Perylene

From Wikipedia, the free encyclopedia
Perylene[1]
Identifiers
CAS number 198-55-0 YesY
PubChem 9142
ChemSpider 8788 N
UNII 5QD5427UN7 N
KEGG C19497 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
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.

Structure

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. When drawing the structure of perylene, it is important not to represent the center ring as a fifth benzene ring. By doing so, this would depict two of the carbons as sp3 hybridized and fail to reflect the aromaticity of part of the molecule, and therefore its ability to fluoresce. 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. 
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