7,7,8,8-Tetracyanoquinodimethane

Base Information

• Chemical Name: 7,7,8,8-Tetracyanoquinodimethane
• CAS No.: 1518-16-7
• Deprecated CAS: 121505-17-7,51584-70-4,51778-95-1,855786-15-1,856294-25-2,51584-70-4,51778-95-1,855786-15-1,856294-25-2
• Molecular Formula: C12H4N4
• Molecular Weight: 204.191
• Hs Code.: 29269095
• European Community (EC) Number: 216-174-8
• NSC Number: 105237
• UNII: HC6FB4H2KW
• DSSTox Substance ID: DTXSID5061748
• Nikkaji Number: J38.157H
• Wikipedia: Tetracyanoquinodimethane
• Wikidata: Q2135917
• Mol file: 1518-16-7.mol

Synonyms:7,7,8,8-tetracyanoquinodimethane;TCNQ;tetracyanoquinodimethane;tetracyanoquinonedimethane

Chemical Property of 7,7,8,8-Tetracyanoquinodimethane

Chemical Property:

• Appearance/Colour: orange to green crystalline powder
• Melting Point: 287-289 °C (dec.)(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 254.677 °C at 760 mmHg
• Flash Point: 99.674 °C
• PSA: 95.16000
• Density: 1.358 g/cm³
• LogP: 0.08232
• Storage Temp.: Store below +30°C.
• Water Solubility.: insoluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 204.043596145
• Heavy Atom Count: 16
• Complexity: 535

Purity/Quality:

95%, 99% ^*data from raw suppliers

Tetracyanoquinodimethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xn,Xi,T
• Statements: 22-20/21/22-23/24/25
• Safety Statements: 22-24/25-36/37-26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N
• Description: 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].
• Uses: 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.

Technology Process of 7,7,8,8-Tetracyanoquinodimethane

There total 45 articles about 7,7,8,8-Tetracyanoquinodimethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1.4-Bis--benzol (91268-73-4) → 7,7',8,8'-tetracyanoquinodimethane (1518-16-7,6144-37-2)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; Ambient temperature;

DOI:10.1246/cl.1985.689

Reference yield: 88.0%

2,2’-(cyclohexane-1,4-diylidene)dimalononitrile (1518-15-6) → 7,7',8,8'-tetracyanoquinodimethane (1518-16-7,6144-37-2)

Guidance literature:

With chlorine; In pyridine; acetonitrile; at 40 - 50 ℃; for 0.166667h;

DOI:10.1021/jo00156a048

Reference yield: 15.0%

1,4-bis(dicyanotrimethylsiloxymethyl)benzene (95298-05-8) → 1.4-Bis--benzol (91268-73-4) + 7,7',8,8'-tetracyanoquinodimethane (1518-16-7,6144-37-2)

Guidance literature:

With pyridine; trichlorophosphate; for 0.25h; Ambient temperature;

DOI:10.1246/cl.1985.689

upstream raw materials:

tetrathiafulvalenium radical cation

2,2’-(cyclohexane-1,4-diylidene)dimalononitrile

1.4-Bis--benzol

Dipyrido<1,2-b:1',2'-e><1,2,4,5>tetrazine / 2,2'-(Cyclohexa-2,5-dien-1,4-diyliden)bis-complex

Downstream raw materials:

1-telluracyclohexane-3,5-dione * 7,7,8,8-tetracyano-p-quinodimethane

C₁₂H₄N₄⁽¹⁺⁾

3C₁₄H₁₄N₂*2C₁₂H₈N₂*5C₁₂H₄N₄

9,9'-bifluorenyl

Refernces

• 1、 Fukuzumi, Shunichi,Urano, Tsutomu,Suenobu, Tomoyoshi. "Photoinduced charge-separation using 10-methylacridinium ion loaded in zeolite Y as a photocatalyst with negligible back electron transfer across the zeolite-solution interface". . p. 213 - 214. Retrieved 1996.
• 2、 Anikolenko et al.. "". . . Retrieved 1977.
• 3、 Melby,L.R. et al.. "-". . p. 3374 - 3387. Retrieved 1962.
• 4、 Edme, Kedy,Bettis Homan, Stephanie,Nepomnyashchii, Alexander B.,Weiss, Emily A.. "Ultrafast exciton decay in PbS quantum dots through simultaneous electron and hole recombination with a surface-localized ion pair". . p. 46 - 53. Retrieved 2016.
• 5、 Yamagishi, Akihiko,Iida, Yoichi. "Electron Transfer Reaction between Δ2,2'-Bi-1,3-dithiole (TTF) and 7,7,8,8-Tetracyanoquinodimethane (TCNQ). Electron Donating Property of TTF". . p. 1340 - 1343. Retrieved 1980.
• 6、 Ohmasa et al.. "". . p. 1998,2000. Retrieved 1968.
• 7、 Lehmann, Mark W.. "Effect of comproportionation on voltammograms for two-electron reactions with an irreversible second electron transfer". . p. 1947 - 1950. Retrieved 1999.
• 8、 Flannigan, David J.,Lobastov, Vladimir A.,Zewail, Ahmed H.. "Controlled nanoscale mechanical phenomena discovered with ultrafast electron microscopy". . p. 9206 - 9210. Retrieved 2008/12/22.