7,7,8,8-Tetracyanoquinodimethane Struktur

2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril

Bezeichnung:2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril

CAS-Nr1518-16-7

Englisch Name:7,7,8,8-Tetracyanoquinodimethane

CBNumberCB6306980

SummenformelC12H4N4

Molgewicht204.19

MOL-Datei1518-16-7.mol

Synonyma

2,2'-(2,5-Cyclohexadien-1,4-diyliden)bismalononitril

2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril

2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril physikalisch-chemischer Eigenschaften

Schmelzpunkt	287-289 °C (dec.) (lit.)
Siedepunkt	332.67°C (rough estimate)
Dichte	1.3596 (rough estimate)
Brechungsindex	1.5000 (estimate)
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	Crystalline Powder
Farbe	Orange-brown to green
Wasserlöslichkeit	insoluble
maximale Wellenlänge (λmax)	395nm(CH3CN)(lit.)
BRN	611604
Stabilität	Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents.
CAS Datenbank	1518-16-7(CAS DataBase Reference)
NIST chemische Informationen	Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7)
EPA chemische Informationen	Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi,T
R-Sätze:	22-20/21/22-23/24/25
S-Sätze:	22-24/25-36/37-26-36-45
RIDADR	3276
WGK Germany	3
RTECS-Nr.	GU4850000
Hazard Note	Irritant
TSCA	Yes
HazardClass	6.1
PackingGroup	II
HS Code	29269095

Gefahreninformationscode (GHS)

7,7,8,8-Tetracyanoquinodimethane Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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].
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
orange to green crystalline powder
Verwenden
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.
Definition
ChEBI: A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups.
Synthesis Reference(s)
Journal of the American Chemical Society, 84, p. 3370, 1962 DOI: 10.1021/ja00876a028
The Journal of Organic Chemistry, 48, p. 1366, 1983 DOI: 10.1021/jo00156a048
Allgemeine Beschreibung
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.

7,7,8,8-Tetracyanoquinodimethane Upstream-Materialien And Downstream Produkte

2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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