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Merck

157635

7,7,8,8-Tetracyanoquinodimethane

98%

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C12H4N4
Numéro CAS:
1518-16-7
Poids moléculaire :
204.19
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
24849689
EC Number:
216-174-8
Beilstein/REAXYS Number:
1427366
MDL number:
MFCD00011664

Principaux documents

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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)

Catégories apparentées

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000517169
0000517169
0000491032
0000491032
0000482110

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Consulter la Bibliothèque de documents

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)
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
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
Glassy carbon electrode modified with 7, 7, 8, 8-tetracyanoquinodimethane and graphene oxide triggered a synergistic effect: Low-potential amperometric detection of reduced glutathione.
Yuan B, et al.
Biosensors And Bioelectronics, 96(5), 1-7 (2017)
Nasiba Abdurakhmanova et al.
Nature communications, 3, 940-940 (2012-07-05)
Controlling supramolecular self-assembly is a fundamental step towards molecular nanofabrication, which involves a formidable reverse engineering problem. It is known that a variety of structures are efficiently obtained by assembling appropriate organic molecules and transition metal atoms on well-defined substrates.
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