Synthesis of polymers containing azo groups in the main chain from <Emphasis Type="Italic">m</Emphasis>-phenylenediamine: Study of doping

Synthesic approach to polymers containing azo groups was developed on the basis of diazotization and azo-coupling reaction of m-phenylenediamine (m-PDA) with various ratio m-phenylenediamine-sodium nitrite. Doping of poly(azoaminophenylenes) with iodine, perchloric and hydrochloric acids was examined. Electroconductivity increases in the case of iodine to 0.2 S mol⁻¹, of perchloric acid, to 7×10⁻³ S mol⁻¹, and at the action of hydrogen chloride it is virtually unaffected. According to the ESR spectra, at the doping with iodine and perchloric acid electroconductivity enhances generally due to the mobility increase of the charge carriers (polarons).     

β-(2-hydroxy-4-chloro-3-quinolyl)propiolactone

2,4-Dihydroxy-3-(3,3-dichloroallyl)quinoline, the corresponding 4-mono and 2,4-dichloro derivatives, and substituted -(3-quinolyl)propionic acids were synthesized. -(2-Hydroxy-4-chloro-3-quinolyl) propiolactone was obtained from the latter.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 975–977, July, 1972.     

Synthesis and investigation of poly(p-phenylenediamine)–poly(1,4-benzoquinonediimine-<Emphasis Type="Italic">N,N</Emphasis>-diyl-1,4-phenylene)

Poly(1,4-benzoquinonediimine-N,N-diyl-1,4-phenylene) having similar structure to pernigraniline was synthesized by chemical oxidative polymerization of p-phenylenediamine and its salt using potassium peroxydisulfate as an oxidant in molar ratio 1:0.8, in acetic acid, at 278 K. Acetylation of amino end groups of polymers were carried out aiming to prevent self-condensation of amino groups with 1,4-benzoquinone diimine groups by 1,4-addition. Attempting to carry out the reduction of obtained polymer with hydrazine hydrate, it was shown that 1,4-addition of hydrazine to quinonediimine groups occurs instead of expected reduction reaction. When doping obtained polymers with iodine, the electrical conductivity increases up to 10^?4 S/cm.     

Quinaldine derivatives

A new synthesis of substituted 2,5-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]quinolines is realized by heating the corresponding 2-methyl-3-(3-hydroxybutyl)-4-hydroxy(methoxy)-quinoline in polyphosphoric acid. The preparation of ketones of the quinoline series is described.See [1] for communication XXV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 534–537, April, 1972.     

Synthesis of (2-methylquinolin-4-ylsulfanyl)-substituted acetic and propionic acids and propionitriles

A procedure has been developed for the synthesis of (2-methylquinolin-4-ylsulfanyl)-substituted acetic and propionic acids and propionitriles having methyl, methoxy, or carboxy groups or halogen atom in position 6 or 8 of the quinoline ring via reactions of the corresponding substituted 2-methylquinoline-4-thiols with chloroacetic or acrylic acid and acrylonitrile.     

Synthesis of polymers containing polyaniline fragments linked by 1,4-benzoquinone groups

Russian Journal of General Chemistry - Michael reaction of 1,4-benzoquinone and N-acetyl-4,4'-diaminodiphenylamine has afforded a new polymer; hydrolysis of the latter has yielded a product...     

New derivatives of quinaldin-4-ol

The synthesis and chemical reactions of 3-(3,3-dichloroallyl)-4-hydroxy-2-methylquinoline-6-carboxylic acid, 3-(2-carboxyethyl)-4-hydroxy-2-methylquinoline-6-carboxylic acid, and of derivatives of these acids are described.For Communication XVIII, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 966–968, July, 1970.     

A dependence of electrical conductivity and some properties of paramagnetic centers on the doping level of poly(4-aminoazobenzene) with iodine

The dependences of the electrical conductivity, ESR spectral linewidths, spin concentrations, and g-factor on the level of iodine doping of poly(4-aminoazobenzene), synthesized by the oxidative polymerization of 4-aminoazobenzene with iodine, were studied for the first time. The polymers were studied by ESR and UV spectroscopy. With an increase in the level of iodine doping, the electrical conductivity of the polymers increases from 3·10⁻¹⁰ to 4·10⁻¹ S m⁻¹, the ESR linewidth increases from 0.96 to 1.94 mT, and the g-factor increases from 2.004 to 2.007. The spin concentration changes ambiguously, depending on the doping level. In the iodine-doped polymers, spins are mainly localized on two nitrogen atoms of the azo groups.     

New syntheses of N,N′-diaryl-substituted quinone diimines: I. Synthesis of N,N′-bis(4-aminophenyl)-1,4-benzoquinone diimine

Russian Journal of Organic Chemistry - Oxidative condensation of p-phenylenediamine by the action of K2S2O8 in acetic acid afforded N,N′-bis(4-aminophenyl)-1,4-benzoquinone diimine which...