Perylene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Perylene[1]
Perylene.svg Perylene-3D-balls.png
Perylene sample.jpg
Identifiers
CAS number 198-55-0 YesY
PubChem 9142
ChemSpider 8788 N
UNII 5QD5427UN7 N
KEGG C19497 N
ChEBI CHEBI:29861 N
ChEMBL CHEMBL1797415 N
Jmol-3D images Image 1
Properties
Molecular formula C20H12
Molar mass 252.31 g mol−1
Appearance Brown solid
Melting point 276-279 °C
Hazards
S-phrases S22 S24/25
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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.

Structure[edit]

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[edit]

  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.