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157635 Sigma-Aldrich

7,7,8,8-Tetracyanoquinodimethane

98%

Synonym: (2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile, TCNQ

  • CAS Number 1518-16-7

  • Empirical Formula (Hill Notation) C12H4N4

  • Molecular Weight 204.19

  •  Beilstein/REAXYS Number 1427366

  •  EC Number 216-174-8

  •  MDL number MFCD00011664

  •  PubChem Substance ID 24849689

  •  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,
Quality Level   200
assay   98%
mp   287-289 °C (dec.) (lit.)
Orbital energy   LUMO 4.6 eV 
semiconductor properties   N-type (mobility=10−5 cm2/V·s)
SMILES string   N#C\C(C#N)=C1/C=C\C(C=C1)=C(/C#N)C#N
InChI   1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
InChI key   PCCVSPMFGIFTHU-UHFFFAOYSA-N
Gene Information   human ... CAPN1(823)
rat ... Capn1(29153), Nos1(24598)

Description

General description

7,7,8,8-Tetracyanoquinodimethane (TNCQ) is a strong electron acceptor as it has four cyano groups and π-conjugation bonds that form charge transferring chains and ion radical salts which are mainly used as p-dopants for the fabrication of a variety of semiconductor applications.

Application

Electron-acceptor molecule used to form charge-transfer superconductors.

Tetrathiotetracene (TTT) and TNCQ can be thermally co-deposited to form n-type thin films with a power factor of 0.33 μWm-1K-2 and an electrical conductivity of 57 Sm-1 to fabricate thin film organic thermoelectric generators. It can be used to functionalize chemical vapor deposited (CVD) graphene and form a p-doped nanocomposite that finds potential application as a conductive anode for organic solar cells (OSCs). Electrochemical sensors can be developed by using TNCQ and graphene oxide to form a glassy electrode for the detection of reduced glutathione (GSH).

Packaging

10 g in poly bottle

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
UN 3439A 6.1 / PGI
WGK Germany 
WGK 3
RTECS 
GU4850000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

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

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Lab Chemicals

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Keywords: Gas chromatography, Infrared spectroscopy, Sublimation, Thin layer chromatography

Peer-Reviewed Papers
15

References

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