Tetracyanoquinodimethane

Tetracyanoquinodimethane (TCNQ) is an organic compound that is widely used in organic chemistry and material science. It is a derivative of quinone and is notable for its ability to accept electrons, which makes it a useful compound in the creation of charge-transfer salts.

Structure and Bonding

TCNQ is a planar molecule related to 7,7,8,8-tetracyanoquinodimethane. The central carbon atoms are sp2 hybridized, and the molecule has a resonance structure that contributes to its electron-accepting ability. The nitrogen atoms are also sp2 hybridized and contribute to the overall polarity of the molecule.

Synthesis

TCNQ can be synthesized from 7,7,8,8-tetracyanoquinodimethane through a process of oxidation and reduction. This process involves the use of copper (II) chloride and sodium borohydride.

Applications

Due to its electron-accepting properties, TCNQ is used in the creation of charge-transfer salts. These salts have applications in organic electronics, including organic field-effect transistors and organic solar cells. TCNQ is also used in the creation of molecular magnets and spintronics devices.

Safety

As with many organic compounds, TCNQ should be handled with care. It can cause irritation to the skin and eyes, and prolonged exposure can lead to more serious health effects. Always use appropriate personal protective equipment when handling TCNQ.

See Also

• Quinone
• Charge-transfer complex
• Organic electronics