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.

Picene[1]
Skeletal formula
Ball-and-stick model of the picene molecule ball
Names
Preferred IUPAC name
Picene[2]
Other names
Dibenzo[a,i]phenanthrene
3,4-Benzchrysene
β,β-Binaphthylene ethene
Identifiers
3D model (JSmol)
1912414
ChEBI
ChemSpider
ECHA InfoCard 100.005.381 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: GBROPGWFBFCKAG-UHFFFAOYSA-N checkY
  • 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
  • c5c3c2ccc1ccccc1c2ccc3c4ccccc4c5
Properties
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:
GHS08: Health hazard
Warning
H371
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).
☒N verify (what is checkY☒N ?)

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.

See alsoEdit

  • Olympicene, which has the same number of rings linked in a different way

ReferencesEdit

  1. ^ Merck Index, 11th Edition, 7368.
  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

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