25067-59-8

Basic information

• Product Name: POLY(N-VINYLCARBAZOLE)
• Synonyms: tuvical210;POLY(9-VINYLCARBAZOLE), SECONDARY STANDA RD;Poly(N-vinylcarbazole), approx. M.W. 90,000;Poly(N-vinylcarbazole), secondary standard;M.N. 56,400;Poly(N-vinylcarbazole), secondary standard, M.W. 135,600;9-Vinyl-9H-carbazole;N-VINYLCARBAZOLE POLYMER
• CAS NO: 25067-59-8
• Molecular Formula: C42H33N3X2
• Molecular Weight: 579.73
• Product Categories: Electronic Chemicals;Carbazoles;Carbazoles (for Conduting Polymer Research);Electroluminescence;Functional Materials;Reagents for Conducting Polymer Research
• Mol File: 25067-59-8.mol

Chemical Properties

• Melting Point: >300 °C
• Appearance: Off-white/powder
• Density: 1.2 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.683
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: POLY(N-VINYLCARBAZOLE)(CAS DataBase Reference)
• NIST Chemistry Reference: POLY(N-VINYLCARBAZOLE)(25067-59-8)
• EPA Substance Registry System: POLY(N-VINYLCARBAZOLE)(25067-59-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: FE6225480
• Hazardous Substances Data: 25067-59-8(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
Poly(N-vinylcarbazole) is used as a hole transporting medium for its high efficiency and low driving voltage, making it suitable for applications in the electronics industry, particularly in the fabrication of organic field effect transistors (OFETs).
Used in Energy Storage Applications:
PVK is used in the formation of nano-composite films with carbon nanospheres (CNS), which can be potentially utilized in supercapacitors. This application takes advantage of PVK's conductive properties for energy storage purposes.
Used in Sensor Applications:
The conductive nature of Poly(N-vinylcarbazole) also makes it suitable for use in sensor-based applications, where its ability to transport holes efficiently can be harnessed for detecting various stimuli.
Used in Composite Materials:
PVK can form a hybrid film when combined with graphene oxide, which can be coated on silica substrates for the fabrication of organic field effect transistors (OFETs). This highlights its potential in creating advanced composite materials for electronic applications.

Preparation

N-Vinyl carbazole may be obtained from phenylhydrazine and cyclohexanone by the following route:The second step in this synthesis is an example of the Fischer indole synthesis. Carbazole also occurs in coal tar. Poly(vinyl carbazole) is produced by adiabatic bulk polymerization under nitrogen pressure using azobisisobutyronitrile and di-tert-butyl peroxide as initiators. Heating to 80-90°C causes an onset of polymerization and a rapid increase in temperature. After the maximum temperature has been reached the mass is cooled under pressure.Poly(vinyl carbazole) is a very brittle material with a high softening point (about 195°C Vicat). It is insoluble in most organic solvents except aromatic and chlorinated hydrocarbons and tetrahydrofuran. The polymer is difficult to mould, requiring high process temperatures, namely about 300°C for injection moulding and 250°C for compression moulding. More usually the material is cast as thin film from solution. The most significant property of poly(vinyl carbazole) is its high photoconductivity and this has resulted in widespread use of the polymer in electrostatic dry-copying machines. When an electrostatic charge is applied to the polymer in the dark it discharges to an equilibrium value but when the polymer is illuminated almost complete discharging occurs. This phenomenon is used to create a latent electrostatic image which is then developed by transferring the charge to the toner. Poly(vinyl carbazole) also has good electrical insulation characteristics which are maintained over a wide range of temperature and frequency. On account of these characteristics, the polymer has been used as a capacitor dielectric, but this application is now of minor importance.

Purification Methods

Precipitate it seven times from tetrahydrofuran with MeOH, with final freeze-drying from *benzene. Dry it under vacuum.

InChI:InChI=1/C14H11N/c1-2-15-13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h2-10H,1H2

Upstream product

• 75-01-4 chloroethylene 
• 33650-07-6 potassium carbazole 
• 593-60-2 Vinyl bromide 
• 86-74-8 9H-carbazole 
• 588-73-8 (Z)-β-bromostyrene 
• 74-86-2 acetylene 
• 1484-14-6 2-carbazol-9-yl-ethanol 
• 39027-95-7 9H-carbazole-9-carbaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 4901-29-5 9-(1-acetoxyethyl)carbazole 
• 1066-54-2 trimethylsilylacetylene 
• 75-20-7 calcium carbide 
• 4672-49-5 1,2-bis(methanesulfonyloxy)ethane 

Downstream Products

• 608534-41-4 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-9H-carbazole 
• 1190639-25-8 C₁₂H₈NCH₂CH(B(O₂C₆H₄))2 
• 1449412-11-6 Mo(NAr)(CHCarbaz)(Me₂Pyr)(OTPP) 
• 5337-01-9 N-(2-cyanoethyl)carbazole 
• 15657-91-7 N-(2-hydroxyethyl)carbazolyl methacrylate 
• 6915-68-0 2-(9-carbazolyl)ethyl acrylate 
• 147425-92-1 9-[1-Benzotriazol-1-yl-3-morpholin-4-yl-1-(p-tolyl-trimethylsilanyloxy-methyl)-propyl]-9H-carbazole 
• 147425-93-2 9-[1-Benzotriazol-1-yl-1-(cyclohexyl-trimethylsilanyloxy-methyl)-3-morpholin-4-yl-propyl]-9H-carbazole 
• 147425-91-0 9-[1-Benzotriazol-1-yl-3-morpholin-4-yl-1-(phenyl-trimethylsilanyloxy-methyl)-propyl]-9H-carbazole 
• 147425-88-5 9-[1-Benzotriazol-1-yl-1-(4-methyl-benzyl)-3-morpholin-4-yl-propyl]-9H-carbazole 
• 147425-87-4 9-(1-Benzotriazol-1-yl-1-benzyl-3-morpholin-4-yl-propyl)-9H-carbazole 
• 147425-94-3 9-(1-Benzotriazol-1-yl-1-benzyl-3-pyrrolidin-1-yl-propyl)-9H-carbazole 
• 1484-14-6 2-carbazol-9-yl-ethanol 
• 101212-70-8 4-benzoyl-6-carbazol-9-yl-2-phenyl-5,6-dihydro-4H-[1,3,4]oxadiazine 

Relevant articles and documents

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.