Hexaphenylbenzene is an aromatic compound composed of a benzene ring substituted with six phenyl rings. It is a colorless solid. The compound is the parent member of a wider class of hexaarylbenzenes, which are mainly of theoretical interest.
Preparation It is prepared by heating tetraphenylcyclopentadienone and diphenylacetylene in benzophenone or other high-temperature solvent. The reaction proceeds via a Diels–Alder reaction to give the hexaphenyldienone, which then eliminates carbon monoxide.
Together with 1,2,3,4-tetraphenylnaphthalene, hexaphenylbenzene forms by the chromium-catalyzed oligomerization of diphenylacetylene. It may also be prepared by the dicobalt octacarbonyl-catalyzed alkyne trimerisation of diphenylacetylene.
Structure
The stable conformation of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the phenyl rings are rotated about 65°, while in the gas phase, they are perpendicular with some slight oscillations.
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![Hexaphenylbenzene: Perspective view of the crystal structure of hexaphenylbenzene, showing the rotation of the phenyl rings. Hydrogen atoms have been omitted for clarity.[4]](https://upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Hexaphenylbenzene_xtal_perspective.png/500px-Hexaphenylbenzene_xtal_perspective.png?utm_source=en.wikipedia.org&utm_campaign=parser&utm_content=thumbnail)
