Picene

Picene^[1]
	Skeletal formula
Names
	Preferred IUPAC name Picene
	Other names Dibenzo[a,i]phenanthrene; 3,4-Benzchrysene; β,β-Binaphthylene ethene
Identifiers
CAS Number	213-46-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1912414
ChEBI	CHEBI:33090 ;
ChemSpider	8808 ;
ECHA InfoCard	100.005.381
KEGG	C19500 ;
PubChem CID	9162;
UNII	F70R8ZBR7T ;
CompTox Dashboard (EPA)	DTXSID8073895 ;
	InChI InChI=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 Key: GBROPGWFBFCKAG-UHFFFAOYSA-N ; 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 Key: GBROPGWFBFCKAG-UHFFFAOYAN;
	SMILES c5c3c2ccc1ccccc1c2ccc3c4ccccc4c5;
Properties
Chemical formula	C22H14
Molar mass	278.33 g/mol
Density	? g/cm3
Melting point	366 to 367 °C (691 to 693 °F; 639 to 640 K)
Boiling point	518 to 520 °C (964 to 968 °F; 791 to 793 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H371
Precautionary statements	P260, P264, P270, P309+P311, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[3] However, due to the apparent inability to reproduce this work,^[4] the superconducting nature of doped picene has been met with heavy scepticism.^[5]

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

References

^ Merck Index, 11th Edition, 7368.
^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 206. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Das, Saswato (March 2010), "Hydrocarbon Superconductor Discovered", IEEE Spectrum
^ Artioli, Gianluca A.; Malavasi, Lorenzo (Dec 2013), "Superconductivity in metal-intercalated aromatic hydrocarbons", J. Mater. Chem. C, 2 (9): 1577, doi:10.1039/C3TC32326A
^ Heguri, Satoshi; Kobayashi, Mototada; Tanigaki, Katsumi (May 2015), "Questioning the existence of superconducting potassium doped phases for aromatic hydrocarbons", Phys. Rev. B, 92 (1): 014502, Bibcode:2015PhRvB..92a4502H, doi:10.1103/PhysRevB.92.014502

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Picene". Encyclopædia Britannica. Vol. 21 (11th ed.). Cambridge University Press. p. 581.

[1] Merck Index, 11th Edition, 7368.

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 206. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[3] Das, Saswato (March 2010), "Hydrocarbon Superconductor Discovered", IEEE Spectrum

[4] Artioli, Gianluca A.; Malavasi, Lorenzo (Dec 2013), "Superconductivity in metal-intercalated aromatic hydrocarbons", J. Mater. Chem. C, 2 (9): 1577, doi:10.1039/C3TC32326A

[5] Heguri, Satoshi; Kobayashi, Mototada; Tanigaki, Katsumi (May 2015), "Questioning the existence of superconducting potassium doped phases for aromatic hydrocarbons", Phys. Rev. B, 92 (1): 014502, Bibcode:2015PhRvB..92a4502H, doi:10.1103/PhysRevB.92.014502

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Picene

See also

References

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