NN bonded polymers

Jain, Sanjay; Sridhara, K.; Thangamathesvaran, P. M.

doi:10.1016/0079-6700(93)90024-7

Cited by 21 publications

(7 citation statements)

References 90 publications

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“…Nitrogen-nitrogen bonds are prevalent in natural products, 1 pharmaceuticals, 2 and organic materials 3 (Scheme 1A). Various methods are available to prepare these bonds, with classical methods including diazotization of anilines with sodium nitrite and a Brønsted acid, and the use of N -chlorinated reagents or related electrophilic nitrogen species.…”

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confidence: 99%

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

2018

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A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N-N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O, 60-80 °C) with a catalyst composed of CuBr·dimethylsulfide and N, N-dimethylaminopyridine. Reactions between carbazole and diarylamines show unusually selective cross-coupling, even with a 1:1 ratio of the two substrates. This behavior was found to arise from reversible formation of the tetraarylhydrazine. Formation of this species is kinetically favored, but cleavage of the N-N bond under the reaction conditions leads to selective formation of the thermodynamically favored cross-coupling product.

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Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

2018

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“…Polymers with the N-N bond in the polymer chain,6 as well as polymers whose heterocycle contains the N-N linkage, have been previously synthesized. 7 Imai reported the synthesis of poly(pyridazinophthalazinedione)s, which have high thermostability, from dibenzoylphthalic acids and bis(aryl)hydrazines.8…”

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

Yoshida¹,

Hay²

1995

Macromolecules

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“…Polymers with the N−N bond in the polymer chain as well as polymers whose heterocyclic ring contains the N−N linkage have been previously synthesized. However, there are very few reports about the synthesis of phthalazinone-containing polymers in the literature.…”

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

Yoshida

Hay

1997

Macromolecules

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High molecular weight poly(phthalazinone)s with high glass transition temperatures were prepared by a novel N−C coupling reaction. New bis(phthalazinone) monomers (5a−f), such as 7,7‘-oxobis[4-phenylphthalazin-1(2H)-one] (5c), were synthesized from the corresponding bis(phthalic anhydride)s (3a−f) in two steps. Other types of bis(phthalazinone) monomers (8, 9) were synthesized from phthalic anhydride and diphenyl sulfide or diphenyl ether. AB-type phthalazinone monomers (11a, 12−14) were also synthesized from phthalic anhydride. Poly(phthalazinone)s, having inherent viscosities of 0.3−0.4 dL/g, were prepared by the reaction of the bis(phthalazinone) monomers with an activated aryl halide such as bis(4-fluorophenyl) sulfone (22) in a dipolar aprotic solvent in the presence of potassium carbonate. AB-type phthalazinone monomers do not form high molecular weight polymers because of premature precipitation during the polymerization reaction. One of the AB-type phthalazinone monomers, 4-[4-((4-fluorophenyl)sulfonyl)phenyl]phthalazin-1(2H)-one, was successfully copolymerized with 4,4‘-biphenol and bis(4-fluorophenyl) sulfone to form high molecular weight polymers. The copolymers showed higher glass transition temperatures (T gs) as the phthalazinone ratio increased. All phthalazinone homopolymers except the Bisphenol A phthalazinone polymers show T gs around 300 °C by differential scanning calorimetry. The decomposition temperatures for 5% weight losses in air and in nitrogen measured by thermogravimetric analysis are in the range of 480−530 °C. Polymers from the Bisphenol A phthalazinone monomer are soluble in chlorinated solvents such as chloroform. Other polymers are soluble in dipolar aprotic solvents such as N-methyl-2-pyrrolidinone. The soluble polymers can be cast into flexible films from solution.

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NN bonded polymers

Cited by 21 publications

References 90 publications

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling

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

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

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