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Perylene



Perylene
IUPAC name perylene
Identifiers
CAS number 198-55-0
PubChem 9142
SMILES c1ccc5cccc4c5c1c2cccc3cccc4c23
InChI 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
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Perylene or perilene is a polycyclic aromatic hydrocarbon with chemical formula C20H12 and CAS number [198-55-0], 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.

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 434nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10-5 mmol/l). Perylene has a molar extinction coefficient of 38,500 M-1cm-1 at 435.75 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 cause two of the carbons to become sp3 hybridized causing part of the molecule to lose its aromaticity, and therefore its ability to fluoresce. The structure of perylene has been extensively studied by X-ray crystallography.[1]

References

  1. ^ Donaldson, D. M.; Robertson, J. M.; White, J. G. "The crystal and molecular structure of perylene." Proc. R. Soc. Lond. A Math. Phys. Sci. 1953, 220, 311–321. First Page (JSTOR)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Perylene". A list of authors is available in Wikipedia.
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