tetrakyanoetyleeni

Tetrakyanoetyleeni, often abbreviated as TCNE, is an organic compound with the chemical formula C6N4. It is a pale yellow crystalline solid that is known for its electron-accepting properties. TCNE is a highly symmetrical molecule, featuring a central ethylene core surrounded by four cyanide groups. This unique structure contributes to its strong electron affinity.

TCNE is synthesized through various methods, with a common route involving the reaction of malononitrile with bromine. The compound is relatively stable but can react with strong oxidizing agents. Its most notable characteristic is its ability to form charge-transfer complexes with electron-donating molecules. These complexes can exhibit interesting electrical and optical properties, leading to applications in areas like organic conductors and semiconductors.

Due to its electron-accepting nature, TCNE is also used as a reagent in organic synthesis. It can participate in cycloaddition reactions and act as an oxidant in certain transformations. While not as widely produced as some industrial chemicals, TCNE holds significance in research laboratories for its distinctive chemical behavior and potential in materials science. Its handling requires care due to its potential toxicity.