terephthalonitrile

Terephthalonitrile, also known as 1,4-dicyanobenzene, is an organic compound with the chemical formula C8H4N2. It is a dinitrile derivative of terephthalic acid. At room temperature, terephthalonitrile exists as a white crystalline solid. It is characterized by two nitrile groups attached to a benzene ring at opposite positions (para substitution).

Terephthalonitrile is primarily used as a monomer in the synthesis of polymers. It is a key precursor for the production of certain high-performance polymers, particularly poly(p-phenylene vinylene) (PPV) derivatives and related conjugated polymers, which find applications in organic electronics such as organic light-emitting diodes (OLEDs) and organic photovoltaics. The nitrile groups can undergo various chemical reactions, allowing for further functionalization and modification of derived materials.

The compound is synthesized through several methods, often involving the dehydration of terephthalamide or the cyanation of 1,4-dihalobenzene. Its reactivity and structural rigidity make it a valuable building block in materials science and organic chemistry research. While not produced in massive industrial quantities compared to some commodity chemicals, it plays a significant role in niche applications requiring specific electronic or structural properties.