N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine

Base Information

• Chemical Name: N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine
• CAS No.: 123847-85-8
• Molecular Formula: C₄₄H₃₂N₂
• Molecular Weight: 588.751
• Hs Code.: 29215900
• DSSTox Substance ID: DTXSID20408009
• Nikkaji Number: J889.767K
• Wikidata: Q72446555
• Mol file: 123847-85-8.mol

Synonyms:123847-85-8;N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine;alpha-NPB;N,N'-Bis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine;4,4'-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl;N-[4-[4-(N-naphthalen-1-ylanilino)phenyl]phenyl]-N-phenylnaphthalen-1-amine;n,n'-bis(naphthalen-1-yl)-n,n'-bis(phenyl)-benzidine;N,N'-Bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine;N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine;N,N'-Di-1-naphthyl-N,N'-diphenylbenzidine;N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine;N,N'-Bis(1-naphthalenyl)-N,N'-bisphenyl-(1,1'-biphenyl)-4,4'-diamine;MFCD03093246;[1,1'-Biphenyl]-4,4'-diamine, N,N'-di-1-naphthalenyl-N,N'-diphenyl-;N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine;alpha-Npd;C44H32N2;N,N'-Di[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-diamine;N,N'-di-[(1-naphthalenyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-diamine;n,n'-bis(1-naphthyl)-n,n'-diphenyl-1,1'-biphenyl-4,4'-diamine;SCHEMBL23047;YSWG757;DTXSID20408009;IBHBKWKFFTZAHE-UHFFFAOYSA-N;BCP20455;AKOS005145695;N,N'-Biphenyl-N,N'-bis-(1-naphthenyl)-[1,1'-biphenyl]-4,4'-diamine;CS-W011438;NPD, 98.0%;SB66492;N,N'-diphenyl-N,N'-dinaphthylbenzidine;AC-33685;AS-11137;SY039183;D3970;D5126;FT-0652598;2-Amino-5-methoxy-4,6(1H,5H)-pyrimidinedione;4,4-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl;N,N/'-Di(1-naphthyl)-N,N/'-diphenylbenzidine;A805159;n,n'-di(naphthalene-1-yl)-n,n'-diphenylbenzidine;n,n'-di(naphthalene-1-yl)-n,n'-diphenyl-benzidine;N,N'-di(l-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl;N4,N4'-Di(1-naphthyl)-N4,N4'-diphenylbiphenyl-4,4'-diamine;N,N'-Di-1-naphthyl-N,N'-diphenylbenzidine (purified by sublimation);N4,N4'-di(naphthalen-1-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine;N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine, 96%;N,N'-Di[(1-naphthalenyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-dimine;N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine, sublimed grade, 99%;N~4~,N~4'~-Di(naphthalen-1-yl)-N~4~,N~4'~-diphenyl[1,1'-biphenyl]-4,4'-diamine;N4,N4\'-Di(naphthalen-1-yl)-N4,N4\'-diphenyl-[1,1\'-biphenyl]-4,4\'-diamine;N,N-di-[(1-naphthalenyl)-N,N-diphenyl]-1,1-biphenyl)-4,4-diamine;N-[4-[4-[N-(1-naphthyl)anilino]phenyl]phenyl]-N-phenyl-naphthalen-1-amine;N4,N4 inverted exclamation mark -Di(1-naphthyl)-N4,N4 inverted exclamation mark -diphenylbiphenyl-4,4 inverted exclamation mark -diamine

Chemical Property of N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine

Chemical Property:

• Appearance/Colour: electronic;pharmacetical;Light yellow powder
• Melting Point: 279-283 °C
• Boiling Point: 772.5 °C at 760 mmHg
• PKA: -0.08±0.50(Predicted)
• Flash Point: 340.8 °C
• PSA: 6.48000
• Density: 1.213 g/cm³
• LogP: 12.59960
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Heated), DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly
• XLogP3: 12.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 588.256549029
• Heavy Atom Count: 46
• Complexity: 829

Purity/Quality:

99% ^*data from raw suppliers

N,N''-Di-(1-naphthyl)-N,N''-diphenyl-(1,1''-biphenyl)-4,4''-diamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N(C2=CC=C(C=C2)C3=CC=C(C=C3)N(C4=CC=CC=C4)C5=CC=CC6=CC=CC=C65)C7=CC=CC8=CC=CC=C87
• Description: N,N′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine, also known as NPB or NPD, has been used intensively in OLEDs and other organic electronic devices such as polymer photovoltaics (OPV) and perovskite solar cells for its outstanding hole transport capability.
• Uses: Hole transporting material for OLED devices

Technology Process of N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine

There total 11 articles about N4,N4'-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

{4-[(naphthalen-1-yl)(phenyl)amino]phenyl}boronic acid (717888-41-0) + N-(4-bromophenyl)-N-phenyl-1-naphthylamine (138310-84-6) → 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (123847-85-8)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; In water; toluene; at 85 ℃; for 24h; Inert atmosphere;

Reference yield: 95.0%

1-Bromonaphthalene (90-11-9) + N,N'-diphenyl-p-phenylenediamine (531-91-9) → 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (123847-85-8)

Guidance literature:

With sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 20 - 130 ℃; Inert atmosphere;

Reference yield: 93.0%

4-(4-bromophenyl)bromobenzene (92-86-4) + N-phenyl-1-naphthylamine (90-30-2) → 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (123847-85-8)

Guidance literature:

N-phenyl-1-naphthylamine; With n-butyllithium;

4-(4-bromophenyl)bromobenzene; With bis[tris(2-methylphenyl)phosphine]palladium; In toluene; at 100 ℃;

DOI:10.1002/jccs.200100155

upstream raw materials:

4-(4-bromophenyl)bromobenzene

N-phenyl-1-naphthylamine

1-Bromonaphthalene

N,N'-diphenyl-p-phenylenediamine

Downstream raw materials:

N-(1-Naphthyl)-N,N'-diphenylbenzidine

N,N'-di(1-naphthyl)-N-phenyl-N'-(4-(hydroxymethyl)phenyl)benzidine

C₇₁H₅₀F₆N₂O₆

C₄₅H₃₂N₂O

Refernces

Anodic oxidation of novel hole-transporting materials derived from tetraarylbenzidines. Electrochemical and spectroscopic characterization

10.1135/cccc20001403

The purpose of the study was to prepare fluorenylidene-linked triarylamines using the palladium-catalyzed Hartwig–Buchwald amination and investigate their redox and spectral properties. The researchers synthesized compounds 4 and 5, which contain two hole-transporting units linked by a non-conjugated fluorene bridge, aiming to improve the thermal and film-forming properties of OLED materials while preserving their electronic characteristics. The study concluded that these linked triarylamines showed significantly increased glass-transition temperatures compared to low-molecular-weight analogues conventionally used in OLEDs, with their desirable electronic properties intact. The research involved the use of various chemicals, including N,N,N′,N′-tetraphenylbenzidine (TPB), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (α-NPD), triphenylamine (TPA), and tetraarylbenzidine derivatives, as well as palladium catalysts and other reagents necessary for the Hartwig–Buchwald amination process.