344782-48-5

Basic information

• Product Name: 4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP&
• Synonyms: N4,N4'-bis(4-broMophenyl)-N4,N4'-diphenylbiphenyl-4,4'-diaMine;N4,N4'-Bis(4-broMophenyl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diaMine;4,4'-Bis[(p-bromophenyl)phenylamino]biphenyl;N,N'-Diphenyl-N,N'-bis(4-bromophenyl)biphenyl-4,4'-diamine
• CAS NO: 344782-48-5
• Molecular Formula: C₃₆H₂₆Br₂N₂
• Molecular Weight: 646.423
• Product Categories: Organic Electronics and Photonics;Synthetic Intermediates;Synthetic Tools and Reagents
• Mol File: 344782-48-5.mol

Chemical Properties

• Melting Point: 103-135 °C (polymorphic)
• Boiling Point: 721.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.438±0.06 g/cm3(Predicted)
• PKA: -3.33±0.60(Predicted)
• CAS DataBase Reference: 4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP&(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP&(344782-48-5)
• EPA Substance Registry System: 4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP&(344782-48-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 344782-48-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronic Materials Industry:
4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP& is used as a building block for the synthesis of organic light-emitting diodes (OLEDs) due to its efficient light emission properties, contributing to the development of advanced display technologies.
4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP& is also used as a component in the synthesis of organic photovoltaics (OPVs), leveraging its good charge transport properties to enhance the performance of solar energy conversion devices.
Furthermore, 4,4'-BIS((4-BROMOPHENYL)PHENYLAMINO)BIP& is utilized in the development of organic field-effect transistors (OFETs), where its thermal stability and charge transport characteristics are crucial for the creation of high-performance electronic components.

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 531-91-9 N,N'-diphenyl-p-phenylenediamine 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 62-53-3 aniline 
• 36809-26-4 4-N,N-diphenylamino-1-bromobenzene 

Downstream Products

• 113664-24-7 N,N,N′,N′-tetrakis(4-bromophenyl)[1,1′-biphenyl]-4,4′-diamine 
• 249920-78-3 4,4'-bis[(p-allylphenyl)phenylamino]biphenyl 
• 640756-41-8 N,N,N',N'-tetrakis-(p-allylphenyl)-biphenyl-4,4'-diamine 
• 1262958-10-0 N,N'-diphenyl-N,N'-bis(4-((E)-2-(triethoxysilyl)-vinyl)phenyl)biphenyl-4,4'-diamine 
• 137911-28-5 4,4′-([1,1′-biphenyl]-4,4′-diylbis(phenylazanediyl))dibenzaldehyde 

Relevant articles and documents

Synthesis of triphenylamine (TPA) dimers and applications in cell imaging

A variety of triphenylamine (TPA) are shown to undergo C–C bond formation using quinone-based chloranil/H+ reagent as the metal free oxidative system to afford triphenylamine dimers very conveniently. Then, TPA dimers have been further converte

Metal-Free Oxidative C-C Coupling of Arylamines Using a Quinone-Based Organic Oxidant

A variety of arylamines are shown to undergo oxidative C-C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal-free) oxidant system to afford benzidines/naphthidines. Arylamines (3°/2°) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C-C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.

Oxidative Dimerization of Triarylamines Promoted by WCl6, Including the Solid State Isolation and the Crystallographic Characterization of a Triphenylammonium Salt

The triphenylammonium salt [NHPh3][WCl6], 1, and the product of the C-C dimerization of triphenylamine, Ph2N(C6H4)2NPh2, 2, were afforded from the reaction between WCl6 and NPh3 in CH2Cl2. Compound 2 was isolated in 43% yield upon hydrolysis of the reaction mixture. The X-ray structure of 1 provides the first crystallographic characterization of the triphenylammonium ion. Combined EPR and DFT studies gave insight into the reaction mechanism, and allowed the identification of WCl5···[Cl(C6H4)NPh2] as a presumable key intermediate. The reactions of WCl6 with 4-bromotriphenylamine, 4,4′-dimethyltriphenylamine, 9-phenylcarbazole, followed by hydrolytic treatment, led to the dimerization products 3-6, in admixture with variable amounts of the parent amines. N,N,N′,N′-tetrakis(4-bromophenyl)-[1,1′-biphenyl]-4,4′-diamine, 3, was isolated in 60% yield from the reaction of WCl6 with 4,4′-dibromotriphenylamine.

Hole injection/transport materials derived from heck and sol-gel chemistry for application in solution-processed organic electronic devices

An organosilicate polymer, based on N,N′-diphenyl-N,N′-bis(4- ((E)-2-(triethoxysilyl)vinyl)phenyl)biphenyl-4,4′-diamine (TEVS-TPD) with extended conjugation between the Si atom and the aromatic amine, was prepared under mild conditions via sequential Heck and sol-gel chemistry and used as an alternative to poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), the most widely used planarizing hole injection/transport layer in solution-processed organic electronic devices. Spin-coating TEVS-TPD polymer solutions yield defect-free, uniform, thin films with excellent adhesion to the ITO electrode. Upon thermal cross-linking at 180 C, the cross-linked polymer exhibits excellent solvent resistance and electrochemical stability. Solution-processed organic light emitting diode (OLED) devices using iridium-based triplet emitting layers and cross-linked TEVS-TPD films as a hole injection/transport layer show significantly improved performance including lower leakage current, lower turn-on voltage, higher luminance, and stability at high current density, as compared to the control device prepared with PEDOT:PSS.

Covalently bound hole-injecting nanostructures. Systematics of molecular architecture, thickness, saturation, and electron-blocking characteristics on organic light-emitting diode luminance, turn-on voltage, and quantum efficiency

Hole transporting materials are widely used in multilayer organic and polymer light-emitting diodes (OLEDs, PLEDs, respectively) and are indispensable if device electroluminescent response and durability are to be truly optimized. This contribution analyz

Organic light-emitting diodes and related hole transport compounds

New organic light-emitting diodes and related hole transport compounds and methods for fabrication, using siloxane self-assembly techniques.

Molecularly "Engineered" Anode Adsorbates for Probing OLED Interfacial Structure-Charge Injection/Luminance Relationships: Large, Structure-Dependent Effects

Molecule-scale structure effects at organic light-emitting diodes (OLED) anode?organic transport layer interfaces are probed via a self-assembly approach. A series of ITO anode-linked silyltriarylamine molecules differing in aryl group and linker density are synthesized for this purpose and used to probe the relationship between nanoscale interfacial chemical structure, charge injection and electroluminescence properties. Dramatic variations in hole injection magnitude and OLED performance can be correlated with the molecular structures and electrochemically derived heterogeneous electron-transfer rates of such triarylamine fragments, placed precisely at the anode?hole transport layer interface. Very bright and efficient (～70000 cd/m2 and ～2.5% forward external quantum efficiency) OLEDs have thereby been fabricated. Copyright