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376779 Sigma-Aldrich

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

97%

Synonym: (2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile, 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane, F4TCNQ

  • CAS Number 29261-33-4

  • Empirical Formula (Hill Notation) C12F4N4

  • Molecular Weight 276.15

  •  Beilstein/REAXYS Number 2157887

  •  MDL number MFCD00042382

  •  PubChem Substance ID 24863463

  •  NACRES NA.23

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Properties

Related Categories Hole Injection Layer (HIL) Materials, Hole Transport (HT) & Hole Injection Layer (HIL) Materials, Materials Science, NLO Chromophores and Intermediates, Non-Linear Optical (NLO) Materials,
assay   97%
mp   285-290 °C (lit.)
storage temp.   room temp
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

Description

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.

Packaging

25, 100 mg in glass insert

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

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-...
Stephen Barlow and Seth R. Marder
Center for Organic Photonics and Electronics and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
Keywords: Chemical reactions, Deposition, Diffusion, Evaporation, Nitrogen phosphorus detector, Phase transitions, Photovoltaics, Redox Reactions, Reductions, Semiconductor, Solvents, Spectroscopy, Sublimation

Soluble Pentacene Precursors

In order to introduce un-functionalized pentacene within a device such as an organic field effect transistor (OFET), soluble pentacene precursors, which readily transform into pentacene upon heating ...
Prof. Cherie R. Kagan

Associate Professor, Department of Materials Science and Engineering,
University of Pennsylvania, Philadelphia, PA 19104
Keywords: Deposition, Evaporation, Semiconductor, Size-exclusion chromatography

Peer-Reviewed Papers
15

References

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