Perylene

Perylene[1]
Names
Preferred IUPAC name
Perylene
Other names
peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.365
KEGG
UNII
Properties
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)
-166.8·10−6 cm3/mol
Hazards
S-phrases (outdated) S22 S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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]

Biology

Naturally occurring perylene quinones have been identified in lichens Laurera sanguinaria Malme and Graphis haematites Fée. [3]

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. Bibcode:1953RSPSA.220..311D. doi:10.1098/rspa.1953.0189. JSTOR 99329.
  3. ↑ Template:Cite journal author = Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich
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