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Triphenylamine

Base Information Edit
  • Chemical Name:Triphenylamine
  • CAS No.:603-34-9
  • Deprecated CAS:149006-34-8
  • Molecular Formula:C18H15N
  • Molecular Weight:245.324
  • Hs Code.:29214980
  • European Community (EC) Number:210-035-5
  • ICSC Number:1366
  • NSC Number:66458
  • UNII:NJS65M2DS2
  • DSSTox Substance ID:DTXSID4022076
  • Nikkaji Number:J54.231H
  • Wikipedia:Triphenylamine
  • Wikidata:Q7843272
  • ChEMBL ID:CHEMBL3819197
  • Mol file:603-34-9.mol
Triphenylamine

Synonyms:TRIPHENYLAMINE;603-34-9;N,N-Diphenylaniline;Benzenamine, N,N-diphenyl-;Triphenyl amine;N,N-Diphenylbenzenamine;Amine, triphenyl;CCRIS 4887;HSDB 2098;EINECS 210-035-5;NSC 66458;UNII-NJS65M2DS2;NJS65M2DS2;AI3-17278;MFCD00003020;NSC-66458;N,N,N-Triphenylamine;N,N-Diphenylbenzeneamine;diphenylaniline;Trifenilamina;Trifenylamin;Trisphenylamine;4-diphenylaminobenzene;880462-20-4;Triphenylamine, 98%;Benzenamine,N-diphenyl-;N,N,N-Triphenylamine #;Bencenamina, n, n-difenil-;SCHEMBL30959;BIDD:GT0660;CHEMBL3819197;DTXSID4022076;N,N-diphenylaniline;Triphenylamine;N,N-DIPHENYLANILINE [HSDB];ADAL1012817;NSC66458;AKOS015840682;CS-W012714;LS-1437;SB66357;AC-13457;AS-14885;SY005738;FT-0632501;T0507;EN300-114099;Triphenylamine, Vetec(TM) reagent grade, 98%;A832698;Q7843272;W-105262

Suppliers and Price of Triphenylamine
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Triphenylamine
  • 10g
  • $ 85.00
  • TCI Chemical
  • Triphenylamine >98.0%(GC)
  • 250g
  • $ 160.00
  • TCI Chemical
  • Triphenylamine >98.0%(GC)
  • 25g
  • $ 27.00
  • SynQuest Laboratories
  • Trisphenylamine
  • 100 g
  • $ 144.00
  • SynQuest Laboratories
  • Trisphenylamine
  • 1 kg
  • $ 552.00
  • SynQuest Laboratories
  • Trisphenylamine
  • 500 g
  • $ 328.00
  • Sigma-Aldrich
  • Triphenylamine 98%
  • 100g
  • $ 172.00
  • Sigma-Aldrich
  • Triphenylamine 98%
  • 25g
  • $ 56.90
  • Matrix Scientific
  • Triphenylamine 98%
  • 10g
  • $ 57.00
  • Frontier Specialty Chemicals
  • Triphenylamine 99%
  • 25g
  • $ 60.00
Total 150 raw suppliers
Chemical Property of Triphenylamine Edit
Chemical Property:
  • Appearance/Colour:off-white solid 
  • Vapor Pressure:1.62E-05mmHg at 25°C 
  • Melting Point:124-128 °C(lit.) 
  • Refractive Index:1.3530 (estimate) 
  • Boiling Point:365 °C at 760 mmHg 
  • PKA:-3.04±0.30(Predicted) 
  • Flash Point:157.3 °C 
  • PSA:3.24000 
  • Density:1.112 g/cm3 
  • LogP:5.15640 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:Chloroform (Slightly) 
  • Water Solubility.:insoluble 
  • XLogP3:5.7
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:3
  • Exact Mass:245.120449483
  • Heavy Atom Count:19
  • Complexity:202
Purity/Quality:

99% *data from raw suppliers

Triphenylamine *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/38-36/37/38-38-36 
  • Safety Statements: 26-28-37/39-26,37/39 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Amines, Polyaromatic
  • Canonical SMILES:C1=CC=C(C=C1)N(C2=CC=CC=C2)C3=CC=CC=C3
  • Inhalation Risk:A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
  • Effects of Short Term Exposure:The substance is mildly irritating to the eyes and skin.
  • General Description Triphenylamine (TPA) is a versatile organic compound widely used in optoelectronic applications, particularly in the development of organic light-emitting diodes (OLEDs) and two-photon absorption (2PA) materials. It serves as a core structure in fluorescent emitters and aggregation-induced emission (AIE) luminogens, contributing to deep-blue emission, high efficiency, and reduced efficiency roll-off in OLEDs. TPA derivatives exhibit strong electron-donating properties, enabling intramolecular charge transfer (ICT) and solvatochromic effects, which are crucial for tuning photophysical properties. Additionally, TPA-based compounds demonstrate excellent thermal stability, high quantum yields, and large two-photon absorption cross-sections, making them suitable for applications in nonlinear optics and biomolecule labeling. The substituents on TPA significantly influence intermolecular interactions, affecting luminescence and device performance in OLEDs.
Technology Process of Triphenylamine

There total 146 articles about Triphenylamine 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:
Guidance literature:
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 20 ℃; for 1h;
DOI:10.1021/jo025732j
Guidance literature:
With palladium diacetate; sodium t-butanolate; ruphos; In neat (no solvent); at 110 ℃; for 12h; Green chemistry;
DOI:10.1002/ejoc.201402077
Guidance literature:
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate; In neat (no solvent); at 110 ℃; for 12h; Reagent/catalyst; Inert atmosphere; Green chemistry;
DOI:10.1002/ejoc.201501616
Refernces Edit

Structure-simplified and highly efficient deep blue organic light-emitting diodes with reduced efficiency roll-off at extremely high luminance

10.1039/c6cc08501f

The research focuses on the development of structure-simplified, highly efficient deep blue organic light-emitting diodes (OLEDs) that exhibit reduced efficiency roll-off at extremely high luminance. The study involves the synthesis of new fluorescent emitters, NI-1-DPhTPA, NI-2-DPhTPA, BIDPhTPA, and PhIDPhTPA, based on a triphenylamine (TPA) core with electron-poor imidazole derivative groups. These emitters were characterized using 1H, 13C NMR spectrometry, mass spectrometry, and density functional theory (DFT) calculations to evaluate their molecular orbitals and energy band gaps. The thermal stability was assessed through differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), while cyclic voltammograms (CV) were used to estimate HOMO levels. The photophysical properties, including absorption and photoluminescence (PL) spectra, were studied in various solvents to understand solvatochromic shifts and intramolecular charge transfer (ICT) characteristics. The electroluminescent properties of these materials were probed by fabricating non-doped multilayer OLEDs and simplified single-layer OLEDs, with the devices' performance evaluated through current density-voltage-luminance (J-V-L), external quantum efficiency (EQE), and power efficiency (PE) measurements. The research demonstrated record-breaking EQEs exceeding 5.10% at 10,000 cd m-2 for the multilayer devices and an unprecedented 4.22% EQE at 10,000 cd m-2 for the simplified single-layer devices, showcasing the potential for cost-effective, high-luminosity OLED applications.

A new approach to prepare efficient blue AIE emitters for undoped OLEDs

10.1002/chem.201303522

The research focuses on the development of new aggregation-induced emission (AIE) active luminogens, specifically targeting the synthesis of efficient blue AIE emitters for undoped organic light-emitting diodes (OLEDs). The purpose of this study was to address the challenges associated with blue OLEDs, which often suffer from inferior performance due to the large band gap in blue luminogens. The researchers successfully synthesized two deep-blue fluorophores, TPE–pTPA and TPE–mTPA, along with six other compounds for comparison. These luminogens were designed to restrict the π-conjugation length, ensuring blue emission, by incorporating hole-dominated triphenylamine (TPA) and fluorene groups with high luminous efficiency, connected through unconjugated linkages. The study concluded that TPE–pTPA and TPE–mTPA exhibited the best electroluminescence performance with low turn-on voltages and high efficiencies, demonstrating that it is possible to enhance the OLED performance without sacrificing deep-blue emission through rational molecular design. Key chemicals used in the synthesis process included tetraphenylethene (TPE), triphenylamine (TPA), fluorene, and various other aromatic compounds. The researchers also utilized palladium-catalyzed Suzuki coupling reactions for the final product formation, with yields ranging from 60.4 to 85.9%. The compounds were purified and characterized using column chromatography and spectroscopic techniques.

Synthetic strategies to derivatizable triphenylamines displaying high two-photon absorption

10.1021/jo702002y

The study explores the development of highly fluorescent π-conjugated triphenylamines (TPAs) designed for large two-photon absorption (2PA) and biomolecule labeling. The researchers synthesized a set of TPA derivatives with functional linkers at various positions on one phenyl ring, allowing for the introduction of electron-withdrawing groups and chemical functions suitable for biomolecule conjugation. Key chemicals involved include trisformylated or trisiodinated intermediates, which enable the attachment of various electron-withdrawing groups and functional linkers. The monoderivatized three-branched compounds, particularly the benzothiazole (TP-3Bz) series, exhibit remarkable linear and nonlinear optical properties, such as high extinction coefficients, high quantum yields, and high 2-photon cross sections. The study also highlights that the presence of functional side chains does not disturb the two-photon absorption, and monoderivatized two-branched derivatives are also promising candidates for biomolecule labeling. The synthesized compounds' small size, good optical properties, and compatibility with bioconjugation protocols suggest they could be a new class of labels for tracking biomolecules using two-photon scanning microscopy.

Synthesis and characterization of highly soluble two-photon-absorbing chromophores with multi-branched and dendritic architectures

10.1002/ejoc.201001165

The research focuses on the synthesis and characterization of highly soluble, multi-polar fluorene-based chromophores with multi-branched and dendritic architectures. These compounds were designed to exhibit strong two-photon absorption (2PA) properties, which were investigated in both femtosecond and nanosecond time domains. The study explores the relationship between the molecular structure, specifically the number of peripheral electron-donating groups and the size of the π-domain, with the two-photon activities of the model compounds. The experiments involved synthesizing four fluorene-based derivatives with systematic alterations in their molecular structure, which were then subjected to linear and nonlinear optical property measurements. These measurements included one-photon absorption (1PA) and fluorescence spectra, two-photon-excited fluorescence (2PEF) emission properties, and degenerate two-photon absorption spectra measurements. The reactants used in the synthesis included various fluorene and triphenylamine derivatives, along with catalysts and solvents. The analyses used techniques such as NMR, HRMS, and MALDI-TOF MS to characterize the synthesized compounds. The study demonstrated that the model compounds possess large nonlinear attenuation under nanosecond laser pulse irradiation, indicating potential applications as broadband and rapid-responsive optical limiters.

Effect of intermolecular interaction on the characteristics of organic light emitting diodes with TPBB derivatives

10.1080/15421401003608337

The study investigates the effects of intermolecular interactions on the characteristics of organic light emitting diodes (OLEDs) using four synthesized triphenylamine derivatives: 1,3,5-tris(4'-(100-phenyl-benzimidazol-200-yl)phenyl)amine (TPBB), MeO-TPBB, Br-TPBB, and Bu-TPBB. These derivatives were used as emitting layers in OLEDs with a multilayer structure [ITO=NPB (50 nm)=EML (30 nm)=TPBI (20 nm)=Alq3 (10 nm)=LiF (1 nm)=Al]. The research found that the substituents (methoxy, bromine, and n-butyl) significantly influenced the molecular mobility and intermolecular interactions of the TPBB derivatives, leading to different photoluminescence (PL) and electroluminescence (EL) characteristics. The unsubstituted TPBB showed better EL performance, while the substituted derivatives exhibited redshifted spectra and lower luminance and efficiency due to increased intermolecular interactions. The Br-TPBB derivative also experienced a significant decrease in performance due to the heavy atom effect of bromine.

Reversible solid-state mechanochromic luminescence originated from aggregation-induced enhanced emission-active Donor?Acceptor cruciform luminophores containing triphenylamine

10.1016/j.dyepig.2019.107689

This study investigates the design, synthesis, and properties of two torsional donor-acceptor cross-shaped luminophores, FB-CTPAEB and DFB-CTPAEB. These compounds exhibit unique intramolecular charge transfer (ICT) and solid-state fluorescence behaviors, and have high solid-state luminescence efficiencies (up to 0.693 and 0.442, respectively). 4,4''-Bis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3a), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2a via Suzuki-Miyaura coupling reaction, is an intermediate for the synthesis of FB-CTPAEB. 3,3'',5,5''-Tetrakis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3b), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2b via Suzuki-Miyaura coupling, is an intermediate compound used in the synthesis of DFB-CTPAEB. 2-(4-(Diphenylamino)phenyl)acetonitrile is used as the donor moiety in the Knoevenagel condensation reaction to form the final cruciform luminophore. 2,5-Dibromoterephthalaldehyde is the starting material for the synthesis of cruciform luminophores.

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