Pyrene

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C₁₆H₁₀. This yellow crystalline 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.

Properties

Pyrene is a flat molecule that can intercalate into DNA, while it is not a particularly potent mutagen, it is quite toxic and teratogenic. Pyrene is also used as a probe to determine the polarity of a solvent. It also has a high quantum yield of fluorescence, and because of this it is used in biochemistry experiments as a fluorescent probe, particularly when studying lipids.

Occurrence

Pyrene and its derivatives are products of combustion and are produced by fossil fuel burning for heat and power, making them common air pollutants. Pyrene is not a major constituent of tar, but it is a component of soot, which is a byproduct of the combustion of diesel and other fuels.

Uses

Pyrene is used commercially to make dyes and dye precursors, and it is also used in research as a reference standard for the spectroscopic quantification of polycyclic aromatic hydrocarbons.

Health effects

Exposure to pyrene can cause skin irritation and inflammation. Long-term or repeated exposures can lead to more serious health effects, including cancer.

See also

• Polycyclic aromatic hydrocarbon
• Benzene
• Tar
• Soot

Pyrene

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  Pyrene structure
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  Br4Py self-assembly on gold
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  Br4Py self-assembly on gold (second image)
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  Pyrene numbering