Photooxygenation

A photooxygenation is a light-induced oxidation reaction in which molecular oxygen is incorporated into the product(s). Initial research interest in photooxygenation reactions arose from Oscar Raab's observations in 1900 that the combination of light, oxygen and photosensitizers is highly toxic to cells. Early studies of photooxygenation focused on oxidative damage to DNA and amino acids, but recent research has led to the application of photooxygenation in organic synthesis and photodynamic therapy.

Photooxygenation reactions are initiated by a photosensitizer, which is a molecule that enters an excited state when exposed to light of a specific wavelength (e.g. dyes and pigments). The excited sensitizer then reacts with either a substrate or ground state molecular oxygen, starting a cascade of energy transfers that ultimately result in an oxygenated molecule. Consequently, photooxygenation reactions are categorized by the type and order of these intermediates (as type I, type II, or type III reactions).

Photooxygenation reactions are easily confused with a number of processes baring similar names (i.e. photosensitized oxidation). Clear distinctions can be made based on three attributes: oxidation, the involvement of light, and the incorporation of molecular oxygen into the products:

Sensitizers (denoted "Sens") are compounds, such as fluorescein dyes, methylene blue, and polycyclic aromatic hydrocarbons, which are able to absorb electromagnetic radiation (usually in the visible range of the spectrum) and eventually transfer that energy to molecular oxygen or the substrate of photooxygenation process. Many sensitizers, both naturally occurring and synthetic, rely on extensive aromatic systems to absorb light in the visible spectrum. When sensitizers are excited by light, they reach a singlet state, ¹Sens*. This singlet is then converted into a triplet state (which is more stable), ³Sens*, via intersystem crossing. The ³Sens* is what reacts with either the substrate or ³O₂ in the three types of photooxygenation reactions.

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