Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Picene: Difference between pages

{{other uses|Picene (disambiguation)|Piceno (disambiguation)}}

| Watchedfields = changed

| verifiedrevid = 464206241

| Reference =<ref>''[[Merck Index]]'', 11th Edition, '''7368'''.</ref>

| Name = Picene

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Skeletal formula

| ImageFile1 = Picene molecule ball.png

| ImageSize1 = 220px

| ImageAlt1 = Ball-and-stick model of the picene molecule ball

| PIN = Picene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 206 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>

| OtherNames = Dibenzo[''a'',''i'']phenanthrene<br />3,4-Benzchrysene<br />β,β-Binaphthylene ethene

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| Beilstein = 1912414

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19500

| PubChem = 9162

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 213-46-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = F70R8ZBR7T

| ChEBI_Ref = {{ebicite|correct|EBI}}

|Section2={{Chembox Properties

| Formula = C₂₂H₁₄

| MolarMass = 278.33 g/mol

| Density = ? g/cm³

| MeltingPtC = 366 to 367

| MeltingPt_notes =

| BoilingPtC = 518 to 520

| BoilingPt_notes =

|Section7 = {{Chembox Hazards

| GHSPictograms = {{GHS08}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|371}}

| PPhrases = {{P-phrases|260|264|270|309+311|405|501}}

}}

'''Picene''' is a [[hydrocarbon]] found in the [[Pitch (resin)|pitch]]y residue obtained in the [[distillation]] of [[peat]] [[tar]] and of [[petroleum]]. This is distilled to dryness and the [[distillate]] repeatedly [[Recrystallization (chemistry)|recrystallize]]d from [[cymene]]. It may be synthetically prepared by the action of [[anhydrous]] [[aluminium chloride]] on a mixture of [[naphthalene]] and [[1,2-Dibromoethane|1,2-dibromoethane]], or by distilling a-dinaphthostilbene. It crystallizes in large colorless plates which possess a blue [[fluorescence]]. It is soluble in concentrated [[sulfuric acid]] with a green color. [[Chromic acid]] in [[glacial acetic acid]] solution oxidizes it to picene-[[quinone]], picene-quinone [[carboxylic acid]], and finally to [[phthalic acid]].

When [[Intercalation (chemistry)|intercalated]] with [[potassium]] or [[rubidium]] and cooled to below 18 K, picene has been reported to exhibit superconductive properties.<ref>{{citation|last=Das|first=Saswato|title= Hydrocarbon Superconductor Discovered |journal=[[IEEE Spectrum]]| date=March 2010 |url=https://spectrum.ieee.org/hydrocarbon-superconductor-discovered}}</ref> However, due to the apparent inability to reproduce this work,<ref>{{citation|last=Artioli|first=Gianluca A.|first2=Lorenzo|last2=Malavasi|title= Superconductivity in metal-intercalated aromatic hydrocarbons |journal=[[J. Mater. Chem. C]]| date=Dec 2013 |volume=2|issue=9|pages=1577|doi=10.1039/C3TC32326A}}</ref> the superconducting nature of doped picene has been met with heavy scepticism.<ref>{{citation|last=Heguri|first=Satoshi|first2=Mototada|last2=Kobayashi|first3=Katsumi|last3=Tanigaki|title= Questioning the existence of superconducting potassium doped phases for aromatic hydrocarbons |journal=[[Phys. Rev. B]]| date=May 2015 |volume=92|issue=1|pages=014502|doi=10.1103/PhysRevB.92.014502|bibcode=2015PhRvB..92a4502H}}</ref>

Picene is also a major constituent of the hydrocarbon mineral [[idrialite]].

==See also==

* [[Olympicene]], which has the same number of rings linked in a different way

==References==

<references/>

{{1911|wstitle=Picene|volume=21|page=581}}

{{PAHs}}

[[Category:Polycyclic aromatic hydrocarbons]]