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| 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
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| ImageFile2 = Perylene_sample.jpg
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| PIN = Perylene
| OtherNames = ''peri''-Dinaphthalene; Perilene; Dibenz[''de'',''kl'']anthracene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 198-55-0
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| ChEBI_Ref = {{ebicite|
| ChEBI = 29861
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL =
| KEGG_Ref = {{keggcite|changed|kegg}}▼
| ChemSpiderID = 8788▼
| EC_number = 205-900-9
| Gmelin = 104944
| KEGG = C19497
| PubChem = 9142
| UNII_Ref = {{fdacite|changed|FDA}}▼
| RTECS = SE3794000
| UNII = 5QD5427UN7
| SMILES = c1ccc5cccc4c5c1c2cccc3cccc4c23
▲| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
▲| ChemSpiderID = 8788
| 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
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'''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 [[carcinogen]]ic, and it is considered to be a hazardous [[pollutant]]. In [[cell membrane]] [[cytochemistry]], perylene is used as a [[fluorescent]] [[lipid
==
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 [[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<sup>−5</sup> mmol/L). Perylene has a [[molar absorptivity]] of 38,500 M<sup>−1</sup>cm<sup>−1</sup> at 435.7 nm.
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==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 [[Orbital hybridisation|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>
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==Biology==
Naturally occurring perylene
See also [[blue amber]].
==References==
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