Synthesis of All Aromatic Phthalazinone Containing Polymers by a Novel N-C Coupling Reaction

Yoshida, Shu; Hay, Allan S.

doi:10.1021/ma00111a064

Cited by 49 publications

(32 citation statements)

References 12 publications

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“…DHPZ was provided by Dalian Polymer New Material Co. Ltd., PR China and the preparation procedure was reported previously [26][27][28][29]. SDFB-Na was prepared according to the procedures described in literature [10] and elsewhere [12].…”

Section: Methodsmentioning

confidence: 99%

Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials

Gao

Robertson

Guiver

et al. 2006

Journal of Membrane Science

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Sulfonated poly(phthalazinone ether ketone nitrile) copolymers (SPPEKN) were prepared by copolymerization of disodium 3,3′ -disulfonate-4,4′ -difluorobenzophenone (SDFB-Na), 2,6-difluorobenzonitrile (2,6-DFBN), and 4-(4-hydroxyphenyl)-1(2H)-phthalazinone (DHPZ) at 160• C in N-methyl-2-pyrrolidione containing anhydrous potassium carbonate. The polymerization reactions proceeded smoothly and in high yield giving high molecular weight SPPEKN copolymers with different sulfonic acid content (SC) values. The polymer structures were defined by 1 H NMR and FT-IR. Membrane films of SPPEKN copolymers in both salt and acid forms, prepared at SDFB-Na to 2,6-DFBN feed ratios up to 60/40 mol/mol, were cast from the N,N-dimethylacetamide (DMAc) polymer solutions. The presence of highly polar nitrile groups are expected to increase interchain molecular forces, contributing to the observed reduction in water swelling over previously prepared sulfonated poly(phthalazinone ether ketone) (SPPEK) copolymers. Membranes containing nitrile groups are expected to show improved adhesion between polymer and catalyst when utilized in a fuel cell. All SPPEKN copolymers exhibited tensile strength higher than that of Nafion ® 117. The proton conductivities of acid form SPPEKN copolymers (SPPEKNH)s, prepared at the sulfonated/unsulfonated monomer feed ratio above 0.35 mol/mol, were around 10 −1 S/cm at 80• C, which is close to or higher than that of Nafion ® 117 under same measurement conditions.

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Section: Methodsmentioning

confidence: 99%

Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials

Gao

Robertson

Guiver

et al. 2006

Journal of Membrane Science

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“…These polymers with rigid unsymmetrical phthalazinone moieties [23] showed favorable cell performance in VRFB systems.…”

Section: Introductionmentioning

confidence: 99%

Low vanadium ion permeabilities of sulfonated poly(phthalazinone ether ketone)s provide high efficiency and stability for vanadium redox flow batteries

Chen

Zhang

Chen

et al. 2017

Journal of Power Sources

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“…2,3 Pioneering work of phthalazinone resins was disclosed by Hay and Berard in 1993, 4 and then a number of organosoluble phthalazinone resins including aromatic polyethers, polyamides, polyimides and polyesters have been developed by Hays' group and our group. 5,6 Most of our research efforts have evolved around molecular engineering including designing of novel phthalazinone monomers and polymers with various kinds of structures, 7 tailoring the performance and processing properties as well as investigating the structure-property relationship 8 along with their utilities in structural materials such as electronic, marine and aerospace industries. 9 Based on our research it is accepted that the introduction of phthalazinone moieties along the rigid-rod polymer main chain can increase the solubility without sacrificing thermal stability and mechanical property.…”

Section: Introductionmentioning

confidence: 99%

Highly thermostable rigid-rod networks constructed from an unsymmetrical bisphthalonitrile bearing phthalazinone moieties

Liu

et al. 2012

Polym. Chem.

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Phthalazinone rigid-rod networks with excellent thermostability have been prepared by the polyaddition of an unsymmetrical phthalonitrile-functional phthalazinone, namely 4-(4-(4-(3,4-dicyanophenoxy)phenyl)-1-oxophthalazin-2(1H)-yl)phthalonitrile (5) in the presence of promoting agents. 5 was readily prepared via nucleophilic displacement of 4-(4-hydroxylphenyl)(2H)-phthalazin-1-one (1) with 4-nitrophthalonitrile (3) under mild conditions. The substitution of N-H in phthalazinone was accomplished via a novel N-C coupling reaction in an essentially quantitative yield, confirmed by spectroscopic studies as well as a model reaction of 4-(4-tolyl)(2H)-phthalazin-1-one (2). Green prepolymers (7a-7c) were obtained by the polymerization of 5 in its melt phase with the charge of aromatic diamines (6a-6c), and with concurrent cyclization a mixture of poly(iminoisoindolenine) oligomers was produced. The obtained amorphous 7a-7c show T g s ranging from 180 to 190 C depending on the amine nature. Both 5 and 7a-7c have a non-coplanar conformation and exhibit sufficiently good solubility in common solvents (e.g., DMSO, DMF, DMAc, NMP, CHCl 3 , etc.), and hence can be processed either from their melt or from solution. The insoluble networks (8a-8c) prepared by direct curing of 5 or by post-curing of 7a-7c exhibit excellent thermal properties together with superior long-term thermo-oxidative stabilities.

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Synthesis of All Aromatic Phthalazinone Containing Polymers by a Novel N-C Coupling Reaction

Cited by 49 publications

References 12 publications

Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials

Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials

Low vanadium ion permeabilities of sulfonated poly(phthalazinone ether ketone)s provide high efficiency and stability for vanadium redox flow batteries

Highly thermostable rigid-rod networks constructed from an unsymmetrical bisphthalonitrile bearing phthalazinone moieties

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