cas 25067-59-8, Poly(N-vinylcarbazole) | Articles data

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Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
Bienewald, Frank,Comba, Peter,Hashmi, A. Stephen K.,Menche, Maximilian,Rominger, Frank,Schafer, Ansgar,Schaub, Thomas,Sitte, Nikolai A.,Tuzina, Pavel
p. 13041 - 13055
(2021/09/18)

Base-Mediated Site-Selective Hydroamination of Alkenes
We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.
Koh, Ming Joo,Lee, Boon Chong,Li, Ping,Zhang, Xiaoxiang
supporting information

(2021/12/29)

Polymer, and mixture or formulation, and organic electronic device containing same, and monomer thereof
Disclosed are a polymer, and a mixture or a formulation and an organic electronic device containing same, and applications thereof, and further a monomer of which the polymer is made; the polymer comprises on its side chain a repeating structure unit E, characterizing in that its S1(E)?T1(E))≤0.35 eV or even less, which may allow the said polymer having thermally activated delayed fluorescence (TADF) property. Thus a TADF polymer suitable for printing processes is provided, thereby reducing OLED manufacturing costs.
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(2020/11/23)

Method for synthesizing N-vinylcarbazole
The invention provides a novel method for synthesizing N-vinylcarbazole, and belongs to the field of organic synthesis. The method comprises the steps that under the KOH alkaline condition, carbazoleand methylbutynol react in an ethanol solvent to generate the N-vinylcarbazole, and the reaction temperature is 75-80 DEG C. The novel method has the advantages of mild condition, easy and convenientoperation, safety, low cost, high yield and the like.
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Paragraph 0014-0019

(2019/11/13)

Method for preparing N-vinyl carbazole
The invention discloses a method for preparing N-vinyl carbazole and in particular discloses a method for preparing N-vinyl carbazole under catalysis of a solid super-strength base catalyst. The method comprises the following steps: uniformly mixing carbazole, a supported solid super-strength base catalyst and a solvent at the room temperature, heating to 130-150 DEG C to carry out a backflow reaction, continuously introducing an acetylene gas which has a flowing velocity of 20-60mL/minute, controlling that slight bubbles are generated from the liquid level inside the reaction system, carryingout a reaction for 7-10 hours, cooling to the room temperature, filtering, further carrying out vacuum distillation on a liquid phase at 150-160 DEG C, thereby obtaining N-vinyl carbazole. The methodis simple to operate, gentle in condition, high in yield, convenient in catalyst recycling and reuse and good in application prospect.
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Paragraph 0029; 0031; 0033; 0037; 0041

(2018/12/02)

Vinylation of a secondary amine core with calcium carbide for efficient post-modification and access to polymeric materials
We developed a simple and efficient strategy to access N-vinyl secondary amines of various naturally occurring materials using readily available solid acetylene reagents (calcium carbide, KF, and KOH). Pyrrole, pyrazole, indoles, carbazoles, and diarylamines were successfully vinylated in good yields. Cross-linked and linear polymers were synthesized from N-vinyl carbazoles through free radical and cationic polymerization. Post-modification of olanzapine (an antipsychotic drug substance) was successfully performed.
Rodygin, Konstantin S.,Bogachenkov, Alexander S.,Ananikov, Valentine P.
(2018/03/29)

Substrate-Controlled Regio- and Stereoselective Synthesis of (Z)- and (E)- N-Styrylated Carbazoles, Aza-carbazoles, and γ-Carbolines via Hydroamination of Alkynes
We report herein the substrate-controlled regio- and stereoselective hydroamination of carbazoles, aza-carbazoles, and γ-carbolines with functionalized aromatic as well as aliphatic alkynes in a KOH/DMSO system in good yields. The electronic effect of the substrates governs the stereochemistry of the product. Electron-donating alkynes provided (Z)-stereoselective products, and electron-withdrawing alkynes provided (E)-stereoselective products. This approach also provides an easy route for the synthesis of mono- and bis-hydroaminated product. The deuterium-labeling studies were also conducted to support the mechanistic pathway.
Garg, Vineeta,Kumar, Pradeep,Verma, Akhilesh K.
p. 11686 - 11702
(2018/09/21)

Large Pi conjugated silicozine derivative and organic light-emitting device using same
The invention provides a large Pi conjugated silicozine derivative and an organic light-emitting device using the same, and belongs to the technical field of organic photoelectric materials. The large Pi conjugated silicozine derivative has a structure shown by a formula (I). The organic light-emitting deice prepared by using the large Pi conjugated silicozine derivative provided by the invention is relatively high in luminous efficiency and external quantum efficiency, and relatively low in driving voltage.
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Paragraph 0040; 0041; 0042

(2017/07/04)

Compounding method for N-ethyl carbazole
The invention provides a compounding method for N-ethyl carbazole and relates to N-ethyl carbazole. The method comprises the following steps: performing salt-forming reaction on carbazole and proton-removing agent in an N-methyl pyrrolidone solvent, thereby generating carbazole salt; continuing introducing acetylene and reacting, thereby acquiring N-vinyl carbazole; adding a Pd catalyst into the organic solvent of the generated N-vinyl carbazole and performing hydrogenation reaction in the additives, thereby acquiring N-ethyl carbazole. A series of special catalysts are optimized, a catalytic hydrogenation technology is adopted for effectively realizing the green synthesis of N-ethyl carbazole and three-waste emission is reduced. In a hydrogenation process, the catalyst is reusable and the cost is lowered. The quality of the N-ethyl carbazole product prepared according to the hydrogenation process is higher. The traditional alkylate reagent (diethyl sulfate, ethyl carbonate, halothane, and the like) or the toxic organic solvent is not required, no waste liquid is emitted and the compounding method is a green and clean production technology.
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Paragraph 0023-0035

(2018/03/24)

Reactions of carbazole with dimethyl alkanedisulfonates
Reaction of carbazole with dimethyl alkanedisulfonates in the presence of sodium hydride resulted in the formation of three main products: 2-(9H-carbazol-9-yl)alkylmethanesulfonates, 1,2-di-(9H-carbazol-9-yl)alkanes, and 9-alkenyl-9H-carbazoles.
Sokolov,Aksinenko, A. Yu.,Epishina,Goreva
p. 1641 - 1644
(2017/09/01)

BICARBAZOLE COMPOUND, PHOTO-CURABLE COMPOSITION, CURED PRODUCT THEREOF, CURABLE COMPOSITION FOR PLASTIC LENS, AND PLASTIC LENS
A photopolymerizable material contains, as a main polymerization component, a bicarbazole compound represented by structural formula (1). In structural formula (1), X1 and X2 are each independently a photopolymerizable functional group, a structural site having a photopolymerizable functional group, or a hydrogen atom, at least one of X1 and X2 is a photopolymerizable functional group or a structural site having a photopolymerizable functional group, R1 and R2 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a bromine atom, or a chlorine atom, and at least one of R1 and R2 is a hydrogen atom.
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Paragraph 0100

(2017/04/04)

Iridium-Catalyzed Vinylation of Carbazole Derivatives with Vinyl Acetate
We report a practical method for the synthesis of vinylcarbazoles via iridium-catalyzed vinylation of carbazoles with vinyl acetate as the vinyl source. This simple and efficient reaction using an iridium catalyst provides a convenient method for producing monomers for the synthesis of poly(N-vinylcarbazole)s, which are used in electroluminescent devices.
Kimura, Jungo,Nakamichi, Seiya,Ogawa, Shinji,Obora, Yasushi
supporting information
p. 719 - 723
(2017/03/21)

PRODUCTION METHOD OF N-VINYL CARBAZOLE
PROBLEM TO BE SOLVED: To provide a production method of an N-vinyl carbazole to be used as a raw material for producing various chemical products including electronic information materials, battery materials, optical materials, film materials, optical film materials, organic EL materials, resist materials, liquid crystal materials, paints, adhesives, and detergents. SOLUTION: A high-purity N-vinyl carbazole can be safely and inexpensively produced by thermally decomposing a compound expressed by formula (1) at 100°C or higher in the presence of a nitrogen-containing compound having no N-H bond while generation of impurities that are difficult to be removed is suppressed and no reaction under a reduced pressure condition is required. In formula (1), R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0041-0049

(2018/11/22)

PRODUCTION METHOD OF N-VINYL CARBAZOLE
PROBLEM TO BE SOLVED: To provide a novel production method of an N-vinyl carbazole to be used as a raw material for producing various chemical products including electronic information materials, battery materials, optical materials, film materials, optical film materials, organic EL materials, resist materials, liquid crystal materials, paints, adhesives, and detergents. SOLUTION: A method for safely and inexpensively producing a high-purity N-vinyl carbazole is provided, which comprises thermally decomposing a compound expressed by formula (1) at 100°C or higher in the presence of a secondary amine that has an alkyl group having 3 to 12 carbon atoms and a branch on a carbon atom adjacent to an N atom, or in the presence of an alicyclic group having 3 to 12 carbon atoms. In formula (1), R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0045-0052

(2018/11/22)

METHOD OF PRODUCING N-VINYLCARBAZOLE
PROBLEM TO BE SOLVED: To provide a method of producing N-vinylcarbazole. SOLUTION: A compound represented by formula (1) is decomposed by heat, in the presence of at least one selected from the group consisting of metal carbonate, metal bicarbonate, and inorganic adsorbent, at 100°C or more, wherein R1 is a hydrogen atom, or a 1-4C alkyl group. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0050-0055

(2018/11/22)

METHOD OF PRODUCING N-VINYLAZOLE
PROBLEM TO BE SOLVED: To provide a method to obtain, at high yields and economically, N-vinylazoles useful as the material monomer for a functional compound such as an organic electroluminescence, an electrophotographic photoreceptor, an organic semiconductor, and a solar battery. SOLUTION: This invention provides a method to obtain, at high yields and high selectively, N-vinylazoles by making an azole and a vinyl halide react with each other in the presence of a palladium compound and a phosphorous ligand with NaOH used as a base. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0031; 0033

(2017/03/08)

Combined phase transfer catalysis and ultrasound to enhance tandem alkylation of azo dyes
Ultrasound has been found to enhance N-substitution against elimination in the reaction of carbazole-containing bromides 3 with a Disperse Orange 3 derivative 2 under PTC condition. Upon using combined PTC and ultrasound conditions, a series of bifunctional molecules 1 have been prepared to possess charge-transporting agents and nonlinear optical chromophores in 2:1 ratio.
Li, Xiang,Wang, Jie,Mason, Richard,Bu, Xiu R,Harrison, Joycelyn
p. 3747 - 3753
(2007/10/03)

Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine
(formula presented) Vinylation of various azoles (pyrrole, indole, carbazole, and their derivatives) and phenothiazine with vinyl bromides catalyzed by palladium-phosphine complexes results in the respective N-vinylazoles in 30-99% yields. This reaction w
Lebedev, Artyom Y.,Izmer, Vyatcheslav V.,Kazyul'kin, Denis N.,Beletskaya, Irina P.,Voskoboynikov, Alexander Z.
p. 623 - 626
(2007/10/03)

Synthesis of vinyl monomers with active azaaromatic groups. Phase-transfer catalytic approach
An efficient method based on the alkylation-elimination reactions under solid-liquid phase transfer-catalysis conditions (S/L PTC) is reported for the preparation of N-vinyl derivatives of azaheterocyclic compounds.
Bogdal, Dariusz,Jaskot, Krzysztof
p. 3341 - 3352
(2007/10/03)