Skip to Content
MilliporeSigma
All Photos(1)

Documents

376779

Sigma-Aldrich

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

97%

Synonym(s):

(2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile, 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane, F4TCNQ

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12F4N4
CAS Number:
29261-33-4
Molecular Weight:
276.15
Beilstein/REAXYS Number:
2157887
MDL number:
MFCD00042382
UNSPSC Code:
12352103
PubChem Substance ID:
24863463
NACRES:
NA.23

Quality Level

100

assay

97%

form

solid

mp

285-290 °C (lit.)

SMILES string

FC1=C(F)C(\C(F)=C(F)/C1=C(\C#N)C#N)=C(\C#N)C#N

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) are p-type molecules, used as a strong acceptor dopant , it generates free holes.

Application

F4-TCNQ can be doped with poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA) to form a hole transport material (HTL), which can be used to achieve an energy efficiency of 16% for a semi-transparent perovskite solar cell. It can be used as a p-type dopant to form a blended composite film with poly(3-hexylthiophene) (P3HT) having enhanced charge mobility, which can be potentially useful in organic photovoltaics.
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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

The chemical and structural origin of efficient p-type doping in P3HT
Duong DT, et al.
Organic Electronics, 14(5), 1330-1336 (2013)
David Kiefer et al.
Nature materials, 18(2), 149-155 (2019-01-16)
Molecular doping is a crucial tool for controlling the charge-carrier concentration in organic semiconductors. Each dopant molecule is commonly thought to give rise to only one polaron, leading to a maximum of one donor:acceptor charge-transfer complex and hence an ionization
Shrawan Roy et al.
Nano letters, 18(7), 4523-4530 (2018-06-21)
Chemical treatment using bis(trifluoromethane) sulfonimide (TFSI) was shown to be particularly effective for increasing the photoluminescence (PL) of monolayer (1L) MoS2, suggesting a convenient method for overcoming the intrinsically low quantum yield of this material. However, the underlying atomic mechanism
Sungjae Cho et al.
Nature communications, 6, 7634-7634 (2015-07-15)
Aharonov-Bohm oscillations effectively demonstrate coherent, ballistic transport in mesoscopic rings and tubes. In three-dimensional topological insulator nanowires, they can be used to not only characterize surface states but also to test predictions of unique topological behaviour. Here we report measurements
John H Burke et al.
Advanced materials (Deerfield Beach, Fla.), 31(12), e1806863-e1806863 (2019-01-31)
The electron acceptor F4TCNQ p-dopes aggregates "nanowires" of poly(3-hexylthiophene) in nonpolar solvents but does not dope unaggregated chains. The standard free energy change for the charge transfer to form an ion pair is ΔG°et = -0.21 eV. The dissociation constant
View All Related Papers

Articles

Metal-Organic Complexes for Doping Organic Semiconductors and Surface Doping

The conductivity of organic semiconductors can be increased, and the barriers to charge-carrier injection from other materials can be reduced, by the use of highly reducing or oxidizing species to n- or p-dope, respectively, the semiconductor.

Soluble Pentacene Precursors

Fabrication procedure of organic field effect transistor device using a soluble pentacene precursor.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service