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Chemical compound From Wikipedia, the free encyclopedia
Triphenylene is an organic compound with the formula (C6H4)3. A flat polycyclic aromatic hydrocarbon (PAH), it 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 a white or colorless solid.
Names | |
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Preferred IUPAC name
Triphenylene[1] | |
Other names
Benzo[l]phenanthrene 9,10-Benzophenanthrene 1,2,3,4-Dibenzonaphthalene Isochrysene | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.385 |
EC Number |
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KEGG | |
MeSH | C009590 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C18H12 | |
Molar mass | 228.294 g·mol−1 |
Appearance | white |
Density | 1.308 g/cm3[2] |
Melting point | 198 °C; 388 °F; 471 K |
Boiling point | 438 °C; 820 °F; 711 K |
-156.6·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triphenylene can be isolated from coal tar. It can also be synthesized in various ways. One method is trimerization of benzyne.[3] Another method involves trapping benzyne with a biphenyl derivative.[4]
Triphenylene is more resonance stable than its isomers chrysene, benz[a]anthracene, benzo[c]phenanthrene, and tetracene. For this reason triphenylene resists hydrogenation.[5]
As a disc-shaped, planar molecule, triphenylene has attracted attention as the core of discotic mesogen in liquid crystalline materials.[6]
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