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Perylene

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Perylene
Names
IUPAC name Perylene
Other names peri-Dinaphthalene; Perilene; Dibenzanthracene
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.005.365 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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
SMILES
  • c1ccc5cccc4c5c1c2cccc3cccc4c23
Properties
Chemical formula C20H12
Molar mass 252.316 g·mol
Appearance Brown solid
Melting point 276-279 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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 mmol/L). Perylene has a molar absorptivity of 38,500 Mcm at 435.75 nm (about 6.5 μg is sufficient for absorbence of 1).

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 sp 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 sp 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.

References

  1. Perylene at Sigma-Aldrich
  2. Donaldson, D. M.; Robertson, J. M.; White, J. G. (1953). First Page (JSTOR) "The crystal and molecular structure of perylene". Proc. R. Soc. Lond. A Math. Phys. Sci. 220 (1142): 311–321. doi:10.1098/rspa.1953.0189. {{cite journal}}: Check |url= value (help)CS1 maint: multiple names: authors list (link)
Polycyclic aromatic hydrocarbons
2 rings
3 rings
4 rings
5 rings
6 rings
7+ rings
General classes
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