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Merck

157635

Sigma-Aldrich

7,7,8,8-Tetracyanoquinodimethane

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C12H4N4
Número de CAS:
Peso molecular:
204.19
Beilstein/REAXYS Number:
1427366
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

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

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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

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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Rajsapan Jain et al.
Nature, 445(7125), 291-294 (2007-01-19)
For over two decades there have been intense efforts aimed at the development of alternatives to conventional magnets, particularly materials comprised in part or wholly of molecular components. Such alternatives offer the prospect of realizing magnets fabricated through controlled, low-temperature
Characterisation of two distinctly different processes associated with the electrocrystallization of microcrystals of phase I CuTCNQ (TCNQ= 7, 7, 8, 8-tetracyanoquinodimethane)
Harris, Alexander R., et al.
Journal of Materials Chemistry, 16(45), 4397-4406 (2006)
Liang Pan et al.
Nature communications, 11(1), 1332-1332 (2020-03-14)
Compared to transmission systems based on shafts and gears, tendon-driven systems offer a simpler and more dexterous way to transmit actuation force in robotic hands. However, current tendon fibers have low toughness and suffer from large friction, limiting the further
(Pro2 H+)2 (TCNQ.-)2⋅TCNQ: an amino acid derived semiconductor.
Xiaohu Qu et al.
Angewandte Chemie (International ed. in English), 50(7), 1589-1592 (2011-02-11)
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)

Artículos

Fabrication procedure of organic field effect transistor device using a soluble pentacene precursor.

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