Picene

For other uses, see Picene (disambiguation) and Piceno (disambiguation).

Picene

Names
IUPAC name Dibenzo[a,i]phenanthrene
Other names Picene 3,4-Benzchrysene β,β-Binaphthylene ethene
Identifiers
CAS Number	213-46-7 N
ChEBI	CHEBI:33090 Y
ChemSpider	8808 Y
Jmol 3D model	Interactive image
KEGG	C19500 N
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
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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. However, due to the apparent inability to reproduce this work, the superconducting nature of doped picene has been met with heavy scepticism.

References

 This article incorporates text from a publication now in the public domain: