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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
Beilstein:
2157887
Numéro MDL:
MFCD00042382
Code UNSPSC :
12352103
ID de substance PubChem :
24863463
Nomenclature NACRES :
NA.23

Niveau de qualité

100

Essai

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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Catégories apparentées

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCL6117
MKBT6172V
MKBR4717V
MKBR4863V
MKBR1477V

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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
Afficher tous les articles scientifiques apparentés

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.

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