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157635

Sigma-Aldrich

7,7,8,8-Tetracyanochinodimethan

98%

Synonym(e):

(2,5-Cyclohexadien-1,4-diyliden)-dimalononitril, TCNQ

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About This Item

Empirische Formel (Hill-System):
C12H4N4
CAS-Nummer:
1518-16-7
Molekulargewicht:
204.19
Beilstein:
1427366
EG-Nummer:
216-174-8
MDL-Nummer:
MFCD00011664
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24849689
NACRES:
NA.23

Qualitätsniveau

200

Assay

98%

Form

solid

mp (Schmelzpunkt)

287-289 °C (dec.) (lit.)

Energie der Orbitale

LUMO 4.6 eV 

Halbleitereigenschaften

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

InChIKey

PCCVSPMFGIFTHU-UHFFFAOYSA-N

Angaben zum Gen

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

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Verwandte Kategorien

Allgemeine Beschreibung

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.

Anwendung

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).

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Lagerklassenschlüssel

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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)
Thermoelectric Properties of Poly (3-hexylthiophene)(P3HT) Doped with 2, 3, 5, 6-Tetrafluoro-7, 7, 8, 8-tetracyanoquinodimethane (F4TCNQ) by Vapor-Phase Infiltration.
Lim E, et al.
Chemistry of Materials, 30(3), 998-1010 (2018)
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
Williams, J.M. et al.
Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties, and Theory (1992)
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