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157635

Sigma-Aldrich

7,7,8,8-Tetracyanoquinodimethane

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H4N4
CAS Number:
1518-16-7
Molecular Weight:
204.19
Beilstein:
1427366
EC Number:
216-174-8
MDL number:
MFCD00011664
UNSPSC Code:
12352103
PubChem Substance ID:
24849689
NACRES:
NA.23

Assay

98%

form

solid

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)

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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).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Growth and characterization of 7, 7, 8, 8-tetracyano-quinodimethane crystals on chemical vapor deposition graphene.
Black A, et al.
Journal of Crystal Growth, 453(2), 1-6 (2016)
Thermoelectric Properties of Poly (3-hexylthiophene)(P3HT) Doped with 2, 3, 5, 6-Tetrafluoro-7, 7, 8, 8-tetracyanoquinodimethane (F4TCNQ) by Vapor-Phase Infiltration.
Lim E, et al.
Chemistry of Materials, 30(3), 998-1010 (2018)
Charge-transfer Complex Formed with Bowl-shaped Corannulene as Electron Donor and Planar 7, 7, 8, 8-Tetracyanoquinodimethane as Electron Acceptor.
Yoshida Y, et al.
Chemistry Letters (Jpn), 44(5), 709-711 (2015)
Alexander Mityashin et al.
Advanced materials (Deerfield Beach, Fla.), 24(12), 1535-1539 (2012-03-01)
The mechanism by which molecular dopants donate free charge carriers to the host organic semiconductor is investigated and is found to be quite different from the one in inorganic semiconductors. In organics, a strong correlation between the doping concentration and
Williams, J.M. et al.
Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties, and Theory (1992)
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