TCNQ

TCNQ

Chembox new
Name = TCNQ
ImageFile = TCNQ.png ImageSize = 100px
ImageName =
OtherNames = (2,5-Cyclohexadiene-1,4-diylidene) -dimalononitrile, 7,7,8,8-Tetracyanoquinodimethane
Section1 = Chembox Identifiers
CASNo = 1518-16-7
Section2 = Chembox Properties
Formula = C12H4N4
MolarMass = 204.19 g/mol
Appearance = rust-coloured crystals
Density =
MeltingPt = 293.5-296 °C
BoilingPt = sublimes
Solubility =
Section3 = Chembox Structure
CrystalStruct =

Solubility
organic solvents
-
Heat of fusion

-
Heat of vaporization

-
Section7 = Chembox Hazards
EUClass = not listed

Tetracyanoquinodimethane is the organic compound with the formula (NC)2CC6H4C(CN)2. This relative of para-quinone is an electron-acceptor that is used to prepare charge transfer salts, which are of interest in the area of molecular electronics.

Preparation and use

TCNQ is prepared by the condensation of 1,4-cyclohexanedione with malononitrile, followed by dehydrogenation of the resulting diene with bromine: ["Substituted Quinodimethans. I. Preparation and Chemistry of 7,7,8,8-Tetracyanoquinodimethan" J. Am. Chem. Soc. 1962, Volume 84, pp. 3370-3374. DOI|10.1021/ja00876a028] :C6H8O2 + 2 CH2(CN)2 → C6H8(C(CN)2)2 + 2 H2O:C6H8(C(CN)2)2 + 2 Br2 → C6H4(C(CN)2)2 + 4 HBr

Like TCNE, TCNQ is easily reduced electrochemically to give a blue-coloured radical anion. Upon treatment with the electron donor tetrathiafulvene (TTF), it forms the “organic metal” TTF-TCNQ where and the TCNQ is the acceptor. This salt crystallizes as a one-dimensional polymer, consisting of segregated stacks of cations and anions of the donors and the acceptors, respectively.

References


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