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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:
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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
(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)
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