Picene

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

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464206241

| Reference =Merck Index, 11th Edition, 7368.

| Name = Picene

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

| ImageFile = Picene.svg

| ImageName = Skeletal formula

| ImageFile1 = Picene molecule ball.png

| ImageSize1 = 220px

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

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

| OtherNames = Dibenzo[a,i]phenanthrene
3,4-Benzchrysene
β,β-Binaphthylene ethene

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 8808

| InChI = 1/C22H14/c1-3-7-17-15(5-1)9-11-21-19(17)13-14-20-18-8-4-2-6-16(18)10-12-22(20)21/h1-14H

| InChIKey = GBROPGWFBFCKAG-UHFFFAOYAN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H14/c1-3-7-17-15(5-1)9-11-21-19(17)13-14-20-18-8-4-2-6-16(18)10-12-22(20)21/h1-14H

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GBROPGWFBFCKAG-UHFFFAOYSA-N

| 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}}

| ChEBI = 33090

| SMILES = c5c3c2ccc1ccccc1c2ccc3c4ccccc4c5

}}

|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 pitchy residue obtained in the distillation of peat tar and of petroleum. This is distilled to dryness and the distillate repeatedly recrystallized from cymene. It may be synthetically prepared by the action of anhydrous aluminium chloride on a mixture of naphthalene and 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 intercalated with potassium or rubidium and cooled to below 18 K, picene has been reported to exhibit superconductive properties.{{citation|last=Das|first=Saswato|title= Hydrocarbon Superconductor Discovered |journal=IEEE Spectrum| date=March 2010 |url=https://spectrum.ieee.org/hydrocarbon-superconductor-discovered}} However, due to the apparent inability to reproduce this work,{{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}} the superconducting nature of doped picene has been met with heavy scepticism.{{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}}

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