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Photooxidation: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Subjects: Chemistry, Organic
Contributor: Helena Kang

Photooxidation is an oxidation whose initiating or driving event is absorption of light by the substrate, a sensitizer, or a photocatalyst. The excited species can transfer energy to triplet oxygen to generate singlet oxygen, transfer an electron to produce radical ions and superoxide, or generate a semiconductor hole that removes an electron from an adsorbed substrate. A net increase in substrate oxidation state and a necessary photonic step define the concept; dark autoxidation and photochemical reactions with no oxidative change are excluded. In sensitized photooxygenation, singlet oxygen reacts with organic π systems through ene reactions, (4+2) cycloadditions, or (2+2) pathways, and it can oxidize sulfides and phosphines [1]. Other photooxidations proceed by electron transfer and radical chains rather than singlet oxygen [2]. Photooxidation is broader than photooxygenation because oxygen-atom incorporation is not required, and it differs from photoredox catalysis because catalyst turnover is not part of every photooxidation.

  • photooxidation
  • reactive oxygen species
  • photochemical oxidation
  • excited-state oxidant

Redox biology and oxidative stress • Molecular Biology • Biochemistry, Genetics and Molecular Biology • Life Sciences

References

  1. Ashwini A. Ghogare; Alexander Greer; Using Singlet Oxygen to Synthesize Natural Products and Drugs. Chem. Rev. 2016, 116, 9994-10034, 10.1021/acs.chemrev.5b00726.
  2. Ivana Pibiri; Silvestre Buscemi; Antonio Palumbo Piccionello; Andrea Pace; Photochemically Produced Singlet Oxygen: Applications and Perspectives. ChemPhotoChem 2018, 2, 535-547, 10.1002/cptc.201800076.
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