Tetracyanoquinodimethane (TCNQ) is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula . This

cyanocarbon In organic chemistry, cyanocarbons are a group of chemical compounds that contain several cyanide functional groups. Such substances generally are classified as organic compounds, since they are formally derived from hydrocarbons by replacing one ...

, a relative of para-quinone, is an

electron acceptor An electron acceptor is a chemical entity that accepts electrons transferred to it from another compound. It is an oxidizing agent that, by virtue of its accepting electrons, is itself reduced in the process. Electron acceptors are sometimes mista ...

that is used to prepare charge transfer salts, which are of interest in

molecular electronics Molecular electronics is the study and application of molecular building blocks for the fabrication of electronic components. It is an interdisciplinary area that spans physics, chemistry, and materials science. The unifying feature is use of mo ...

Preparation and structure

TCNQ is prepared by the

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...

of 1,4-cyclohexanedione with

malononitrile Malononitrile is an organic compound nitrile with the formula . It is a colorless or white solid. It can be prepared by dehydration of cyanoacetamide. Malononitrile is relatively acidic, with a p''K''a of 11 in water. This allows it to be used ...

, followed by

dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...

of the resulting diene with

bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...

: : : The molecule is planar, with D_2h

symmetry Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definit ...

Reactions

tetracyanoethylene Tetracyanoethylene (TCNE) is organic compound with the formula . It is a colorless solid, although samples are often off-white. It is an important member of the cyanocarbons. Synthesis and reactions TCNE is prepared by brominating malononitrile ...

(TCNE), TCNQ is easily reduced to give a blue-coloured radical anion. The reduction potential is about −0.3 V relative to the ferrocene/ferrocenium couple. This property is exploited in the development of charge transfer salts. TCNQ also forms complexes with electron-rich metal complexes.

Charge transfer salts

TCNQ achieved great attention because it forms charge-transfer salts with high electrical conductivity. These discoveries were influential in the development of

organic electronics Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorga ...

. Illustrative is the product from treatment of TCNQ with the

electron donor In chemistry, an electron donor is a chemical entity that donates electrons to another compound. It is a reducing agent that, by virtue of its donating electrons, is itself oxidized in the process. Typical reducing agents undergo permanent chem ...

tetrathiafulvene Tetrathiafulvalene is an organosulfur compound with the formula (. Studies on this heterocyclic compound contributed to the development of molecular electronics. TTF is related to the hydrocarbon fulvalene, , by replacement of four CH groups wit ...

(TTF), TCNQ forms an ion pair, the TTF-TCNQ complex, in which TCNQ is the acceptor. This salt crystallizes in a one-dimensionally stacked polymer, consisting of segregated stacks of cations and anions of the donors and the acceptors, respectively. The complex crystal is an

organic semiconductor Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or ...

that exhibits metallic

electric conductivity Electrical resistivity (also called specific electrical resistance or volume resistivity) is a fundamental property of a material that measures how strongly it resists electric current. A low resistivity indicates a material that readily allow ...

Related compounds

Tetracyanoethylene Tetracyanoethylene (TCNE) is organic compound with the formula . It is a colorless solid, although samples are often off-white. It is an important member of the cyanocarbons. Synthesis and reactions TCNE is prepared by brominating malononitrile ...

, another

that functions as an electron acceptor.

References

{{reflist Nitriles