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:
Molecular Weight:
204.19
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
216-174-8
Beilstein/REAXYS Number:
1427366
MDL number:
Quality Level
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)
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).
signalword
Danger
hcodes
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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Williams, J.M. et al.
Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties, and Theory (1992)
Thin film organic thermoelectric generator based on Tetrathiotetracene.
Pudzs K, et al.
Advanced Electronic Materials, 3(2), 1600429-1600429 (2017)
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)