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.
Reactions
Oxidation with chromate affords perinaphthenone and then naphthalene-1,4,5,8-tetracarboxylic acid. It undergoes a series of hydrogenation reactions, and it is susceptible to halogenation, Diels-Alder additions, and nitration, all with varying degrees of selectivity. Bromination occurs at one of the 3-positions.
Photophysics
Pyrene and its derivatives are used commercially to make dyes 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. The morphology of the signals change with the solvent. Its derivatives are also valuable molecular probes via fluorescence spectroscopy, having a high quantum yield and lifetime. Pyrene was the first molecule for which excimer behavior was discovered. Such excimer appears around 450 nm. Theodor Förster reported this in 1954.
Applications
Pyrene's fluorescenceemission 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.. 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. Experiments in pigs show that urinary 1-hydroxypyrene is a metabolite of pyrene, when given orally. 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.
