Picene

Picene[1]
IUPAC name Dibenzo[a,i]phenanthrene
Other names Picene 3,4-Benzchrysene β,β-Binaphthylene ethene
Identifiers
CAS number	213-46-7 N
ChemSpider	8808 Y
KEGG	C19500 N
ChEBI	CHEBI:33090 Y
Jmol-3D images	Image 1
SMILES c5c3c2ccc1ccccc1c2ccc3c4ccccc4c5
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 Y Key: GBROPGWFBFCKAG-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C22H14
Molar mass	278.33 g/mol
Density	? g/cm3
Melting point	366-367 °C
Boiling point	518-520 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 shown to exhibit superconductive properties.^[2]

References

1. ↑ Merck Index, 11th Edition, 7368.
2. ↑ Das, Saswato (March 2010), "Hydrocarbon Superconductor Discovered", IEEE Spectrum  Cite uses deprecated parameters (help)

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