Tetracyanoquinodimethane
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Tetracyanoquinodimethane | |||||||||||||||
other names |
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Molecular formula | C 12 H 4 N 4 | |||||||||||||||
Brief description |
dark brown crystals |
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properties | ||||||||||||||||
Molar mass | 204.19 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
287–289 ° C (decomposition) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
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
- ↑ a b c d e data sheet 7,7,8,8- tetracyanoquinodimethane, 98% from Sigma-Aldrich , accessed on June 6, 2013 ( PDF ).
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ^ 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 .
- ↑ New OS-CON Capacitors, Aluminum-Polymer Solid Capacitors; Panasonic [1]