Skip to Content
MilliporeSigma

376779

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

97%

Synonym(s):

(2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile, 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane, F4TCNQ

Slide 1 of 1
Sign In to View Organizational & Contract Pricing

Select a Size

25 MG

$118.00

100 MG

$336.00

$118.00

Check Cart for Availability
Need it sooner? View alternative products.
Request a Bulk Order

About This Item

Empirical Formula (Hill Notation):
C12F4N4
CAS Number:
29261-33-4
Molecular Weight:
276.15
Beilstein/REAXYS Number:
2157887
MDL number:
MFCD00042382
UNSPSC Code:
12352103
PubChem Substance ID:
24863463
NACRES:
NA.23

Key Documents

View All Documentation

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

assay

97%

form

solid

mp

285-290 °C (lit.)

SMILES string

FC1=C(F)C(\C(F)=C(F)/C1=C(\C#N)C#N)=C(\C#N)C#N

InChI

1S/C12F4N4/c13-9-7(5(1-17)2-18)10(14)12(16)8(11(9)15)6(3-19)4-20

Inchi Key

IXHWGNYCZPISET-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
157635232017196819
2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane 97%

Sigma-Aldrich

376779

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane

7,7,8,8-Tetracyanoquinodimethane 98%

Sigma-Aldrich

157635

7,7,8,8-Tetracyanoquinodimethane

Tetrachloro-1,4-benzoquinone 99%

Sigma-Aldrich

232017

Tetrachloro-1,4-benzoquinone

Tetrafluorophthalonitrile 95%

Sigma-Aldrich

196819

Tetrafluorophthalonitrile

assay

97%

assay

98%

assay

99%

assay

95%

form

solid

form

solid

form

solid

form

-

mp

285-290 °C (lit.)

mp

287-289 °C (dec.) (lit.)

mp

289 °C (dec.) (lit.)

mp

81-86 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

General description

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) is a dopant used in the fabrication of organic semiconductors. It can tune the electronic properties as its lowest unoccupied molecular orbital is at a desirable energy level required to oxidize a wide range of semiconductors.[1]
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) are p-type molecules, used as a strong acceptor dopant , it generates free holes.[2][3]

Application

F4-TCNQ can be doped with poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA) to form a hole transport material (HTL), which can be used to achieve an energy efficiency of 16% for a semi-transparent perovskite solar cell.[4][5] It can be used as a p-type dopant to form a blended composite film with poly(3-hexylthiophene) (P3HT) having enhanced charge mobility, which can be potentially useful in organic photovoltaics.[6][7]
F4-TCNQ is the p-type dopant for hole-only devices and field effect transistors with organic hole transport layers (HTL).[2] It is used in the preparation of a bilayer structure of F4-TCNQ and pentacene to study improved thermoelectric performance of organic thin films.[3]

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCL6117
MKBT6172V
MKBR4717V
MKBR4863V
MKBR1477V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Dual-Source Precursor Approach for Highly Efficient Inverted Planar Heterojunction Perovskite Solar Cells
Luo D, et al.
Advanced Materials, 29(19), 1604758-1604758 (2017)
Hans He et al.
Nature communications, 9(1), 3956-3956 (2018-09-29)
Tuning the charge carrier density of two-dimensional (2D) materials by incorporating dopants into the crystal lattice is a challenging task. An attractive alternative is the surface transfer doping by adsorption of molecules on 2D crystals, which can lead to ordered
A simple method for controllable solution doping of complete polymer field-effect transistors
Ingram IDV, et al.
Applied Physics Letters, 104(15), 581-581 (2014)
Sungjae Cho et al.
Nature communications, 6, 7634-7634 (2015-07-15)
Aharonov-Bohm oscillations effectively demonstrate coherent, ballistic transport in mesoscopic rings and tubes. In three-dimensional topological insulator nanowires, they can be used to not only characterize surface states but also to test predictions of unique topological behaviour. Here we report measurements
David Kiefer et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 4(1), 1600203-1600203 (2017-01-21)
Poly(ethylene oxide) is demonstrated to be a suitable matrix polymer for the solution-doped conjugated polymer poly(3-hexylthiophene). The polarity of the insulator combined with carefully chosen processing conditions permits the fabrication of tens of micrometer-thick films that feature a fine distribution
View All Related Papers

Articles

Metal-Organic Complexes for Doping

Highly reducing or oxidizing species enhance organic semiconductor conductivity by reducing charge-carrier injection barriers.

Soluble Pentacene Precursors

Fabrication procedure of organic field effect transistor device using a soluble pentacene precursor.

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service