Tetracyanoquinodimethane

Structural formula
General
Surname	Tetracyanoquinodimethane
other names	TCNQ 7,7,8,8-tetracyanoquinodimethane Tetracyanoquinodimethane Tetracyanoquinodimethane Tetracyano-p-quinodimethane (2,5-Cyclohexadiene-1,4-diylidene) -dimalononitrile
Molecular formula	C 12 H 4 N 4
Brief description	dark brown crystals
External identifiers / databases
CAS number 1518-16-7 EC number 216-174-8 ECHA InfoCard 100.014.704 PubChem 73697 Wikidata Q2135917
properties
Molar mass	204.19 g mol −1
Physical state	firmly
Melting point	287–289 ° C (decomposition)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-311-331 P: 261-280-301 + 310-311
Toxicological data	56 mg kg −3 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetracyanoquinodimethane (TCNQ) is an organic substance which is related to 1,4-benzoquinone and is an organic semiconductor material . The nitrile is an electron acceptor ; that is, it easily accepts an electron, thereby forming an anion with an unpaired electron, a radical anion . This radical ion is unusually stable because it contains an aromatic nucleus . Tetracyanoquinodimethane forms adducts with many aromatic electron donors, which have an exceptionally high electrical conductivity; they are electron conductors. The substance class of the adducts of tetracyanoquinodimethane and their conductivity has been extremely well investigated; In 1977 it was considered to be better studied than all other organic conductive salts combined. In combination with tetrathiafulvalene (TTF), single crystals with good electrical conductivity are formed .

In technical applications, TCNQ is the starting material for organic plastic magnet materials such as PANiCNQ . Until it was discontinued by Panasonic in 2010, TCNQ had another application in the OS-CON named polymer electrolytic capacitors as a so-called " solid electrolyte ".

Individual evidence

1. ↑ ^{a b c d e} data sheet 7,7,8,8- tetracyanoquinodimethane, 98% from Sigma-Aldrich , accessed on June 6, 2013 ( PDF ).
2. ↑ ^{a b c} Jerome H. Perlstein: "Organic Metals" - The Intermolecular Migration of Aromaticity . In: Society of German Chemists / John Wiley & Sons (ed.): Angewandte Chemie . tape 89 , no. 8 , 1977, ISSN  1521-3757 , pp. 534-549 , doi : 10.1002 / anie.19770890807 .
3. ↑ John. Ferraris, DO Cowan, V. Walatka, JH Perlstein: Electron transfer in a new highly conducting donor-acceptor complex . In: Journal of the American Chemical Society . tape 95 , no. 3 , February 1973, p. 948-949 , doi : 10.1021 / ja00784a066 .
4. ↑ F. Wudl: From organic metals to superconductors: managing conduction electrons in organic solids . In: Accounts of Chemical Research . tape 17 , no. 6 , 1984, pp. 227-232 , doi : 10.1021 / ar00102a005 .
5. ^ Naveed A. Zaidi, SR Giblin, I. Terry, AP Monkman: Room temperature magnetic order in an organic magnet derived from polyaniline . In: polymer . tape 45 , no. 16 , July 21, 2004, p. 5683-5689 , doi : 10.1016 / j.polymer.2004.06.002 .
6. ↑ New OS-CON Capacitors, Aluminum-Polymer Solid Capacitors; Panasonic [1]