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Perylene - Wikipedia

From Wikipedia, the free encyclopedia

Perylene^[1]

Names

Preferred IUPAC name

Perylene^[2]

Other names

peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene

Identifiers

CAS Number

198-55-0^Y

3D model (JSmol)

Interactive image

Beilstein Reference

1911335

ChEBI

CHEBI:29861^Y

ChEMBL

ChEMBL4296691^N

ChemSpider

8788^Y

ECHA InfoCard

100.005.365

EC Number

205-900-9

Gmelin Reference

104944

KEGG

C19497^Y

PubChem CID

9142

RTECS number

SE3794000

UNII

5QD5427UN7^Y

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^N
Key: CSHWQDPOILHKBI-UHFFFAOYSA-N^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 ^YN ?)

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

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)

v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benz[a]anthracene Benzo[a]fluorene Benzo[c]fluorene Benzo[c]phenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benz[e]acephenanthrylene Benzopyrene Benzo[a]pyrene Benzo[e]pyrene 6H-Benzo[cd]pyrene(Olympicene) Benzo[a]fluoranthene Benzo[b]fluoranthene Benzo[j]fluoranthene Benzo[k]fluoranthene trans-Bicalicene Dibenz[a,h]anthracene Dibenz[a,j]anthracene Pentacene Pentaphene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzo[ghi]perylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene

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