Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pyrene: Difference between pages
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Saving copy of the {{chembox}} taken from revid 457372542 of page Pyrene for the Chem/Drugbox validation project (updated: ''). |
Alfa-ketosav (talk | contribs) there, the numbers are close to the atoms but not on their site |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Pyrene|oldid=457372542}} 457372542] of page [[Pyrene]] with values updated to verified values.}} |
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{{other uses}} |
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{{chembox |
{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 464376838 |
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| Name = Pyrene |
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| ImageFile = Pyrene.svg |
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| ImageSize = 190px |
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| ImageAlt = Structural formula of pyrene |
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| ImageFile1 = Pyrene-3D-balls.png |
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| ImageFile1 = Pyrene molecule from xtal ball.png |
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| ImageSize1 = 190px |
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| ImageSize1 = 200px |
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| ImageAlt1 = Ball-and-stick model of the pyrene molecule |
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| OtherNames = benzo[def]phenanthrene |
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| ImageFile2 = Pyrene crystal 1.jpg |
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| Section1 = {{Chembox Identifiers |
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| PIN = Pyrene<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| OtherNames = Benzo[''def'']phenanthrene |
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| Section1 = {{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 39106 |
| ChEBI = 39106 |
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| SMILES = |
| SMILES = c1cc2cccc3c2c4c1cccc4cc3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 29153 |
| ChemSpiderID = 29153 |
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| PubChem = 31423 |
| PubChem = 31423 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 129-00-0 |
| CASNo = 129-00-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = UR2450000 |
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| UNII = 9E0T7WFW93 |
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| RTECS = UR2450000 |
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| Beilstein = 1307225 |
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| Gmelin = 84203 |
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}} |
}} |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=16 | H=10 |
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| Formula = {{carbon}}<sub>16</sub>{{hydrogen}}<sub>10</sub> |
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| Appearance = colorless solid |
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| MolarMass = 202.25 g/mol |
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| Appearance = colorless solid |
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(yellow impurities are often found at trace levels in many samples). |
(yellow impurities are often found at trace levels in many samples). |
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| Density = 1.271 g/cm<sup>3</sup><ref name=crc>Haynes, p. 3.472</ref> |
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| Solubility = 0.049 mg/L (0 °C)<br>0.139 mg/L (25 °C)<br>2.31 mg/L (75 °C)<ref>Haynes, p. 5.162</ref> |
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| Solubility = 0.135 mg/l |
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| MeltingPtC = 150.62 |
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| MeltingPt = 145-148 °C (418-421 K) |
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| MeltingPt_ref = <ref name=crc/> |
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| BoilingPt = 404 °C (677 K) |
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| BoilingPtC = 394 |
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| BoilingPt_ref = <ref name=crc/> |
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| MagSus = -147·10<sup>−6</sup> cm<sup>3</sup>/mol<ref>Haynes, p. 3.579</ref> |
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| LogP = 5.08<ref>Haynes, p. 5.176</ref> |
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| BandGap = 2.02 eV<ref>Haynes, p. 12.96</ref> |
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}} |
}} |
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| Section3 = {{Chembox Structure |
| Section3 = {{Chembox Structure |
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| Structure_ref=<ref>{{cite journal|doi=10.1107/S0365110X65001494 |title=The crystal and molecular structure of pyrene |date=1965 |last1=Camerman |first1=A. |last2=Trotter |first2=J. |journal=Acta Crystallographica |volume=18 |issue=4 |pages=636–643 |doi-access=free }}</ref> |
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| CrystalStruct = |
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| CrystalStruct = [[Monoclinic]] |
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| Dipole = |
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| SpaceGroup = P2<sub>1</sub>/a |
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| PointGroup = |
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| LattConst_a = 13.64 Å |
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| LattConst_b = 9.25 Å |
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| LattConst_c = 8.47 Å |
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| LattConst_alpha = |
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| LattConst_beta = 100.28 |
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| LattConst_gamma = |
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| LattConst_ref = |
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| LattConst_Comment = |
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| UnitCellVolume = |
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| UnitCellFormulas = 4 |
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}} |
}} |
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| Section4 = {{Chembox Thermochemistry |
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| Thermochemistry_ref=<ref>Haynes, pp. 5.34, 6.161</ref> |
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| ExternalMSDS = |
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| HeatCapacity = 229.7 J/(K·mol) |
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| MainHazards = irritant |
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| Entropy = 224.9 J·mol<sup>−1</sup>·K<sup>−1</sup> |
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| NFPA-H = 2 |
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| DeltaHf = 125.5 kJ·mol<sup>−1</sup> |
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| NFPA-F = 1 |
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| DeltaHfus = 17.36 kJ·mol<sup>−1</sup> |
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| NFPA-R = |
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}} |
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| FlashPt = non-flammable |
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| Section7 = {{Chembox Hazards |
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| RPhrases = 36/37/38-45-53 |
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| ExternalSDS = |
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| SPhrases = 24/25-26-36 |
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| MainHazards = irritant |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{HPhrases|H315 |H319 |H335 |H410 }} |
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| PPhrases = {{PPhrases|P261, |P264, |P271, |P273, |P280, |P302+P352, |P304+P340, |P305+P351+P338, |P312, |P321, |P332+P313, |P337+P313, |P362, |P391, |P403+P233, |P405|P501}} |
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| GHS_ref =<ref>GHS: [https://pubchem.ncbi.nlm.nih.gov/compound/31423 PubChem]</ref> |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| FlashPt = non-flammable |
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}} |
}} |
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| Section8 = {{Chembox Related |
| Section8 = {{Chembox Related |
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| OtherFunction_label = PAHs |
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| OtherFunction = [[benzopyrene]] |
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}} |
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}} |
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'''Pyrene''' is a [[polycyclic aromatic hydrocarbon]] (PAH) consisting of four fused [[benzene]] rings, resulting in a flat [[Aromaticity|aromatic]] system. The chemical formula is {{chem2|C16H10}}. This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during [[Combustion#Incomplete|incomplete combustion]] of organic compounds.<ref>{{cite journal |doi=10.1021/cr100428a|title=Pyrene-Based Materials for Organic Electronics|year=2011|last1=Figueira-Duarte|first1=Teresa M.|last2=Müllen|first2=Klaus|journal=Chemical Reviews|volume=111|issue=11|pages=7260–7314|pmid=21740071}}</ref> |
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==Occurrence and properties== |
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Pyrene was first isolated from [[coal tar]], where it occurs up to 2% by weight. As a peri-fused PAH, pyrene is much more [[Resonance (chemistry)|resonance-stabilized]] than its five-member-ring containing isomer [[fluoranthene]]. Therefore, it is produced in a wide range of combustion conditions. For example, automobiles produce about 1 μg/km.<ref name=Ullmann>Senkan, Selim and Castaldi, Marco (2003) "Combustion" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim.</ref> |
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===Reactions=== |
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Oxidation with [[Chromate ion|chromate]] affords perinaphthenone and then naphthalene-1,4,5,8-tetracarboxylic acid. Pyrene undergoes a series of [[hydrogenation]] reactions and is susceptible to halogenation, [[Diels-Alder]] additions, and nitration, all with varying degrees of selectivity.<ref name=Ullmann/> Bromination occurs at one of the 3-positions.<ref>{{cite journal | last1 = Gumprecht | first1 = W. H. | year = 1968 | title = 3-Bromopyrene | journal = Org. Synth. | volume = 48 | page = 30 | doi = 10.15227/orgsyn.048.0030 }}</ref> |
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Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared.<ref>{{cite journal |doi=10.1107/S2053229614015290|title=Bis(pyrene)metal complexes of vanadium, niobium and titanium: Isolable homoleptic pyrene complexes of transition metals|year=2014|last1=Kucera|first1=Benjamin E.|last2=Jilek|first2=Robert E.|last3=Brennessel|first3=William W.|last4=Ellis|first4=John E.|journal=Acta Crystallographica Section C: Structural Chemistry|volume=70|issue=8|pages=749–753|pmid=25093352}}</ref> |
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===Photophysics=== |
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Pyrene and its derivatives are used commercially to make [[dye]]s and dye precursors, for example [[pyranine]] and naphthalene-1,4,5,8-tetracarboxylic acid. It has strong absorbance in UV-Vis in three sharp bands at 330 nm in DCM. The emission is close to the absorption, but moving at 375 nm.<ref name=":0">{{Cite journal|last1=Tagmatarchis|first1=Nikos|last2=Ewels|first2=Christopher P.|last3=Bittencourt|first3=Carla|last4=Arenal|first4=Raul|last5=Pelaez-Fernandez|first5=Mario|last6=Sayed-Ahmad-Baraza|first6=Yuman|last7=Canton-Vitoria|first7=Ruben|date=2017-06-05|title=Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion|journal=npj 2D Materials and Applications|language=en|volume=1|issue=1|pages=13|doi=10.1038/s41699-017-0012-8|issn=2397-7132|doi-access=free}}</ref> The morphology of the signals change with the solvent. Its derivatives are also valuable molecular probes via [[fluorescence]] spectroscopy, having a high quantum yield and lifetime (0.65 and 410 nanoseconds, respectively, in [[ethanol]] at 293 K). Pyrene was the first molecule for which [[excimer]] behavior was discovered.<ref>{{cite journal |last1=Van Dyke |first1=David A. |last2=Pryor |first2=Brian A. |last3=Smith |first3=Philip G. |last4=Topp |first4=Michael R. |title=Nanosecond Time-Resolved Fluorescence Spectroscopy in the Physical Chemistry Laboratory: Formation of the Pyrene Excimer in Solution |journal=Journal of Chemical Education |date=May 1998 |volume=75 |issue=5 |pages=615 |doi=10.1021/ed075p615|bibcode=1998JChEd..75..615V }}</ref> Such excimer appears around 450 nm. [[Theodor Förster]] reported this in 1954.<ref>{{cite journal |last1=Förster |first1=Th. |last2=Kasper |first2=K. |title=Ein Konzentrationsumschlag der Fluoreszenz. |journal=Zeitschrift für Physikalische Chemie |date=June 1954 |volume=1 |issue=5_6 |pages=275–277 |doi=10.1524/zpch.1954.1.5_6.275}}</ref> |
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==Applications== |
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{{multiple image |
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| align = left |
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| direction = vertical |
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| width = 180 |
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| image1 = Br4Py self-assembly on Au.jpg |
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| caption1 = |
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| image2 = Br4Py self-assembly on Au 2.jpg |
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| caption2 = [[Scanning tunneling microscopy|STM]] image of self-assembled Br<sub>4</sub>Py molecules on Au(111) surface (top) and its model (bottom; pink spheres are Br atoms).<ref>{{cite journal|doi=10.1039/C4CC02753A |title=Self-assembly of pyrene derivatives on Au(111): Substituent effects on intermolecular interactions |journal=Chem. Commun. |volume=50 |issue=91 |pages=14089–92 |year=2014 |last1=Pham |first1=Tuan Anh |last2=Song |first2=Fei |last3=Nguyen |first3=Manh-Thuong |last4=Stöhr |first4=Meike |pmid=24905327 |doi-access=free }}</ref> |
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}} |
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Pyrene's fluorescence [[emission spectrum]] is very sensitive to solvent polarity, so pyrene has been used as a probe to determine solvent environments. This is due to its excited state having a different, non-planar structure than the ground state. Certain emission bands are unaffected, but others vary in intensity due to the strength of interaction with a solvent.[[File:Pyrene-numbering.svg|thumb|190px|Diagram showing the numbering and ring fusion locations of pyrene according to [[IUPAC nomenclature of organic chemistry]].]] |
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Pyrenes are strong electron donor materials and can be combined with several materials in order to make electron donor-acceptor systems which can be used in energy conversion and light harvesting applications.<ref name=":0" /> |
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==Safety and environmental factors== |
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Although it is not as problematic as [[benzopyrene]], [[animal studies]] have shown pyrene is [[toxic]] to the [[kidneys]] and [[liver]]. It is now known that pyrene affects several living functions in fish and algae.<ref>{{Cite journal|last1=Oliveira|first1=M.|last2=Ribeiro|first2=A.|last3=Hylland|first3=K.|last4=Guilhermino|first4=L.|title=Single and combined effects of microplastics and pyrene on juveniles (0+ group) of the common goby Pomatoschistus microps (Teleostei, Gobiidae)|journal=Ecological Indicators|volume=34|pages=641–647|doi=10.1016/j.ecolind.2013.06.019|year=2013}}</ref><ref>{{Cite journal|last1=Oliveira|first1=M.|last2=Gravato|first2=C.|last3=Guilhermino|first3=L.|title=Acute toxic effects of pyrene on Pomatoschistus microps (Teleostei, Gobiidae): Mortality, biomarkers and swimming performance|journal=Ecological Indicators|volume=19|pages=206–214|doi=10.1016/j.ecolind.2011.08.006|year=2012}}</ref><ref>{{Cite journal|last1=Oliveira|first1=M.|last2=Ribeiro|first2=A.|last3=Guilhermino|first3=L.|title=Effects of exposure to microplastics and PAHs on microalgae Rhodomonas baltica and Tetraselmis chuii|journal=Comparative Biochemistry and Physiology Part A: Molecular & Integrative Physiology|volume=163|pages=S19–S20|doi=10.1016/j.cbpa.2012.05.062|year=2012}}</ref><ref>{{Cite journal|last1=Oliveira|first1=M.|last2=Ribeiro|first2=A.|last3=Guilhermino|first3=L.|title=Effects of short-term exposure to microplastics and pyrene on Pomatoschistus microps (Teleostei, Gobiidae)|journal=Comparative Biochemistry and Physiology Part A: Molecular & Integrative Physiology|volume=163|pages=S20|doi=10.1016/j.cbpa.2012.05.063|year=2012}}</ref> |
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Its biodegradation has been heavily examined. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.<ref>{{cite journal |doi=10.3390/ijerph6010278|doi-access=free|title=Bacterial Degradation of Aromatic Compounds|year=2009|last1=Seo|first1=Jong-Su|last2=Keum|first2=Young-Soo|last3=Li|first3=Qing|journal=International Journal of Environmental Research and Public Health|volume=6|issue=1|pages=278–309|pmid=19440284|pmc=2672333}}</ref> Experiments in pigs show that urinary [[1-hydroxypyrene]] is a metabolite of pyrene, when given orally.<ref>{{cite journal|doi=10.3109/00498258309052279|pmid=6659544|title=Identification of 1-hydroxypyrene as a major metabolite of pyrene in pig urine|journal=Xenobiotica|volume=13|issue=7|pages=415–20|year=1983|last1=Keimig|first1=S. D.|last2=Kirby|first2=K. W.|last3=Morgan|first3=D. P.|last4=Keiser|first4=J. E.|last5=Hubert|first5=T. D.}}</ref> |
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==See also== |
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* [[List of interstellar and circumstellar molecules]] |
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* [[Perhydropyrene]] |
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==References== |
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{{Reflist}} |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293}} |
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==Further reading== |
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* {{cite book | last = Birks | first = J. B. | title = Photophysics of Aromatic Molecules | location = London | publisher = Wiley | year = 1969 }} |
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* {{cite book | last = Valeur | first = B. | title = Molecular Fluorescence: Principles and Applications | location = New York | publisher = Wiley-VCH | year = 2002 }} |
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* {{cite journal |last1=Birks |first1=J. B. |title=Excimers |journal=Reports on Progress in Physics |date=1975 |volume=38 |issue=8 |pages=903–974 |doi=10.1088/0034-4885/38/8/001 |bibcode=1975RPPh...38..903B |s2cid=240065177 |language=en |issn=0034-4885}} |
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* {{cite book | last = Fetzer | first = J. C. | title = The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons | location = New York | publisher = Wiley | year = 2000 }} |
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{{Hydrocarbons}} |
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{{PAHs}} |
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{{Molecules detected in outer space}} |
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{{Authority control}} |
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[[Category:Pyrenes]] |
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[[Category:Polycyclic aromatic hydrocarbons]] |
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[[Category:PBT substances]] |