Home Categories 7,7,8,8-Tetracyanoquinodimethane
A7693212

7,7,8,8-Tetracyanoquinodimethane , 98% , 1518-16-7

Synonym(s):
(2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile;TCNQ;TCNQ, 1,4-Bis(dicyanomethylene)-2,5-cyclohexadiene

CAS NO.:1518-16-7

Empirical Formula: C12H4N4

Molecular Weight: 204.19

MDL number: MFCD00011664

EINECS: 216-174-8

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1g RMB239.20 In Stock
5G RMB559.20 In Stock
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Update time: 2022-07-08

PRODUCT Properties

Melting point: 287-289 °C (dec.) (lit.)
Boiling point: 332.67°C (rough estimate)
Density  1.3596 (rough estimate)
refractive index  1.5000 (estimate)
storage temp.  Sealed in dry,Room Temperature
form  Crystalline Powder
color  Orange-brown to green
Water Solubility  insoluble
λmax 395nm(CH3CN)(lit.)
BRN  611604
Stability: Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents.
InChI 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
SMILES C1(=C(C#N)C#N)C=CC(=C(C#N)C#N)C=C1 |c:8,t:0|
CAS DataBase Reference 1518-16-7(CAS DataBase Reference)
NIST Chemistry Reference Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7)
EPA Substance Registry System Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7)

Description and Uses

7,7,8,8-tetracyanoquinodimethane (TCNQ), with a LUMO at 4.5 eV, is known for the charge-transfer salts formed by its radical anion TCNQ in?photovoltaic, light-emitting diodes, and organic field-effect transistor?devices. TCNQ and its derivatives?have been used as dopants, leading to an increase in hole mobility or to the lowering of injection?barriers. One classic example of such is the treatment of tetrathiafulvene (TTF), an electron donor with TCNQ. TFF and TCNQ form an ion pair, the TTF-TCNQ complex. This process of doping leads to the crystallisation of the ion pair into a one-dimensionally stacked polymer. This polymer consists of segregated stacks of cations and anions of the donors and the acceptors, respectively. The complex crystal is an organic semiconductor that exhibits metallic electric conductivity [1, 2].

7,7,8,8-Tetracyanoquinodimethane is an electron-acceptor molecule used to form charge-transfer superconductors. It is an effective catalyst used for the ?-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination.

Safety

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301+H311+H331
Precautionary statements  P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazard Codes  Xn,Xi,T
Risk Statements  22-20/21/22-23/24/25
Safety Statements  22-24/25-36/37-26-36-45
RIDADR  3276
WGK Germany  3
RTECS  GU4850000
Hazard Note  Irritant
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29269095

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