Pyrene

Pyrene

Chembox new
Name = Pyrene
ImageFile = Pyrene.svg
ImageSize = 160px
ImageName = Pyrene
IUPACName = pyrene
OtherNames = benzo(d,e,f)phenanthrene
Section1 = Chembox Identifiers
SMILES = C12=CC=C3C=CC=C4
C=CC(C2=C34)=CC=C1
CASNo = 129-00-0
RTECS = UR2450000
Section2 = Chembox Properties
Formula = carbon16hydrogen10
MolarMass = 202.25 g/mol
Appearance = colorless solid(yellow impurities are often found at trace levels in many samples).
Density = 1.271 g/ml
Solubility = 0.135 mg/l
MeltingPt = 145-148 °C (418-421 K)
BoilingPt = 404 °C (677 K)
Section3 = Chembox Structure
CrystalStruct =
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = irritant
NFPA-H = 1
NFPA-F =
NFPA-R =
FlashPt = non-flammable
RPhrases = 36/37/38-45-53
SPhrases = 24/25-26-36
Section8 = Chembox Related
Function = PAHs
OtherFunctn = benzopyrene

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a large, flat aromatic system. It is the smallest peri-fused polycyclic aromatic hydrocarbon - one where the rings are fused through more than one face. It forms during incomplete combustion of organic material and therefore can be isolated from coal tar along with a broad range of related compounds. As a peri-fused PAH, pyrene is much more resonance stabilized than its five-member-ring containing isomer fluoranthene. Thus, it is produced in a wider range of combustion conditions. Pyrene is a colorless solid. Animal studies have shown pyrene is toxic to the kidneys and the liver.

Pyrene and its derivatives is used commercially to make dyes (for example pyranine), pesticides, pharmaceuticals, and plastics. It is also a valuable molecular probe for fluorescence spectroscopy, having a high quantum yield and lifetime (0.65 and 410 nanosecond, respectively, in ethanol at 293K). Its fluorescence emission spectrum is very sensitive to the solvent's polarity, so pyrene has been used as a probe to determine solvent environments. This is due to its excited state having a different, non-planar structure than the ground state. Certain emission bands are unaffected, but others vary in intensity due to the strength of interaction with a solvent.

Pyrene adopts a dimeric structure, with molecules arranged in sandwiched pairs in order to form lattice units. This results in a high degree of symmetry, belonging to the C2h symmetry group. In solution, dimers exhibit high wavelength fluorescence and also excimer formation.

References

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External links

* [http://www.chemicalland21.com/arokorhi/industrialchem/organic/PYRENE.htm Pyrene]


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  • pyrène — [ pirɛn ] n. m. • 1858; du rad. chim. pyr , gr. pur « feu » ♦ Chim. Hydrocarbure polycyclique de formule C16H10, que l on extrait du goudron de houille. ● pyrène nom masculin Hydrocarbure polycyclique aromatique C16H10, qui se rencontre dans les… …   Encyclopédie Universelle

  • Pyrene — Py rene, n. [Gr. ? fire.] (Chem.) One of the less volatile hydrocarbons of coal tar, obtained as a white crystalline substance, {C16H10}. [1913 Webster] …   The Collaborative International Dictionary of English

  • Pyrene — Py rene, n. (Bot.) Same as {Pyrena}. [1913 Webster] …   The Collaborative International Dictionary of English

  • Pyréne — PYRÉNE, es, Gr. Πυρήνη, ης, des Bebrix Tochter, mit welcher Herkules seine Händel hatte. Sie soll auf dem pyrenäischen Gebirge begraben seyn, und solches von ihr den Namen haben. Nat. Com. l. VII. c. 1. p. 692 …   Gründliches mythologisches Lexikon

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