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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

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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Die Dokumentenbibliothek aufrufen

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)
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)
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
Yuuta Yano et al.
Nature, 571(7765), 387-392 (2019-06-28)
The properties of graphene nanoribbons (GNRs)1-5-such as conductivity or semiconductivity, charge mobility and on/off ratio-depend greatly on their width, length and edge structure. Existing bottom-up methods used to synthesize GNRs cannot achieve control over all three of these parameters simultaneously
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