Naphthalene Endoperoxide Heterodimer Designed for Sustained Singlet Oxygen Release

Naphthalene endoperoxides undergo thermal cycloreversion reactions to produce singlet oxygen and their parent naphthalene compounds. The rate of the reaction is dependent on the structural features, such as steric and electronic modulators. We believe that achieving a sustained release rate of singlet oxygen is important in potential biological applications. This can be achieved by tethering of two endoperoxides with different singlet oxygen release rates in a single molecular construct. Here, we report the synthesis of such a dimeric endoperoxide. Our data shows that with the biexponential reaction kinetics of singlet oxygen generation from a heterodimeric endoperoxide, it is possible to hold singlet oxygen release rates within a selected range for a longer period of time.

Automated summary

Naphthalene endoperoxides can undergo thermal cycloreversion reactions to produce singlet oxygen, and this reaction rate depends on structural features. By synthesizing a dimeric endoperoxide, it is possible to maintain singlet oxygen release rates within a selected range for a longer period of time.