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Merck

157635

7,7,8,8-Tetracyanoquinodimethane

98%

Synonym(s):

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

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About This Item

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

Key Documents

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Quality Level

200

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)

Related Categories

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Deleterious substance

pdsc

157635-10G:4.548173108186E12 + 157635-1G:4.548173108193E12 + 157635-5G:4.548173108209E12

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Certificates of Analysis (COA)

Lot/Batch Number
455372/1
05625DB
S37632
10405HY
06011LS

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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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