triphenylene
Sign in to saveAlso known as 9,10-benzophenanthrene, isochrysene
Triphenylene is an organic compound with the formula (C6H4)3. It is a flat polycyclic aromatic hydrocarbon (PAH) that has a highly symmetric and planar structure consists of four fused benzene rings. Triphenylene has delocalized 18-π-electron systems based on a planar structure, corresponding to the symmetry group D3h. It is more resonance stable than its isomers chrysene, [[Benz(a)anthracene|benz[a]anthracene]], [[Benzo(c)phenanthrene|benzo[c]phenanthrene]], and tetracene, hence resists hydrogenation. It is a light yellow powder, insoluble in water.
Wikidata facts
- Mass
- 228.094
Show 4 more facts
- chemical formula
- C₁₈H₁₂
- Commons category
- Triphenylene
- melting point
- 197.0
- canonical SMILES
- C1=CC=C2C(=C1)C3=CC=CC=C3C4=CC=CC=C24
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~7 min read
Article
7 sectionsContents
- Discovery and first synthesis
- Preparation
- Application
- Discotic liquid crystal and organic electronics
- Metal-organic frameworks and covalent organic frameworks
- References
- External links
Triphenylene is an organic compound with the formula (C6H4)3. It is a flat polycyclic aromatic hydrocarbon (PAH) that has a highly symmetric and planar structure consists of four fused benzene rings. Triphenylene has delocalized 18-π-electron systems based on a planar structure, corresponding to the symmetry group D3h. It is more resonance stable than its isomers chrysene, [[Benz(a)anthracene|benz[a]anthracene]], [[Benzo(c)phenanthrene|benzo[c]phenanthrene]], and tetracene, hence resists hydrogenation. It is a light yellow powder, insoluble in water.
Triphenylene serves as a fundamental building block in discotic liquid crystals, where its planar, disc-like structure facilitates the formation of columnar mesophases, enabling applications in organic electronics. It's also being used as the base of covalent and metal organic frameworks.