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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:
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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL6117
MKBT6172V
MKBR4717V
MKBR4863V
MKBR1477V

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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
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
The chemical and structural origin of efficient p-type doping in P3HT
Duong DT, et al.
Organic Electronics, 14(5), 1330-1336 (2013)
Jack Fuzell et al.
The journal of physical chemistry letters, 7(21), 4297-4303 (2016-11-04)
Doping-induced solubility control (DISC) is a recently introduced photolithographic technique for semiconducting polymers, which utilizes reversible changes in polymer solubility upon doping to allow the polymer to function as its own photoresist. Central to this process is a wavelength sensitive
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)
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