Perylene

Perylene^[1]
Names
	IUPAC name Perylene
	Other names peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene
Identifiers
CAS Number	198-55-0 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.005.365
PubChem CID	9142;
CompTox Dashboard (EPA)	DTXSID4047753 ;
	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−1
Appearance	Brown solid
Melting point	276-279 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

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 435.75 nm (about 6.5 μg is sufficient for absorbence of 1).

Perylene dissolved in dichloromethane exposed to Long Wave UV Light
Perylene dissolved in dichloromethane exposed to Short Wave UV Light

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

^ Perylene at Sigma-Aldrich
^ 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)

[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)

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