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1518-16-7

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1518-16-7 Usage

Applications

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. It also has been shown that TCNQ can effectively modify Cu or Ag surfaces. The formation of Cu-TCNQ and Ag-TCNQ enhances the work function of such electrodes and reduces the hole injection barrier dramatically. Furthermore, it improves electrode/organic layer contact, hence the reduction of contact resistances. Tetracyanoquinodimethane (TCNQ) is also found to act as a p-type doping agent of graphene films due to its powerful electron-accepting capacity.

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].

Chemical Properties

orange to green crystalline powder

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.

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/ja00876a028The Journal of Organic Chemistry, 48, p. 1366, 1983 DOI: 10.1021/jo00156a048

General Description

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.

Check Digit Verification of cas no

The CAS Registry Mumber 1518-16-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,1 and 8 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1518-16:
(6*1)+(5*5)+(4*1)+(3*8)+(2*1)+(1*6)=67
67 % 10 = 7
So 1518-16-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H4/c1-2-4-6-5-3-1/h1-2,5-6H

1518-16-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (A10779)  7,7,8,8-Tetracyanoquinodimethane, 98%   

  • 1518-16-7

  • 5g

  • 640.0CNY

  • Detail
  • Alfa Aesar

  • (A10779)  7,7,8,8-Tetracyanoquinodimethane, 98%   

  • 1518-16-7

  • 25g

  • 2723.0CNY

  • Detail
  • Alfa Aesar

  • (A10779)  7,7,8,8-Tetracyanoquinodimethane, 98%   

  • 1518-16-7

  • 100g

  • 9510.0CNY

  • Detail
  • Aldrich

  • (157635)  7,7,8,8-Tetracyanoquinodimethane  98%

  • 1518-16-7

  • 157635-5G

  • 1,009.71CNY

  • Detail
  • Aldrich

  • (157635)  7,7,8,8-Tetracyanoquinodimethane  98%

  • 1518-16-7

  • 157635-10G

  • 1,857.96CNY

  • Detail

1518-16-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name tetracyanoquinodimethane

1.2 Other means of identification

Product number -
Other names 7,7,8,8-Tetracyanoquinodimethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1518-16-7 SDS

1518-16-7Relevant articles and documents

Hosaka et al.

, p. 2616 (1971)

MECHANISM OF THE HYDRIDE TRANSFER REACTION OF LEUCO CRYSTAL VIOLET WITH CYANOMETHYLENE ACCEPTORS

Nishimura, Norio,Zaman, Khan M.,Yamamoto, Shunzo

, p. 218 - 220 (1994)

In the hydride transfer reaction of Leuco Crystal Violet to form the Crystal Violet cation, the role of cyanomethylene acceptors was found to be essentially different from that of p-benzoquinones, both previously believed to act as ?-acceptors in the same manner.

Acker et al.

, p. 6408 (1960)

Boyd

, p. 2529,2531, 2533 (1963)

Microelectrochemical measurements of electron transfer rates at the interface between two immiscible electrolyte solutions: Potential dependence of the ferro/ferricyanide-7,7,8,8-tetracyanoquinodimethane (TCNQ)/TCNQ?- system

Unwin,Zhang

, p. 3820 - 3827 (2002)

The reduction of 7,7,8,8-tetracyanoquinodimethane (TCNQ) in 1,2-dichloromethane (DCE) and nitrobenzene (NB), by aqueous ferrocyanide, and the back reaction were studied by scanning electrochemical microscopy. The effect of galvanic potential at the interface between two immiscible electrolyte solutions (ITIES) on electron transfer (ET) rates, with different electrolyte concentrations in the organic phase was evaluated. The ET rate constants for the forward and back reaction depended strongly on the interfacial potential drop, with an apparent ET coefficient close to 0.5. TCNQ?- was confined to DCE, but transferred from NB to water under certain experimental conditions, which could complicate kinetic analysis. The ET kinetics for the water/DCE system were analyzed further using Marcus theory. Close to zero driving force, the rate constants for the forward and back reaction were similar and in good agreement with predictions from Marcus theory with a sharp liquid/liquid interface. At equilibrium (when the forward and back ET rate constants were equal), the sharp boundary model for the ITIES predicted a bimolecular rate constant close to that measured experimentally.

Electrically conducting TCNQ Derivatives of Copper Sulphur/Nitrogen Chelates; Structure of a Novel Semiconducting Complex 2 which contains N-bonded TCNQ (pdto=1,8-di-2-pyridyl-3,6-dithiaoctane; TCNQ=7,7,8,8-tetracyanoquinodimethane)

Humphrey, David G.,Fallon, Gary D.,Murray, Keith S.

, p. 1356 - 1358 (1988)

Reaction in water of Cu(pdto)(ClO4)2 with Li(TCNQ)/TCNQ mixtures yields solid crystalline materials of formulae Cu(pdto)(TCNQ)x (x=2, 2.5, or 3) which display high electrical conductivities ; reaction of Cu(pdto)(ClO4) with Li(TCNQ) yields Cu(pdto)(TCNQ), a poor conductor which has been shown by X-ray crystallography to have a novel dimeric structure involving ?-? interaction between TCNQ units and which possesses Cu-TCNQ bonding.

Positive dendritic effects on the electron-donating potencies of poly(propylene imine) dendrimers

Ong, Winston,McCarley, Robin L.

, p. 1287 - 1290 (2005)

(Chemical Equation Presented) Two series of poly(propylene imine), PPI, dendrimers terminated with a redox-active donor, 4-dimethylaminobenzyl (4-DMAB), including their respective nondendronized model compounds, are reported. In these two series, a positive dendritic effect was observed for the formation of charge-transfer (CT) complexes between the dendrimers and 7,7,8,8- tetracyanoquinodimethane (TCNQ). However, the nondendronized compounds did not form CT complexes with TCNQ, even though their redox potentials are similar to those of the 4-DMAB units attached to the dendrimers.

Spectroscopic and thermal investigations on the charge transfer interaction between risperidone as a schizophrenia drug with some traditional π-acceptors: Part 2

El-Habeeb, Abeer A.,Al-Saif, Foziah A.,Refat, Moamen S.

, p. 464 - 477 (2013/04/23)

The focus of present investigation was to assess the utility of non-expensive techniques in the evaluation of risperidone (Ris) in solid and solution states with different traditional π-acceptors and subsequent incorporation of the analytical determination into pharmaceutical formulation for a faster release of risperidone. Charge-transfer complexes (CTC) of risperidone with picric acid (PA), 2,3-dichloro-5,6-dicyano-p-benzoquinon (DDQ), tetracyanoquinodimethane (TCNQ), tetracyano ethylene (TCNE), tetrabromo-p-quinon (BL) and tetrachloro-p-quinon (CL) have been studied spectrophotometrically in absolute methanol at room temperature. The stoichiometries of the complexes were found to be 1:1 ratio by the photometric molar ratio between risperidone and the π-acceptors. The equilibrium constants, molar extinction coefficient (εCT) and spectroscopic-physical parameters (standard free energy (ΔGo), oscillator strength (f), transition dipole moment (μ), resonance energy (RN) and ionization potential (ID)) of the complexes were determined upon the modified Benesi-Hildebrand equation. Risperidone in pure form was applied in this study. The results indicate that the formation constants for the complexes depend on the nature of electron acceptors and donor, and also the spectral studies of the complexes were determined by (infrared, Raman, and 1H NMR) spectra and X-ray powder diffraction (XRD). The most stable mono-protonated form of Ris is characterized by the formation of +NH (pyrimidine ring) intramolecular hydrogen bonded. In the high-wavenumber spectral region ~3400 cm-1, the bands of the +NH stretching vibrations and of the pyrimidine nitrogen atom could be potentially useful to discriminate the investigated forms of Ris. The infrared spectra of both Ris complexes are confirming the participation of +NH pyrimidine ring in the donor-acceptor interaction.

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