Triphenylene

Triphenylene is a hydrocarbon with the formula C₁₄H₁₀. It is a flat polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. Triphenylene can be isolated from coal tar, but it is also obtained in the laboratory by dehydrogenation of phenanthrene.

Structure and properties

Triphenylene is a disc-shaped molecule, which makes it a potential candidate for the development of organic semiconductor materials. It is also a starting material for the synthesis of other PAHs. The compound is soluble in common organic solvents. It sublimes when heated. Triphenylene is a colorless solid that crystallizes in platelets.

Synthesis

Triphenylene can be synthesized by various methods. The classic method is by dehydrogenation of phenanthrene. Another method is the Diels-Alder reaction of anthracene with maleic anhydride in the presence of aluminium chloride, followed by dehydration of the resulting ketone.

Applications

Triphenylene has been used as a building block in the synthesis of larger PAHs. It is also used in the preparation of certain dyes and pigments. In addition, it has potential applications in organic electronics due to its semiconducting properties.

Safety

Like other PAHs, triphenylene is potentially hazardous to health. It is not classified as a human carcinogen, but it may be harmful if inhaled, ingested, or in contact with the skin. Proper safety precautions should be taken when handling this compound.

See also

• Phenanthrene
• Anthracene
• Polycyclic aromatic hydrocarbon