Poly(arylene ether)s and poly(arylene thioether)s containing the 1,2-dihydro-4-phenyl(2H)- phthalazinone moiety

Ding, Yong; Hlil, Antisar R.; Hay, Allan S.

doi:10.1002/(sici)1099-0518(199802)36:3<455::aid-pola9>3.0.co;2-q

Cited by 22 publications

(3 citation statements)

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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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“…The electron impact (EI) source is useful for the study of intramolecular rearrangements, because the fragmentation processes under EI conditions are unimolecular processes. One such intramolecular rearrangement is the Newman‐Kwart rearrangement of O ‐aryl dialkylthiocarbamates found under solution‐phase conditions 6–14. A number of phenols have been converted to the corresponding thiol compounds by exploiting the Newman‐Kwart rearrangement (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Mass spectral study of O‐ and S‐aryl dimethylthiocarbamates under electron impact conditions: Newman‐Kwart rearrangement in the gas phase

Prabhakar

Kar

Mirza

et al. 2001

Rapid Comm Mass Spectrometry

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The electron impact (EI) mass spectra of isomeric S-and O-aryl (2-naphthyl, R-Ph-= aryl, where R = H, NO 2 , COOCH 3 , COCH 3 and OCH 3 ) dimethylthiocarbamates have been studied in detail. The EI spectra of O-aryl dimethylthiocarbamates include some of the fragment ions that are characteristic of the corresponding S-aryl isomer, which could be explained by a Newman-Kwart rearrangement in the ion source of the mass spectrometer, after ionization. The EI mass spectra of S-aryl dimethylthiocarbamates showed specific fragment ions resulting from cleavage of the molecular ion involving the bond between sulfur and the carbonyl group of the carbamate moiety (a-cleavage). The EI mass spectra of O-aryl dimethylthiocarbamates, however, showed the fragmentation of the molecular ion by a-cleavage involving the bonds on both sides of oxygen atom. Further, the EI mass spectra of O-aryl dimethylthiocarbamates containing an electron-withdrawing substituent (-R) on the aryl group showed a characteristic fragment ion corresponding to [M À R] . Copyright # 2001John Wiley & Sons, Ltd.Mass spectrometry continues to be a sensitive tool not only for the characterization of compounds of different nature, but also for the study of gas-phase reactions. Rearrangement reactions play a major role in the solution phase, which can sometimes be a direct pathway for critical transformations. Many solution-phase rearrangements are also studied in the ion source of a mass spectrometer, a procedure suitable for exploring the fundamental nature of the rearrangements in the absence of solvent. 1±5 The electron impact (EI) source is useful for the study of intramolecular rearrangements, because the fragmentation processes under EI conditions are unimolecular processes. One such intramolecular rearrangement is the Newman-Kwart rearrangement of O-aryl dialkylthiocarbamates found under solution-phase conditions. 6±14 A number of phenols have been converted to the corresponding thiol compounds by exploiting the NewmanKwart rearrangement (Scheme 1). Mass spectral analyses of reaction products of the Newman-Kwart rearrangement have not been reported in the literature, to our knowledge. Hence, a detailed study of the behaviour of isomeric S-aryl and O-aryl dimethylthiocarbamates under EI conditions was undertaken, and the results are presented. EXPERIMENTALThe S-aryl dimethylthiocarbamates (1, 3, 5, 7 and 9; Scheme 2) were prepared from the corresponding O-aryl dimethylthiocarbamates (2, 4, 6, 8 and 10; Scheme 2) under microwave irradiation. 15 The structures of all the compounds were characterized by IR, NMR and mass spectrometry. Mass spectra were recorded using a Micromass Autospec M mass spectrometer equipped with an OPUS V3.IX data system, using a dedicated EI source. The source conditions were: accelerating voltage 7 kV, electron energy 70 eV, trap current 200 mA, and source temperature 250°C. Spectra were acquired using the data system with a scan time of 1s/decade and 0.5 s interscan delay. All the samples were introduced through an HP 5890 seri...

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“…17 The phenolate anion and the aza-nitrogen anion, formed by reaction with potassium carbonate as a base, underwent a nucleophilic displacement reaction with pchloronitrobenzene to yield the dinitro compound 2 in a 92% yield. Subsequent hydrogenation with hydrazine monohydrate/Pd-C gave a novel diamine monomer 3.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of all-aromatic polyamides containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety

Jian

Cheng

1999

J. Polym. Sci. A Polym. Chem.

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Poly(arylene ether)s and poly(arylene thioether)s containing the 1,2-dihydro-4-phenyl(2H)- phthalazinone moiety

Cited by 22 publications

References 6 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

Mass spectral study of O‐ and S‐aryl dimethylthiocarbamates under electron impact conditions: Newman‐Kwart rearrangement in the gas phase

Synthesis of all-aromatic polyamides containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety

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