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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

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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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL6117
MKBT6172V
MKBR4717V
MKBR4863V
MKBR1477V

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A simple method for controllable solution doping of complete polymer field-effect transistors
Ingram IDV, et al.
Applied Physics Letters, 104(15), 581-581 (2014)
Yingying Liang et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 7(3), 1902456-1902456 (2020-02-12)
Three isostructural donor-acceptor complexes DPTTA-F X
Improved thermoelectric performance of organic thin-film elements utilizing a bilayer structure of pentacene and 2, 3, 5, 6-tetrafluoro-7, 7, 8, 8-tetracyanoquinodimethane (F 4-TCNQ).
Applied Physics Letters, 96(25) (2010)
Taiki Sawada et al.
Nature communications, 11(1), 4839-4839 (2020-09-26)
Transistors, the most important logic elements, are maintained under dynamic influence during circuit operations. Practically, circuit design protocols and frequency responsibility should stem from a perfect agreement between the static and dynamic properties. However, despite remarkable improvements in mobility for
David Kiefer et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 4(1), 1600203-1600203 (2017-01-21)
Poly(ethylene oxide) is demonstrated to be a suitable matrix polymer for the solution-doped conjugated polymer poly(3-hexylthiophene). The polarity of the insulator combined with carefully chosen processing conditions permits the fabrication of tens of micrometer-thick films that feature a fine distribution
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