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376779

Sigma-Aldrich

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

97%

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C12F4N4
Número de CAS:
29261-33-4
Peso molecular:
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

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

Certificados de análisis (COA)

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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)
Enhancing hole transports and generating hole traps by doping organic hole-transport layers with p-type molecules of 2, 3, 5, 6-tetrafluoro-7, 7, 8, 8-tetracyanoquinodimethane
Matsushima T and Adachi C
Thin Solid Films, 517(2), 874-877 (2008)
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
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
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
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