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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/REAXYS Number:
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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Thin film organic thermoelectric generator based on Tetrathiotetracene.
Pudzs K, et al.
Advanced Electronic Materials, 3(2), 1600429-1600429 (2017)
Williams, J.M. et al.
Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties, and Theory (1992)
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)
Jinchong Xiao et al.
Small (Weinheim an der Bergstrasse, Germany), 7(9), 1242-1246 (2011-04-16)
The chemical reaction between Ag nanoparticles (Ag NPs) and 7,7',8,8'- tetracycanoquinodimethane (TCNQ) microparticles (MPs) in aqueous solution for the formation of Ag-NP-decorated Ag-TCNQ nanowires is reported. Based on the results obtained by UV-vis spectroscopy and scanning electron microscopy (SEM), it
Electrochemical and X-ray diffraction study of the redox cycling of nanocrystals of 7, 7, 8, 8-tetracyanoquinodimethane. Observation of a solid-solid phase transformation controlled by nucleation and growth.
Bond, A. M., Fletcher, S., Marken, F., Shaw, S. J., & Symons, P. G.
J. Chem. Soc., Faraday, 92(20), 3925-3933 (1996)
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