Singlet Oxygen: Discovery, Chemistry, C60-Sensitization†

This review article refers to the discovery of excited molecular oxygen, in particular on its lower singlet excited state ((1)Delta(g), O-1(2)). After a short report on singlet oxygen generation, the review is focused on the chemistry of this reactive species. Specifically, the three major reactions of O-1(2) with unsaturated organic substrates, namely the [4 + 2] and [2 +2] cycloadditions as well as the ene reaction, are reviewed. The proposed mechanisms of these reactions, through the years, based on experimental and computational work, have been presented. Selected examples of singlet oxygen-synthetic applications are also mentioned. The [60]fullerene and fullereno-materials photosensitized oxidations in homogeneous, as well as in heterogeneous conditions, are also comprehensively discussed. Finally, the self-sensitized photooxidation of open cage fullerenes as well as fullerenes bearing oxidizable groups is reported.

Automated summary

This review article focuses on the discovery and chemistry of excited molecular oxygen, particularly its lower singlet excited state. The reactions of singlet oxygen with unsaturated organic substrates, as well as the proposed mechanisms based on experimental and computational work, are discussed. Additionally, the synthetic applications of singlet oxygen and the photosensitized oxidations of fullerene and fullerene-materials in various conditions are comprehensively reviewed.