122738-21-0

Basic information

• Product Name: N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE
• Synonyms: N4,N4,N4',N4'-Tetrakis(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine;N,N,N',N'-TETRAKIS(4;MeO-TPD,N4,N4,N4',N4'-Tetrakis(4-Methoxyphenyl)-[1,1'-biphenyl]-;N,N,Nμ,Nμ-Tetrakis(4-Methoxyphenyl)benzidine;N,N,N',N'-Tetrakis(4-methoxyphenyl)benzidine 98%;N′N,N,N′-Tetrakis(4-methoxyphenyl)benzidine
• CAS NO: 122738-21-0
• Molecular Formula: C₄₀H₃₆N₂O₄
• Molecular Weight: 608.72
• Mol File: 122738-21-0.mol

Chemical Properties

• Melting Point: 190.0 to 194.0 °C
• Boiling Point: 752.5 °C at 760 mmHg
• Flash Point: 188.6 °C
• Appearance: /
• Density: 1.186
• Storage Temp.: 2-8°C
• PKA: -1.27±0.60(Predicted)
• CAS DataBase Reference: N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE(122738-21-0)
• EPA Substance Registry System: N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE(122738-21-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 122738-21-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Photovoltaic (OPV) Devices:
N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE is used as a hole transport material for OPV devices to improve their overall performance and efficiency. Its air stability and ability to enhance mobility make it a popular choice in this application.
Used in Organic Light-Emitting Diode (OLED) Devices:
In the OLED industry, N,N,N',N'-TETRAKIS(4-METHOXYPHENYL)-1,1'-BIPHENYL-4,4'-DIAMINE is used to increase the brightness of the devices, with reported improvements of up to 14300 cd/m2 at 13V. This enhancement in brightness is crucial for the development of high-quality display technologies and energy-efficient lighting solutions.

Upstream product

• 696-62-8 para-iodoanisole 
• 92-87-5 p,p'-diaminobiphenyl 
• 20440-94-2 N,N-bis(4-methoxyphenyl)aniline 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 101-70-2 bis(4-methoxyphenyl)amine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 623-12-1 4-chloromethoxybenzene 
• 75752-15-7 4,4'-diaminobiphenyl hydrochloride 

Downstream Products

• 1357929-94-2 C₅₆H₈₄N₂O₈Si₈ 
• 1357929-96-4 C₆₄H₁₀₈N₂O₁₂Si₁₂ 
• 211125-43-8 N,N,N',N',-tetra(4-hydroxyphenyl)-[1,1'-biphenyl]-4,4'-diamine 

Relevant articles and documents

Ullmann reaction in tetraethyl orthosilicate: A novel synthesis of triarylamines and diaryl ethers

A novel synthesis of triarylamines and diaryl ethers is reported; a feature of this process is the ligand-free copper-catalysed C-N and C-O bond formation in tetraethyl orthosilicate. The Royal Society of Chemistry.

A novel panchromatic shutter based on an ambipolar electrochromic system without supporting electrolyte

Two triphenylamine derivatives, N,N,N′,N′-tetrakis(4-methoxyphenyl)-1,4-phenylenediamine TPPA and N,N,N′,N′-tetrakis(4-methoxyphenyl)-1,1′-biphenyl-4,4′-diamine TPB, were successfully prepared and combined with HV to fabricate the electrochromic device as a panchromatic shutter for the application of transparent display. The obtained electrochromic device exhibits exceptional novel electrochromic properties, including enhanced color contrast, switching time, and long-term stability. Furthermore, it is worth mentioning that the most important contribution of this ambipolar system approach is that no supporting electrolyte is added into the device.

PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides

Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.

General design of self-doped small molecules as efficient hole extraction materials for polymer solar cells

The development of high performance hole transport materials (HTMs) without a chemical dopant is critical to achieve long-term device durability. The general design of self-doping materials based on a phenolamine structure with strong electronic spin conc

Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes

A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.

Effects of solvent and base on the palladium-catalyzed amination: PdCl 2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides

A readily accessible catalytic system, PdCl2(Ph 3P)2/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′- diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4′-diaminobiphenyls and aryl bromides.

Liquid triarylamines: The scope and limitations of piers-rubinsztajn conditions for obtaining triarylamine-siloxane hybrid materials

New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

Cu(II)-mediated generation of triarylamine radical cations and their dimerization. An easy route to tetraarylbenzidines

(Chemical Equation Presented) Triphenylamine (TPA) derivatives react with Cu2+ in acetonitrile to give TPA radical cations which undergo dimerization and deprotonation reactions to yield tetraphenylbenzidines (TPB). Synthetic utility of this reaction is demonstrated using several triphenylamine derivatives, and yields in excess of 80% are obtained in most cases. Involvement of the amine radical cations in these reactions was confirmed by ESR and absorption spectroscopic studies. A mechanism consistent with all observations is proposed. This study also revealed a very good correlation between the free energy change for radical cation formation and product yields.