexible films were cast from THF and chloroform solutions. The films showed excellent tensile strengths ranging from 70 to 85 MPa with good hydrophobicities with water contact angles higher than 95.5 °C. The polymers had absorption edges below 340 nm and very low absorbance per cm at higher wavelengths 500–2500 nm. These results indicate that the polymers are promising as high performance materials, for example, membranes and hydrophobic materials. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1761–1770

Two series of sulfonated multiblock copoly(ether-ketone)s containing phthalazinone ether ketone and fluorene ether ketone moieties have been synthesized successfully by two-step polycondensation. The water uptakes of the copolymers with varying sized sulfonated poly(phthalazinone ether ketone) block as hydrophilic blocks are moderate. In this series, polymer 10a gave the proton conductivity of 1.20 × 10⁻³ S/cm with IEC of 1.03. The water uptakes of the copolymers with varying sized sulfonated poly(fluorene ether ketone) blocks as hydrophilic blocks are high than 300%. These copolymers showed better proton conductivity. The copolymers with sulfonated poly(phthalazinone ether ketone) blocks had strong alcohol resistance at refluxing temperature. Whereas the copolymers containing sulfonated poly(fluorene ether ketone) hydrophilic blocks were dissolved in methanol and ethanol. The cast films of the title ionomers were transparent, ductile, and flexible. Moreover, these copolymers demonstrated greatly improved oxidative and thermal stabilities. Especially, the copolymers comprising sulfonated poly(phthalazinone ether ketone) hydrophilic blocks and poly(fluorene ether ketone) hydrophobic blocks is a promising proton exchange membrane material for proton exchange membrane fuel cell used methanol or ethanol as fuel. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010