Tetracene

Tetracene

0Tetracene, also known as naphthacene, is a polycyclic aromatic hydrocarbon (PAH) consisting of four linearly-fused benzene rings. This yellow crystalline solid is a member of the series of acenes, the parent of which is benzene. Tetracene is a key component in certain organic semiconductors and organic light-emitting diodes (OLEDs).

Structure and Synthesis

Tetracene's structure consists of four benzene rings, sharing a common edge, in a linear arrangement. This structure is responsible for its chemical and physical properties. The synthesis of tetracene involves the Diels-Alder reaction of anthracene with benzyne, a reactive intermediate.

Properties

Tetracene is a yellow crystalline solid at room temperature. It is soluble in common organic solvents and is stable under normal conditions. Its stability is due to the resonance stabilization provided by the four aromatic rings. Tetracene is also characterized by its strong absorbance in the UV-Vis region and its ability to fluoresce.

Applications

Tetracene is used in the manufacture of certain types of organic semiconductors and organic light-emitting diodes (OLEDs). These applications take advantage of tetracene's ability to transport charge and its strong absorbance in the UV-Vis region. In addition, tetracene is used in the preparation of certain dyes and pigments.

Safety

Like other polycyclic aromatic hydrocarbons, tetracene is suspected to be a carcinogen and should be handled with appropriate safety precautions. It is also a potential environmental pollutant and should be disposed of properly.

See Also

• Acene
• Polycyclic aromatic hydrocarbon
• Organic semiconductor
• Organic light-emitting diode