Triphenylene is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (C
6H
4)
3. A flat
polycyclic aromatic hydrocarbon
A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
(PAH), it consists of four fused
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
rings. Triphenylene has delocalized 18-''π''-electron systems based on a planar structure, corresponding to the
symmetry group
In group theory, the symmetry group of a geometric object is the group of all transformations under which the object is invariant, endowed with the group operation of composition. Such a transformation is an invertible mapping of the ambient ...
''D''
3h. It is a white or colorless solid.
Preparation
Triphenylene can be isolated from
coal tar
Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoriasi ...
. It is also be synthesized in various ways. One method is
trimerization
In chemistry, a trimer (; ) is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors ofte ...
of
benzyne. Another method involves trapping benzyne with a biphenyl derivative.
Properties
Triphenylene is more
resonance
Resonance describes the phenomenon of increased amplitude that occurs when the frequency of an applied periodic force (or a Fourier component of it) is equal or close to a natural frequency of the system on which it acts. When an oscillatin ...
stable than its isomers
chrysene,
benz nthracene">'a''nthracene,
benzo henanthrene">'c''henanthrene, and
tetracene
Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes.
Tetracene is a molecular organic semiconductor, used in organic ...
. For this reason triphenylene resists
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...
.
As a disc-shaped, planar molecule, triphenylene has attracted attention as the core of discotic
mesogen
A mesogen is a compound that displays liquid crystal properties. Mesogens can be described as disordered solids or ordered liquids because they arise from a unique state of matter that exhibits both solid- and liquid-like properties called the li ...
in
liquid crystal
Liquid crystal (LC) is a state of matter whose properties are between those of conventional liquids and those of solid crystals. For example, a liquid crystal may flow like a liquid, but its molecules may be oriented in a crystal-like way. T ...
line materials.
References
External links
Polycyclic Aromatic Hydrocarbon Structure Index
{{PAHs
Polycyclic aromatic hydrocarbons
Tetracyclic compounds