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Revision as of 17:58, 8 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 06:49, 29 August 2024 edit undo27.81.39.216 (talk) →Biology: blue amber 
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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 417747847
| Watchedfields = changed
⚫ | Reference=<ref> at ]</ref>
⚫ | verifiedrevid = 417815208
⚫ | Reference = <ref> at ]</ref>
| ImageFileL1 = Perylene.svg | ImageFileL1 = Perylene.svg
| ImageSizeL1 = 120px | ImageSizeL1 = 120px
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| ImageSizeR1 = 150px | ImageSizeR1 = 150px
| ImageFile2 = Perylene_sample.jpg | ImageFile2 = Perylene_sample.jpg
| ImageSize2 = 200px | ImageSize2 =
| PIN = Perylene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| IUPACName = Perylene
| OtherNames = peri-Dinaphthalene; Perilene; Dibenzanthracene | OtherNames = ''peri''-Dinaphthalene; Perilene; Dibenzanthracene
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 198-55-0 | CASNo = 198-55-0
| Beilstein = 1911335
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 29861
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 4296691
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8788
| EC_number = 205-900-9
| Gmelin = 104944
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19497
| PubChem = 9142 | PubChem = 9142
| RTECS = SE3794000
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5QD5427UN7
| SMILES = c1ccc5cccc4c5c1c2cccc3cccc4c23 | SMILES = c1ccc5cccc4c5c1c2cccc3cccc4c23
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI=1/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 | 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CSHWQDPOILHKBI-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=20|H=12 | C=20 | H=12
| Appearance = Brown solid | Appearance = Brown solid
| Density = | Density =
| MeltingPt = 276-279 °C | MeltingPtC = 276 to 279
| MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility =
| MagSus = -166.8·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫ | Section3 = {{Chembox Hazards
}}
⚫ |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| RPhrases =
| SPhrases = {{S22}} {{S24/25}}
}} }}
}} }}
'''Perylene''' or '''perilene''' is a ] with the ] C<sub>20</sub>H<sub>12</sub>, occurring as a brown solid. It or its derivatives may be ]ic, and it is considered to be a hazardous ]. In ] ], perylene is used as a ] ]. It is the parent compound of a class of ]s. '''Perylene''' or '''perilene''' is a ] with the ] C<sub>20</sub>H<sub>12</sub>, occurring as a brown solid. It or its derivatives may be ]ic, and it is considered to be a hazardous ]. In ] ], perylene is used as a ] ] probe. It is the parent compound of a class of ]s.


==Emission== ==Reactions==
Like other polycyclic aromatic compounds, perylene is reduced by alkali metals to give a deeply colored radical anion and a dianion. The ] solvates of these salts have been characterized by ].<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 ]. It is used as a blue-emitting dopant material in ], either pure or substituted. Perylene can be also used as an organic ]. 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 ] of 38,500 M<sup>-1</sup>cm<sup>-1</sup> at 435.75 nm (about 6.5 μg is sufficient for absorbence of 1). Perylene displays blue ]. It is used as a blue-emitting dopant material in ], either pure or substituted. Perylene can be also used as an organic ]. It has an absorption maximum at 434&nbsp;nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10<sup>−5</sup> mmol/L). Perylene has a ] of 38,500&nbsp;M<sup>−1</sup>cm<sup>−1</sup> at 435.7&nbsp;nm.


<gallery> <gallery>
Image:Perylene-LongWaveUV.png|Perylene dissolved in ] exposed to ] Image:Perylene-LongWaveUV.png|Perylene dissolved in ] exposed to ]
Image:Perylene-ShortWaveUV.png|Perylene dissolved in dichloromethane exposed to ] Image:Perylene-ShortWaveUV.png|Perylene dissolved in dichloromethane exposed to ]
</gallery>{{clear-left}} </gallery>{{clear left}}


==Structure== ==Structure==
] typical example of a structure with a perylene core]]
The perylene ] consists of two ] molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the ] atoms in perylene are ] 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 sp<sup>3</sup> 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 ].<ref>{{cite journal | doi = 10.1098/rspa.1953.0189 | author = Donaldson, D. M.; Robertson, J. M.; White, J. G. | title = The crystal and molecular structure of perylene | journal = Proc. R. Soc. Lond. A Math. Phys. Sci. | year = 1953 | volume = 220 | pages = 311–321 | url = http://links.jstor.org/sici?sici=0080-4630(19531208)220%3A1142%3C311%3ATCAMSO%3E2.0.CO%3B2-F First Page (JSTOR) | issue = 1142}}</ref> The perylene ] consists of two ] molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the ] atoms in perylene are ] hybridized. The structure of perylene has been extensively studied by ].<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 = ] | date = 1953 | volume = 220 | pages = 311–321 | issue = 1142 | jstor=99329| bibcode = 1953RSPSA.220..311D | s2cid = 97262226 }}</ref>
{{Clear left}}

==Biology==
Naturally occurring perylene ]s have been identified in ] ''] sanguinaria'' Malme and '']'' Fée. <ref>{{cite journal | author = Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich | title = In situ analysis of a new perylene quinone in lichens by Fourier-transform laser microprobe mass spectrometry with external source | journal=Rapid Communications in Mass Spectrometry| volume = 8 | issue = 1 | pages = 46–52 | date = 1994 | doi=10.1002/rcm.1290080109 | bibcode = 1994RCMS....8...46M }}</ref>
See also ].


==References== ==References==
{{Reflist}}
<references/>


{{PAHs}} {{PAHs}}
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