Tetracyanoquinodimethane

Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula (N≡C−)2C=C6H4=C(−C≡N)2.

TCNQ is prepared by the condensation of 1,4-cyclohexanedione with malononitrile, followed by dehydrogenation of the resulting diene with bromine:[2] The molecule is planar, with D2h symmetry.

[3] Like tetracyanoethylene (TCNE), TCNQ is easily reduced to give a blue-coloured radical anion.

[clarification needed][4] TCNQ achieved great attention because it forms charge-transfer salts with high electrical conductivity.

The complex crystal is an organic semiconductor that exhibits metallic electric conductivity.

Ball-and-stick model of the tetracyanoquinodimethane molecule