Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat Aromaticity system. The chemical formula is . This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during incomplete combustion of organic compounds.
Occurrence and properties
Pyrene was first isolated from
coal tar, where it occurs up to 2% by weight. As a peri-fused PAH, pyrene is much more resonance-stabilized than its five-member-ring containing isomer
fluoranthene. Therefore, it is produced in a wide range of combustion conditions. For example, automobiles produce about 1 μg/km.
[Senkan, Selim and Castaldi, Marco (2003) "Combustion" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.]
Reactions
Oxidation with
Chromate ion affords perinaphthenone and then naphthalene-1,4,5,8-tetracarboxylic acid. Pyrene undergoes a series of
hydrogenation reactions and is susceptible to halogenation,
Diels-Alder additions, and nitration, all with varying degrees of selectivity.
[ Bromination occurs at one of the 3-positions.]
Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared.
Photophysics
Pyrene and its derivatives are used commercially to make and dye precursors, for example pyranine and naphthalene-1,4,5,8-tetracarboxylic acid. It has strong absorbance in UV-Vis in three sharp bands at 330 nm in DCM. The emission is close to the absorption, but moving at 375 nm.
Applications
Pyrene's fluorescence emission spectrum is very sensitive to solvent 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..]]
Pyrenes are strong electron donor materials and can be combined with several materials in order to make electron donor-acceptor systems which can be used in energy conversion and light harvesting applications.
Safety and environmental factors
Although it is not as problematic as benzopyrene, animal studies have shown pyrene is toxic to the kidneys and liver. It is now known that pyrene affects several living functions in fish and algae.
Its biodegradation has been heavily examined. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.
See also
Cited sources
Further reading
