Perylene

Perylene^[1]

Names
IUPAC name Perylene
Other names peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene
Identifiers
CAS Number	198-55-0
ChEBI	CHEBI:29861
ChEMBL	ChEMBL1797415
ChemSpider	8788
Jmol interactive 3D	Image
KEGG	C19497
PubChem	9142
UNII	5QD5427UN7
InChI InChI=1S/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H Key: CSHWQDPOILHKBI-UHFFFAOYSA-N InChI=1/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H Key: CSHWQDPOILHKBI-UHFFFAOYAD
SMILES c1ccc5cccc4c5c1c2cccc3cccc4c23
Properties
Chemical formula	C20H12
Molar mass	252.32 g·mol^−1
Appearance	Brown solid
Melting point	276 to 279 °C (529 to 534 °F; 549 to 552 K)
Hazards
S-phrases	S22 S24/25
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

Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C₂₀H₁₂, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe. It is the parent compound of a class of rylene dyes.

Emission

Perylene displays blue fluorescence. It is used as a blue-emitting dopant material in OLEDs, either pure or substituted. Perylene can be also used as an organic photoconductor. It has an absorption maximum at 434 nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10⁻⁵ mmol/L). Perylene has a molar absorptivity of 38,500 M⁻¹cm⁻¹ at 435.7 nm.

• 

  Perylene dissolved in dichloromethane exposed to Long Wave UV radiation

• 

  Perylene dissolved in dichloromethane exposed to Short Wave UV radiation

Structure

Vat Red 29 typical example of a structure with a perylene core

The perylene molecule consists of two naphthalene molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the carbon atoms in perylene are sp² hybridized. The structure of perylene has been extensively studied by X-ray crystallography.^[2]

References

1. Perylene at Sigma-Aldrich
2. Donaldson, D. M.; Robertson, J. M.; White, J. G. (1953). "The crystal and molecular structure of perylene". Proceedings of the Royal Society A 220 (1142): 311–321. doi:10.1098/rspa.1953.0189. JSTOR 99329.