Perylene

Perylene^[1]
Names
	Preferred IUPAC name Perylene
	Other names peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene
Identifiers
CAS Number	198-55-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1911335
ChEBI	CHEBI:29861 ;
ChEMBL	ChEMBL4296691 ;
ChemSpider	8788 ;
ECHA InfoCard	100.005.365
EC Number	205-900-9;
Gmelin Reference	104944
KEGG	C19497 ;
PubChem CID	9142;
RTECS number	SE3794000;
UNII	5QD5427UN7 ;
CompTox Dashboard (EPA)	DTXSID4047753 ;
	InChI InChI=1S/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 Key: CSHWQDPOILHKBI-UHFFFAOYSA-N ;
	SMILES c1ccc5cccc4c5c1c2cccc3cccc4c23;
Properties
Chemical formula	C20H12
Molar mass	252.316 g·mol−1
Appearance	Brown solid
Melting point	276 to 279 °C (529 to 534 °F; 549 to 552 K)
Magnetic susceptibility (χ)	-166.8·10−6 cm3/mol
	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. It is the parent compound of a class of rylene dyes.

Reactions

Like other polycyclic aromatic compounds, perylene is reduced by alkali metals to give a deeply colored radical anion and a dianion. The diglyme solvates of these salts have been characterized by X-ray crystallography.^[3]

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.

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

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.^[4]

Biology

Naturally occurring perylene quinones have been identified in lichens Laurera sanguinaria Malme and Graphis haematites Fée. ^[5] See also blue amber.

References

^ Perylene at Sigma-Aldrich
^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Näther, Christian; Bock, Hans; Havlas, Zdenek; Hauck, Tim (1998). "Solvent-Shared and Solvent-Separated Ion Multiples of Perylene Radical Anions and Dianions: An Exemplary Case of Alkali Metal Cation Solvation". Organometallics. 17 (21): 4707–4715. doi:10.1021/om970610g.
^ 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. S2CID 97262226.
^ Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich (1994). "In situ analysis of a new perylene quinone in lichens by Fourier-transform laser microprobe mass spectrometry with external source". Rapid Communications in Mass Spectrometry. 8 (1): 46–52. Bibcode:1994RCMS....8...46M. doi:10.1002/rcm.1290080109.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1] Perylene at Sigma-Aldrich

[2] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[3] Näther, Christian; Bock, Hans; Havlas, Zdenek; Hauck, Tim (1998). "Solvent-Shared and Solvent-Separated Ion Multiples of Perylene Radical Anions and Dianions: An Exemplary Case of Alkali Metal Cation Solvation". Organometallics. 17 (21): 4707–4715. doi:10.1021/om970610g.

[4] 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. S2CID 97262226.

[5] Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich (1994). "In situ analysis of a new perylene quinone in lichens by Fourier-transform laser microprobe mass spectrometry with external source". Rapid Communications in Mass Spectrometry. 8 (1): 46–52. Bibcode:1994RCMS....8...46M. doi:10.1002/rcm.1290080109.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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