Tricyclobutabenzene

Tricyclobutabenzene is a hydrocarbon with the formula C₁₀H₁₀. It is a derivative of benzene, with three cyclobutane rings fused onto the benzene. Tricyclobutabenzene is a member of the class of compounds known as polycyclic aromatic hydrocarbons (PAHs), which contain multiple aromatic rings.

Structure and Bonding

Tricyclobutabenzene has a unique structure, with three cyclobutane rings fused onto a central benzene ring. This structure results in a molecule that is highly strained, due to the angle strain in the cyclobutane rings and the steric strain from the fusion of the rings onto the benzene. Despite this strain, tricyclobutabenzene is stable enough to be isolated and studied.

Synthesis

Tricyclobutabenzene can be synthesized through a series of organic reactions, starting with benzene. The exact steps of the synthesis can vary, but typically involve the formation of a cycloadduct followed by ring-closing metathesis to form the cyclobutane rings.

Properties

Due to its high strain, tricyclobutabenzene is highly reactive. It undergoes reactions typical of other PAHs, including electrophilic aromatic substitution and oxidation. Tricyclobutabenzene is also notable for its optical properties, which have been studied in detail.

Applications

While tricyclobutabenzene is primarily of interest for its unique structure and reactivity, it has potential applications in materials science and nanotechnology. Its optical properties, in particular, could be useful in the development of new optoelectronic devices.

See also

• Benzene
• Cyclobutane
• Polycyclic aromatic hydrocarbon