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
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's 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.

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:33080^N
ChEMBL	ChEMBL1797416^N
ChemSpider	8816^N
ECHA InfoCard	100.005.385
EC Number	205-922-9
KEGG	C19541^Y
MeSH	C009590
PubChem CID	9170
UNII	18WX3373I0^Y
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^N Key: SLGBZMMZGDRARJ-UHFFFAOYSA-N^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
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). N verify (what is ^YN ?) Infobox references