2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Base Information

• Chemical Name: 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane
• CAS No.: 29261-33-4
• Molecular Formula: C12F4N4
• Molecular Weight: 276.152
• Hs Code.: 29269090
• European Community (EC) Number: 624-300-1
• DSSTox Substance ID: DTXSID10369837
• Nikkaji Number: J209.026K
• Wikidata: Q72505259
• Mol file: 29261-33-4.mol

Synonyms:29261-33-4;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane;2,2'-(Perfluorocyclohexa-2,5-diene-1,4-diylidene)dimalononitrile;2,3,5,6-Tetrafluorotetracyanoquinodimethane;F4-TCNQ;2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile;C12F4N4;F4TCNQ;TCNQF4;2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane;Tetrafluorotetracyanoquinodimethane;MFCD00042382;Propanedinitrile,2,2'-(2,3,5,6-tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)bis-;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyano-quinodimethane;SCHEMBL24272;YSWG343;DTXSID10369837;AMY18874;BCP18920;AKOS005145732;CS-W010077;SB66542;AS-39315;SY050332;FT-0609419;T1131;A819843;7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane;2,3,5,6-Tetrafluoro-7,7,8,8,-tetracyano-quinodimethane;2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane, 97%;(2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile;2,2'-(2,3,5,6-Tetrafluorocyclohexa-2,5-diene-1,4-diylidene)dipropanedinitrile;Propanedinitrile, 2,2'-(2,3,5,6-tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)bis-;2-[4-(dicyanomethylene)-2,3,5,6-tetrafluoro-cyclohexa-2,5-dien-1-ylidene]propanedinitrile

Chemical Property of 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

Chemical Property:

• Appearance/Colour: yellow-greenish or orange-brown powder
• Melting Point: 285-290 °C(lit.)
• Boiling Point: -89.6±40.0 °C(Predicted)
• PSA: 95.16000
• Density: 1.57 g/cm³
• LogP: 0.63872
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 276.00590867
• Heavy Atom Count: 20
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Tetrafluorotetracyanoquinodimethane (purified by sublimation) [Organic Electronic Material] >98.0%(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(#N)C(=C1C(=C(C(=C(C#N)C#N)C(=C1F)F)F)F)C#N
• 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 .
• 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.

Technology Process of 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

There total 14 articles about 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane 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: 94.0%

2,3,5,6-tetrafluoro-1,4-benzoquinone (527-21-9,777826-79-6) + malononitrile (109-77-3) → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With pyridine; titanium tetrachloride; at 200 ℃; Temperature; Reagent/catalyst;

Reference yield: 90.0%

C24H30F4N4O2Si2 → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With triethylamine; trichlorophosphate; at 60 ℃; for 0.166667h;

Reference yield: 88.75%

C22H26F4N4O2Si2 → 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (29261-33-4)

Guidance literature:

With pyridine; phosphorus tribromide; at 100 ℃;

upstream raw materials:

2,3,5,6-Tetrafluor-1,4-bis(tert.-butyldicyanomethyl)benzol

Hexafluorobenzene

2,3,5,6-tetrafluoro-1,4-benzoquinone

malononitrile

Downstream raw materials:

octamethylferrocenium(III) perfluoro-7,7,8,8-tetracyano-p-quinodimehane radical anion

((η5-C5Me5)2Cr)2(TCNQF4)2

((η5-C5Me5)2Co)2(TCNQF4)

((η5-C5Me5)2Co)2(TCNQF4)2

Refernces

• 1、 La, Duong Duc,Ramanathan, Rajesh,Rananaware, Anushri,Bansal, Vipul,Bhosale, Sheshanath V.. "Nanostructured charge transfer complex of CuTCNQF4 for efficient photo-removal of hexavalent chromium". . p. 33931 - 33936. Retrieved 2016/05/09.