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4,4',4''-Triacetyltriphenylamine, a chemical compound with the molecular formula C30H23NO3, is a derivative of triphenylamine, which is a well-known electron donor in the realm of organic electronics. 4,4',4''-TRIACETYLTRIPHENYLAMINE is characterized by its high thermal stability and robust electron-donating properties, making it a valuable material for the advancement of efficient and stable organic electronic devices.

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  • 4181-21-9 Structure
  • Basic information

    1. Product Name: 4,4',4''-TRIACETYLTRIPHENYLAMINE
    2. Synonyms: 4,4',4''-TRIACETYLTRIPHENYLAMINE
    3. CAS NO:4181-21-9
    4. Molecular Formula: C24H21NO3
    5. Molecular Weight: 371.43
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 4181-21-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 561.3±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.178±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: -9.34±0.50(Predicted)
    10. CAS DataBase Reference: 4,4',4''-TRIACETYLTRIPHENYLAMINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4,4',4''-TRIACETYLTRIPHENYLAMINE(4181-21-9)
    12. EPA Substance Registry System: 4,4',4''-TRIACETYLTRIPHENYLAMINE(4181-21-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4181-21-9(Hazardous Substances Data)

4181-21-9 Usage

Uses

Used in Organic Electronics Industry:
4,4',4''-Triacetyltriphenylamine is utilized as a hole-transporting material for its ability to facilitate the movement of positive charge carriers, which is crucial in the performance of organic light-emitting diodes (OLEDs). Its role in enhancing the efficiency and stability of these devices is significant, contributing to brighter and longer-lasting displays and lighting solutions.
Used in Organic Photovoltaics (OPVs):
In the field of organic photovoltaics, 4,4',4''-Triacetyltriphenylamine serves a similar function, improving the transport of holes within the solar cells. This contributes to the overall efficiency of the OPVs, making them more effective at converting sunlight into electricity.
Used in Organic Field-Effect Transistors (OFETs):
4,4',4''-Triacetyltriphenylamine also finds application in the development of organic field-effect transistors, where its electron-donating characteristics are leveraged to improve the performance of these transistors, potentially leading to advances in flexible and low-cost electronic devices.
Used in Organic Semiconductor Materials:
4,4',4''-TRIACETYLTRIPHENYLAMINE is further explored for its potential in the creation of organic semiconductor materials, where its unique properties can be harnessed to develop new materials with tailored electronic properties for various applications in the organic electronics domain.

Check Digit Verification of cas no

The CAS Registry Mumber 4181-21-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,8 and 1 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4181-21:
(6*4)+(5*1)+(4*8)+(3*1)+(2*2)+(1*1)=69
69 % 10 = 9
So 4181-21-9 is a valid CAS Registry Number.

4181-21-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1',1''-(nitrilotris(benzene-4,1-diyl))triethanone

1.2 Other means of identification

Product number -
Other names Tris-[4-acetyl-phenyl]-amin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4181-21-9 SDS

4181-21-9Relevant articles and documents

A highly luminescent chiral tetrahedral Eu4L4(L′)4 cage: Chirality induction, chirality memory, and circularly polarized luminescence

Zhou, Yanyan,Li, Hongfeng,Zhu, Tianyu,Gao, Ting,Yan, Pengfei

, p. 19634 - 19643 (2019)

Chiral lanthanide cages with circularly polarized luminescence (CPL) properties have found potential application in enantioselective guest recognition and sensing. However, it still remains a big challenge to develop a simple and robust method for the dia

Homochiral crystallization of metal-organic silver frameworks: Asymmetric [3+2] cycloaddition of an azomethine ylide

Jing, Xu,He, Cheng,Dong, Dapeng,Yang, Linlin,Duan, Chunying

, p. 10127 - 10131,5 (2012)

Enantiomeric silver-based MOFs were obtained through a homochiral crystallization of cinchonine and cinchonidine enantiomers as chiral adducts with silver. These MOFs exhibited excellent catalytic activity for asymmetric [3+2] cycloaddition (see scheme),

Multi-Component Metal-Organic Frameworks Significantly Boost Visible-Light-Driven Hydrogen Production Coupled with Selective Organic Oxidation

Duan, Chunying,He, Cheng,Jing, Xu,Li, Hanning,Yang, Yang

supporting information, p. 1237 - 1244 (2021/04/09)

Visible-light-driven hydrogen production coupled with selective organic oxidation has attracted increasing attention, as it not only provides clean and renewable energy, but also utilizes the other half reaction to achieve some value-added organic chemicals. Metal-organic frameworks based on metal clusters and organic ligands self-assembly give a perspective on the formation of multifunctional heterogeneous photocatalyst to significantly boost visible-light photocatalytic activities under mild conditions. By incorporating two types of photoactive units, tricarboxytriphenylamine (H3TCA) and tris(4-(pyridinyl)phenyl)amine (NPy3), into a single metal-organic frameworks, a multi-component MOF Co-MIX was obtained. With the redox active metal centers enabling the photoexcitation reduction of protons into hydrogen and the photogenerated holes promoting considerable oxidation of substrates, the resulting Co-MIX exhibits high catalytic activity for the photocatalytic hydrogen production coupled with selective oxidation of benzylamine or 1,2,3,4-tetrahydroisoquinoline. Importantly, the photocatalytic experiments of single-component Co-TCA and Co-NPy3 verified the positive synergistic effects on stability and photocatalytic ability of the two ligands (H3TCA and NPy3) in one single MOF, revealing that the multi-component strategy is very important for the efficient charge separation and excellent photocatalytic activity of the catalyst.

A cerium-based MOFzyme with multi-enzyme-like activity for the disruption and inhibition of fungal recolonization

Abdelhamid, Hani Nasser,Mahmoud, Ghada Abd-Elmonsef,Sharmouk, Walid

, p. 7548 - 7556 (2020/09/18)

A cerium-based metal-organic framework (Ce-MOF, denoted as AU-1) was synthesized using a solvothermal method by employing 4,4′,4′′-nitrilotribenzoic acid (H3NTB) as the linker and cerium clusters as the metal center. The material was considered as a MOFzy

Cadmium-based metal-organic framework material as well as preparation method and application thereof

-

Paragraph 0039; 0040, (2019/02/25)

The invention discloses a cadmium-based metal-organic framework material as well as a preparation method and application thereof. Metal ions Cd are used as nodes, 4,4',4''-tricarboxytriphenylamineis used as an organic linking main ligand, 4,4'-azopyri

2-carbonyl-5-aryl-1, 3, 4- -oxadiazole sterically hindered luminescent material and preparation method thereof

-

Paragraph 0053-0054, (2019/01/16)

The invention provides a 2-carbonyl-5-aryl-1, 3, 4- -oxadiazole sterically hindered luminescent material and a preparation method thereof. The material is characterized in that 5-aryl-1, 3, 4- -oxadiazole and spiro-arene or azacyclo are connected through

Novel metal-organic framework with tunable fluorescence property: Supramolecular signaling platform for polynitrophenolics

Venkateswarulu,Pramanik, Avijit,Koner, Rik Rani

supporting information, p. 6348 - 6352 (2015/04/14)

With the aid of a rotational C3-symmetric tricarboxytriphenylamine based ligand, a new Cd-MOF was synthesized and characterized by various spectroscopic techniques as well as by single-crystal X-ray diffraction analysis. The structural investig

Molecular design for the highly-sensitive piezochromic fluorophores with tri-armed framework containing triphenyl-quinoline moiety

Hsiao, Tai-Shen,Chen, Tai-Lin,Chien, Wei-Lun,Hong, Jin-Long

, p. 161 - 167 (2014/01/17)

Two tri-armed piezochromic fluorescent molecules of tris(4-(4- phenylquinolin-2-yl)phenyl)amine (TPA-3Qu) and tris(4-(6-(9H-carbazol-9-yl)-4- phenylquinolin-2-yl)phenyl)amine (TPA-3QuCz) were prepared and found to exhibit keen fluorescence responses towar

Bipolar luminescent materials containing pyrimidine terminals: Synthesis, photophysical properties and a theoretical study

Weng, Jiena,Mei, Qunbo,Fan, Quli,Ling, Qidan,Tong, Bihai,Huang, Wei

, p. 21877 - 21887 (2013/11/06)

A new series of 4-monosubstituted pyrimidine bipolar materials containing a carbazole (PM1-PM2) or a triphenylamine (PM3-PM5) moiety as the electron donor have been synthesized by a ZnCl2-catalyzed three-component coupling reaction. These 4-monosubstituted pyrimidine compounds were characterized by UV-vis and fluorescence spectroscopy, cyclic voltammetry, as well as density functional theory (DFT) calculations. It was intriguing to find that these 4-monosubstituted pyrimidine compounds exhibited bright fluorescence with excellent quantum yields (~0.53-0.93) in the blue region. PM1 and PM2 had a lower LUMO than that of CBP (4,4-di(9H-carbazol-9-yl)biphenyl), meaning that both of them had better electron injection and transfer abilities. The variation tendencies of energy levels and absorption spectra obtained from DFT calculations agreed well with those from experiment. Other electronic properties including ionization potentials (IP), electronic affinities (EA), and reorganization energies (λhole and λ electron) have been theoretically studied as well. These electronic properties could be tuned by introducing a different number of pyrimdin-4-yl moieties onto to the donor fragments. The incorporation of pyrimdin-4-yl can significantly decrease the λelectron and then improve the electron-accepting and hole-electron charge balance abilities. The combined theoretical and experimental studies offer insights into the nature of bipolar molecules containing 4-monosubstituted pyrimidine moieties, and provided a fertile ground for the design of appropriate ambipolar materials for optoelectronic applications. The Royal Society of Chemistry 2013.

Blue-light-emitting multifunctional triphenylamine-centered starburst quinolines: Synthesis, electrochemical and photophysical properties

Jiang, Peng,Zhao, Dong-Dong,Yang, Xiao-Li,Zhu, Xiao-Lin,Chang, Jin,Zhu, Hong-Jun

scheme or table, p. 4704 - 4711 (2012/08/08)

A series of triphenylamine-centered starburst quinolines (1a-1g) have been synthesized by Friedlaender condensation of the 4,4′,4′′- triacetyltriphenylamine (2) and 2-aminophenyl ketones (3a-3g) in the presence of catalytic sulfuric acid and characterized well. They are thermally robust with high glass transition temperatures (above 176.4 °C) and decomposition temperatures (above 406 °C). These compounds emit blue fluorescence with λEmmax ranging from 433 to 446 nm in dilute toluene solution and 461 to 502 nm in the solid-state and have a relatively high efficiency (Φu = 0.98-0.57). 1a-1g have estimated ionization potentials (IP) of 4.54 to 6.45 eV which are significantly near or higher than those of well-known electron transport materials (ETMs), including tris(8- hydroxyquinoline)aluminium (Alq3) (IP = 5.7-5.9 eV), and previously reported oligoquinolines (IP = 5.53-5.81 eV). Quantum chemical calculations using DFT B3LYP/6-31G* showed the highest occupied molecular orbital (HOMO) of -5.05 to -4.81 eV, which is close to the work function of indium tin oxide (ITO). These results demonstrate the potential of 1a-1g as hole-transporting/light-emitting/electron-transport materials and the host-materials of a dopant for hole-injecting for applications in organic light-emitting devices.

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