Triphenylene

Triphenylene
Names
	Preferred IUPAC name Triphenylene
	Other names Benzo[l]phenanthrene; 9,10-Benzophenanthrene; 1,2,3,4-Dibenzonaphthalene; Isochrysene
Identifiers
CAS Number	217-59-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33080 ;
ChEMBL	ChEMBL1797416 ;
ChemSpider	8816 ;
ECHA InfoCard	100.005.385
EC Number	205-922-9;
KEGG	C19541 ;
MeSH	C009590
PubChem CID	9170;
UNII	18WX3373I0 ;
CompTox Dashboard (EPA)	DTXSID9059757 ;
	InChI InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H Key: SLGBZMMZGDRARJ-UHFFFAOYSA-N ; InChI=1/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H;
	SMILES c1(cccc3)c3c(cccc4)c4c2c1cccc2;
Properties
Chemical formula	C18H12
Molar mass	228.294 g·mol−1
Appearance	white solid
Density	1.308 g/cm3
Melting point	198 °C; 388 °F; 471 K
Boiling point	438 °C; 820 °F; 711 K
Magnetic susceptibility (χ)	−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). verify (what is ?) Infobox references

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 D_3h. It is more resonance stable than its isomers chrysene, benz[a]anthracene, 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.