CAS 29261-33-4 Tetrafluorotetracyanoquinodimethane (purified by sublimation) [Organic Electronic Material]

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Tetrafluorotetracyanoquinodimethane (purified by sublimation) [Organic Electronic Material]

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Catalog Number

ACM29261334-2

CAS Number

29261-33-4

Product Name

Tetrafluorotetracyanoquinodimethane (purified by sublimation) [Organic Electronic Material]

Structure

Category

Other Material Building Blocks; Molecular Conductors; Organic Field Effect Transistor (OFET) Materials

IUPAC Name

2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile

Molecular Weight

276.15g/mol

Molecular Formula

C12F4N4

Canonical SMILES

C(#N)C(=C1C(=C(C(=C(C#N)C#N)C(=C1F)F)F)F)C#N

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

InChI Key

IXHWGNYCZPISET-UHFFFAOYSA-N

Application

Tetrafluorotetracyanoquinodimethane (F4-TCNQ), purified by sublimation and presenting as a yellow-greenish or orange-brown powder, serves as a highly effective p-type dopant in organic electronic materials. Its strong electron-accepting ability and extended π system make it one of the most widely utilized dopants for hole-only devices and field-effect transistors with organic hole transport layers (HTL). F4-TCNQ's role in the formation of a bilayer structure with pentacene enhances thermoelectric performance in organic thin films. Its deep LUMO level (-5.2 eV) closely aligns with the HOMO level of many organic semiconductors, facilitating doping through charge transfer. In pin devices, F4-TCNQ doped with 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) as the p-doped HTL demonstrates remarkable luminance and efficiency at low operating voltages, achieving 1000 cd/m² at 2.9 V. Additionally, optimizing the doping concentration in PCDTBT:F4TCNQ solar cells can elevate the power conversion efficiency from 6.41% to 7.94% by enhancing photocurrent, even with an F4-TCNQ blend ratio below 0.5%. Its utility extends to serving as a p-type dopant in graphene applications as well.

Complexity

697

Covalently-Bonded Unit Count

Exact Mass

276.005909g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

276.005909g/mol

Rotatable Bond Count

XLogP3

0.2