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376779

Sigma-Aldrich

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

97%

Synonyme(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

Formule empirique (notation de Hill):
C12F4N4
Numéro CAS:
29261-33-4
Poids moléculaire :
276.15
Numéro Beilstein :
2157887
Numéro MDL:
MFCD00042382
Code UNSPSC :
12352103
ID de substance PubChem :
24863463
Nomenclature NACRES :
NA.23

Pureté

97%

Forme

solid

Pf

285-290 °C (lit.)

Chaîne SMILES 

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

Clé InChI

IXHWGNYCZPISET-UHFFFAOYSA-N

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Description générale

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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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)
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
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
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)
Afficher tous les articles scientifiques apparentés

Articles

Metal-Organic Complexes for Doping

Highly reducing or oxidizing species enhance organic semiconductor conductivity by reducing charge-carrier injection barriers.

Soluble Pentacene Precursors

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

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