Release of Singlet Oxygen from Organic Peroxides under Mild Conditions. Issue 7 (16th April 2018)

• Record Type: Journal Article
• Authors: Fudickar, Werner; Linker, Torsten
• Is Part Of: ChemPhotoChem. Volume 2:Issue 7(2018)
• Page Start: 548
• Page End: 558
• Publication Date: 2018-04-16
• Subjects: donor-acceptor systems -- oxygenation -- peroxides -- polycycles -- retro reactions; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.201700235
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: Singlet oxygen can be released in the dark in nearly quantitative yield from endoperoxides of naphthalenes, anthracenes and pyridones as an alternative to its generation by photosensitization. Recently, new donor systems have been designed which operate at very low temperatures but which are prepared from their parent forms at acceptable rates. Enhancement of the reactivity of donors is conveniently achieved by the design of the substitution pattern or through the use of plasmonic heating of nanoparticle‐bound donors. The most important aim of these donor molecules is to transfer singlet oxygen in a controlled and directed manner to a target. Low temperatures and the linking between donors and acceptors reduce the random walk of oxygen and may force an attack at the desired position. By using chiral donor systems, new stereocenters might be introduced into prochiral acceptors. Abstract : Cool peroxides ! An appropriate substitution pattern or the use of plasmonic heating leads to a series of singlet oxygen donors, which transfer oxygen at very low temperatures to a specific target. In this vein, this Minireview summarizes recent results on organic endoperoxides, detailing reaction mechanisms, alternative approaches for inducing 1 O2 release and discussing how the efficiency can be enhanced through intramolecular 1 O2 transfer.