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Merck
CN

157635

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
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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Product Name

7,7,8,8-Tetracyanoquinodimethane, 98%

InChI key

PCCVSPMFGIFTHU-UHFFFAOYSA-N

InChI

1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H

SMILES string

N#C\C(C#N)=C1/C=C\C(C=C1)=C(/C#N)C#N

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)

Quality Level

200

Gene Information

human ... CAPN1(823)
rat ... Capn1(29153), Nos1(24598)

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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).

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000517169
0000517169
0000491032
0000491032
0000482110

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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
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)
The crystal and molecular structure of 7, 7, 8, 8-tetracyanoquinodimethane
Long, R. E., Sparks, R. A., & Trueblood, K. N.
Acta Crystallographica, 18(5), 932-939 (1965)
Williams, J.M. et al.
Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties, and Theory (1992)
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