Dithiole

A dithiole is a heterocyclic chemical compound containing a five-membered ring with two sulfur atoms and three carbon atoms. The sulfur atoms are not adjacent. There are two common isomers: 1,2-dithioles and 1,3-dithioles, differentiated by the relative positioning of the sulfur atoms within the ring.

1,2-Dithioles feature the two sulfur atoms in adjacent positions. These compounds can exist in equilibrium with the corresponding dithiolene form, which contains a double bond between the carbon atoms adjacent to the sulfur atoms. 1,2-Dithioles are often associated with redox activity.

1,3-Dithioles have the two sulfur atoms separated by a carbon atom. These are often used as ligands in coordination chemistry. They are also building blocks for tetrathiafulvalene (TTF) derivatives, which are used in organic conductors and superconductors.

The properties and reactivity of dithioles depend significantly on the substituents attached to the carbon atoms of the ring. The presence and nature of these substituents can influence the stability of the ring system, its electronic properties, and its ability to participate in chemical reactions. Dithioles and their derivatives have found applications in various fields including organic electronics, catalysis, and materials science.