29261-33-4

Basic information

• Product Name: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane
• Synonyms: TCNQF4;TETRAFLUOROTETRACYANOQUINODIMETHANE;2,3,5,6-Tetrafluoro-7,7,8,8-Te;(2,3,5,6-tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile;tcnqf4 (organic electronic material);2,3,5,6-Tetrafluorotetracyanoquinodimethane 95%;2,3,5,6-Tetrafluorotetracyanoquinodimethane95%;2,3,5,6-TETRAFLUORO-7,7,8,8-TETRACYANOQUINODIMETHANE SUBLIMED [ORGANIC ELECTRONIC MATERIAL] 99%
• CAS NO: 29261-33-4
• Molecular Formula: C₁₂F₄N₄
• Molecular Weight: 276.15
• Product Categories: pharmacetical;Electronic Chemicals;Acceptors (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;Highly Purified Reagents;Other Categories;Refined Products by Sublimation;TCNQ Derivatives;oled materials
• Mol File: 29261-33-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 285-290 °C(lit.)
• Boiling Point: -89.6±40.0 °C(Predicted)
• Appearance: yellow-greenish or orange-brown powder
• Density: 1.7075 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 2157887
• CAS DataBase Reference: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane(29261-33-4)
• EPA Substance Registry System: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane(29261-33-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 36/37/38-20/21/22-23/24/25
• Safety Statements: 22-24/25-36/37/39-26-36/37
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 29261-33-4(Hazardous Substances Data)

Usage

Classification

Fluorinated compounds, p-type dopant, Strong electron acceptor, Hole-injection materials, Hole-transport layer material, OLEDs, Polymer Solar Cells, Perovskite Solar Cells, OFETs.

Applications

F4TCNQ is one of the most widely used and most effective p-type dopants due to its strong electron-accepting ability and the extended π system. It has a deep LUMO level (-5.2 eV) which is energetically in the vicinity of the HOMO level of many organic semiconductors. Doping is facilitated by charge transfer from the HOMO level of the host to the LUMO of the dopant molecule. Pin devices with F4TCNQ doped 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) serving as the p-doped HTL show high luminance and efficiency at extremely low operating voltages: For instance, a luminance of 1000 cd/m2 is reached at a voltage of 2.9 V. It has been reported that by controlling the doping concentration, the PCE of the PCDTBT:F4TCNQ solar cells increased from 6.41% to 7.94%, mainly due to improving the photocurrent with a F4TCNQ weight ratio of the blend lower than 0.5% [2]. F4TCNQ is also used as the p-type dopant for graphenes.

Description

F4TCNQ is?one of the most widely used and most effective p-type dopants due to its strong electron-accepting ability and the extended?π?system. It has a deep LUMO level (-5.2 eV) which is energetically in the vicinity of the?HOMO level of many organic semiconductors. Doping is facilitated by charge transfer from the HOMO level of the host to the LUMO of the dopant molecule.?Pin devices with F4TCNQ doped 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) serving as the p-doped HTL show high luminance and efficiency at extremely low operating voltages: For instance, a luminance of 1000 cd/m2 is?reached at a voltage of 2.9 V .

Chemical Properties

Yellow-greenish or orange-brown powder

Uses

F4-TCNQ is the p-type dopant for hole-only devices and field effect transistors with organic hole transport layers (HTL). It is used in the preparation of a bilayer structure of F4-TCNQ and pentacene to study improved thermoelectric performance of organic thin films.

General Description

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) is a dopant used in the fabrication of organic semiconductors. It can tune the electronic properties as its lowest unoccupied molecular orbital is at a desirable energy level required to oxidize a wide range of semiconductors.

Upstream product

• 392-56-3 Hexafluorobenzene 
• 15041-74-4 2,3,5,6-tetrafluorobenzene-1,4-dicarbonyl dichloride 
• 652-36-8 2,3,5,6-tetrafluoroterephthalic acid 
• 970-16-1 4-hydroxy-2,3,5,6-tetrafluoro-4'-dimethylaminoazobenzene 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 527-21-9 2,3,5,6-tetrafluoro-1,4-benzoquinone 
• 109-77-3 malononitrile 
• 29097-86-7 2,3,5,6-Tetrafluor-1,4-bis(tert.-butyldicyanomethyl)benzol 

Downstream Products

• 121192-67-4 octamethylferrocenium(III) perfluoro-7,7,8,8-tetracyano-p-quinodimehane radical anion 
• 244218-37-9 [Fe((η(5)-C5(CH3)4S)2S)](((CN)2C)2C6F4) 
• 244218-35-7 [Fe(η(5)-C5(CH3)4SCH3)2](((CN)2C)2C6F4) 

Relevant articles and documents

Synthesis method of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane

The invention discloses a synthesis method of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane and relates to the technical field of organic electroluminescent materials. On the basis of simplifying the synthesis method, wastewater generated by post-treatment is reduced, and the safety of a synthesis process is improved, so that the synthesis method is applicable to industrial production. The synthesis method comprises the following steps: firstly, carrying out a condensation reaction by taking 2,3,5,6-tetrafluoroterephthaloyl chloride andtrialkylsilyl cyanide as raw materials under an oxygen-free and dry environment to obtain an intermediate; and then, removing trialkylsiloxy in the intermediate to obtain F4-TCNQ. The synthesis method of the 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, disclosed by the invention, is used for synthesizing organic electroluminescent materials.

Nanostructured charge transfer complex of CuTCNQF4 for efficient photo-removal of hexavalent chromium

The high toxicity of hexavalent chromium warrants the development of efficient catalysts that could reduce chromium into relatively non-toxic trivalent chromium species. Pristine charge transfer complexes of the MTCNQ family (M = Cu or Ag; TCNQ = 7,7,8,8-