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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.
Chemical data
- Formula
- C18H12
- Molecular weight
- 228.3 g/mol
- IUPAC name
- triphenylene
- SMILES
- C1=CC=C2C(=C1)C3=CC=CC=C3C4=CC=CC=C24
- InChIKey
- SLGBZMMZGDRARJ-UHFFFAOYSA-N
- XLogP
- 4.9
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- polycyclic aromatic hydrocarbons
- Has part
- carbon
- 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
via Wikidata · CC0
~7 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “triphenylene” article, available under the CC BY-SA 4.0 licence.