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

Melting point:

285-290 °C(lit.)

Boiling point:

-89.6±40.0 °C(Predicted)

Density 

1.7075 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light yellow to Amber to Dark green

Water Solubility 

insoluble

BRN 

2157887

InChI

InChI=1S/C12F4N4/c13-9-7(5(1-17)2-18)10(14)12(16)8(11(9)15)6(3-19)4-20

InChIKey

IXHWGNYCZPISET-UHFFFAOYSA-N

SMILES

C1(=C(C#N)C#N)C(F)=C(F)C(=C(C#N)C#N)C(F)=C1F |c:10,t:0|

CAS DataBase Reference

29261-33-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T

Risk 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

Hazard Note 

Toxic

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane Usage And Synthesis

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.

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