Perylene or perilene is a

polycyclic aromatic hydrocarbon A Polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter— by engine exhaust fumes, tobacco, incine ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

C₂₀H₁₂, occurring as a brown solid. It or its derivatives may be

carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

ic, and it is considered to be a hazardous

pollutant A pollutant or novel entity is a substance or energy introduced into the environment that has undesired effect, or adversely affects the usefulness of a resource. These can be both naturally forming (i.e. minerals or extracted compounds like oi ...

. In

cell membrane The cell membrane (also known as the plasma membrane or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of a cell from the outside environment (the extr ...

cytochemistry Cytochemistry is the branch of cell biology dealing with the detection of cell constituents by means of biochemical analysis and visualization techniques. This is the study of the localization of cellular components through the use of staining met ...

, perylene is used as a

fluorescent Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with color ...

lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...

probe. It is the parent compound of a class of

rylene dye A rylene dye is a dye based on the rylene framework of naphthalene units linked in peri-positions. In homologues additional naphthalene units are added, forming compounds — or ''poly(peri-naphthalene)s'' — such as perylene, terrylene and quart ...

Reactions

Like other polycyclic aromatic compounds, perylene is reduced by alkali metals to give a deeply colored radical anion and a dianion. The

diglyme Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula . It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name '' ...

solvates of these salts have been characterized by

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

Emission

Perylene displays blue

fluorescence Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with colore ...

. It is used as a blue-emitting dopant material in

OLEDs An organic light-emitting diode (OLED), also known as organic electroluminescent (organic EL) diode, is a type of light-emitting diode (LED) in which the emissive electroluminescent layer is an organic compound film that emits light in respons ...

, either pure or substituted. Perylene can also be used as an organic

photoconductor Photoconductivity is an optical and electrical phenomenon in which a material becomes more electrically conductive due to the absorption of electromagnetic radiation such as visible light, ultraviolet light, infrared light, or gamma radiation. W ...

. 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 In chemistry, the molar absorption coefficient or molar attenuation coefficient () is a measurement of how strongly a chemical species absorbs, and thereby attenuates, light at a given wavelength. It is an intrinsic property of the species. The ...

of 38,500 M⁻¹cm⁻¹ at 435.7 nm. Image:Perylene-LongWaveUV.png, Perylene dissolved in

dichloromethane Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with ...

exposed to Long Wave UV radiation Image:Perylene-ShortWaveUV.png, Perylene dissolved in dichloromethane exposed to Short Wave UV radiation

Structure

The perylene

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

consists of two

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms in perylene are sp² hybridized. The structure of perylene has been extensively studied by

Biology

Naturally occurring perylene

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds benzene.html" ;"title="uch as benzene">uch as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with ...

s have been identified in

lichens A lichen ( , ) is a hybrid colony (biology), colony of algae or cyanobacteria living symbiotically among hypha, filaments of multiple fungus species, along with yeasts and bacteria embedded in the cortex or "skin", in a mutualism (biology), m ...

Laurera ''Laurera'' is a genus of fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. The ...

sanguinaria'' Malme and '' Graphis haematites'' Fée. See also

blue amber Blue amber is a rare variety of amber resin that exhibits a blue coloration. Blue amber has been most commonly found in the Dominican Republic—especially in the amber mines around the city of Santiago and, less commonly, in the eastern half of ...

References

{{PAHs IARC Group 3 carcinogens Membrane biology Polycyclic aromatic hydrocarbons Organic semiconductors Fluorescent dyes