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 Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include s ...

. 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 quar ...

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.

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. Image:Perylene-LongWaveUV.png, Perylene dissolved in

dichloromethane Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour 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 consists of two

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

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.

Biology

Naturally occurring perylene

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds

uch as benzene or naphthalene Uch ( pa, ; ur, ), frequently referred to as Uch Sharīf ( pa, ; ur, ; ''"Noble Uch"''), is a historic city in the southern part of Pakistan's Punjab province. Uch may have been founded as Alexandria on the Indus, a town founded by Alexand ...

by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double ...

s have been identified in lichens ''

Laurera ''Laurera'' is a genus of fungi within the Trypetheliaceae family. Species It was known to have nearly 50 species at one point in time, but most have these have become synonyms for other species, within the '' Astrothelium'' and ''Bathelium'' g ...

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

References

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