Perylene: Difference between revisions

| ImageSize2 = 200px

| OtherNames = ''peri''-Dinaphthalene; Perilene; Dibenz[''de'',''kl'']anthracene

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| InChIStdInChI =1 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

| Section2 = {{Chembox Properties

| C=20 | H=12

| MeltingPtMeltingPtC = 276-279 °Cto 279

| Solubility = }}

| AutoignitionAutoignitionPt =

'''Perylene''' or '''perilene''' is a [[polycyclic aromatic hydrocarbon]] with the [[chemical formula]] C₂₀H₁₂, occurring as a brown solid. It or its derivatives may be [[carcinogen]]ic, and it is considered to be a hazardous [[pollutant]]. In [[cell membrane]] [[cytochemistry]], perylene is used as a [[fluorescent]] [[lipid probe]] probe. It is the parent compound of a class of [[rylene dye]]s.

==EmissionReactions==

Perylene displays blue [[fluorescence]]. It is used as a blue-emitting dopant material in [[Organic light-emitting diode|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^-5−5 mmol/L). Perylene has a [[molar absorptivity]] of 38,500  M^-1−1cm^-1−1 at 435.75 7 nm (about 6.5 μg is sufficient for absorbence of 1).

Image:Perylene-LongWaveUV.png|Perylene dissolved in [[dichloromethane]] exposed to [[Ultraviolet|Long Wave UV Lightradiation]]

Image:Perylene-ShortWaveUV.png|Perylene dissolved in dichloromethane exposed to [[Ultraviolet|Short Wave UV Lightradiation]]

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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 [[Orbital hybridisation|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]].<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 = Proc.[[Proceedings R.of Soc.the Lond.Royal Society A Math. Phys. Sci.]] | yeardate = 1953 | volume = 220 | pages = 311–321 | issue = 1142 | jstor=99329| bibcode = 1953RSPSA.220..311D | s2cid = 97262226 }}</ref>