Hexaphenylbenzene
Encyclopedia
Hexaphenylbenzene is an aromatic compound composed of a benzene
ring substituted with six phenyl rings.
It may be prepared through a Diels-Alder reaction
by refluxing tetraphenylcyclopentadienone
and diphenylacetylene
in benzophenone
or other high-temperature solvent.
of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. In the crystalline form shown on the left, the molecule forms 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.
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
ring substituted with six phenyl rings.
It may be prepared through a Diels-Alder reaction
Diels-Alder reaction
The Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...
by refluxing tetraphenylcyclopentadienone
Tetraphenylcyclopentadienone
Tetraphenylcyclopentadienone is a dark purple to black crystalline solid at standard temperature and pressure. Because of its highly conjugated nature, this organic compound can be analyzed in the UV spectrum. Tetraphenylcyclopentadienone has a "propeller" shape in its 3D conformation...
and diphenylacetylene
Diphenylacetylene
Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of phenyl groups attached to both ends of an alkyne. It is a colorless crystalline material that is widely used as a building block in organic and as a ligand in organometallic chemistry.-Preparation:Several...
in benzophenone
Benzophenone
Benzophenone is the organic compound with the formula 2CO, generally abbreviated Ph2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.-Uses:...
or other high-temperature solvent.
Structure
Due to steric congestion among the phenyl rings, the stable conformationConformational isomerism
In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted exclusively by rotations about formally single bonds...
of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. In the crystalline form shown on the left, the molecule forms 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.