{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 417815208 | Reference = <ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=394475|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Perylene] at Sigma-Aldrich</ref> | ImageFileL1 = Perylene.svg | ImageSizeL1 = 120px | ImageFileR1 = Perylene-3D-balls.png | ImageSizeR1 = 150px | ImageFile2 = Perylene_sample.jpg | ImageSize2 = | PIN = Perylene<ref>{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> | OtherNames = ''peri''-Dinaphthalene; Perilene; Dibenz[''de'',''kl'']anthracene |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 198-55-0 | Beilstein = 1911335 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 29861 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 4296691 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8788 | EC_number = 205-900-9 | Gmelin = 104944 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C19497 | PubChem = 9142 | RTECS = SE3794000 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5QD5427UN7 | SMILES = c1ccc5cccc4c5c1c2cccc3cccc4c23 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CSHWQDPOILHKBI-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=20 | H=12 | Appearance = Brown solid | Density = | MeltingPtC = 276 to 279 | MeltingPt_notes = | BoilingPt = | Solubility = | MagSus = −166.8·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Perylene''' or '''perilene''' is a polycyclic aromatic hydrocarbon with the chemical formula C<sub>20</sub>H<sub>12</sub>, 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.<ref>{{cite journal |doi=10.1021/om970610g|title=Solvent-Shared and Solvent-Separated Ion Multiples of Perylene Radical Anions and Dianions: An Exemplary Case of Alkali Metal Cation Solvation|year=1998|last1=Näther|first1=Christian|last2=Bock|first2=Hans|last3=Havlas|first3=Zdenek|last4=Hauck|first4=Tim|journal=Organometallics|volume=17|issue=21|pages=4707–4715}}</ref>

==Emission== Perylene displays blue fluorescence. It is used as a blue-emitting dopant material in OLEDs, either pure or substituted. Perylene can also be used as an organic photoconductor. It has an absorption maximum at 434&nbsp;nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 × 10<sup>−5</sup> mmol/L). Perylene has a molar absorptivity of 38,500&nbsp;M<sup>−1</sup>cm<sup>−1</sup> at 435.7&nbsp;nm.

<gallery> Image:Perylene-LongWaveUV.png|Perylene dissolved in dichloromethane exposed to Long Wave UV radiation Image:Perylene-ShortWaveUV.png|Perylene dissolved in dichloromethane exposed to Short Wave UV radiation </gallery>{{clear left}}

==Structure== [[File:Vat Red 29.png|thumbnail|300px|left|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 sp<sup>2</sup> hybridized. The structure of perylene has been extensively studied by X-ray crystallography.<ref>{{cite journal | doi = 10.1098/rspa.1953.0189 | author = Donaldson, D. M. | author2 = Robertson, J. M. | author3 = White, J. G. | title = The crystal and molecular structure of perylene | journal = Proceedings of the Royal Society A | date = 1953 | volume = 220 | pages = 311–321 | issue = 1142 | jstor=99329| bibcode = 1953RSPSA.220..311D | s2cid = 97262226 }}</ref> {{Clear left}}

==Biology== Naturally occurring perylene quinones have been identified in lichens ''Laurera sanguinaria'' Malme and ''Graphis haematites'' Fée. <ref>{{cite journal | author = Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich | title = In situ analysis of a new perylene quinone in lichens by Fourier-transform laser microprobe mass spectrometry with external source | journal=Rapid Communications in Mass Spectrometry| volume = 8 | issue = 1 | pages = 46–52 | date = 1994 | doi=10.1002/rcm.1290080109 | bibcode = 1994RCMS....8...46M }}</ref> See also blue amber.

==References== {{Reflist}}

{{PAHs}}

Category:IARC Group 3 carcinogens Category:Membrane biology Category:Polycyclic aromatic hydrocarbons Category:Organic semiconductors Category:Fluorescent dyes