Effect of Twisting on the Capture and Release of Singlet Oxygen by Tethered Twisted Acenes.

ABSTRACT: The use of polyaromatic hydrocarbons to capture and release singlet oxygen is of considerable importance in materials chemistry, synthesis, and photodynamic therapy. Here we studied the ability of a series of tethered twistacenes, possessing different degrees of backbone twist, to capture and release singlet oxygen via the reversible Diels-Alder reaction. When the twistacene acts as both a sensitizer and a diene, the photo-oxidation rate depends on the extinction coefficient of the irradiation wavelength. However, when the twistacenes function solely as a diene, the rate of photo-oxidation increases with increasing twist. The rate of the reverse reaction, the singlet oxygen release, also increases with increasing twist. The calculated transition state energy decreases with increasing twist

SUBMITTER: Bedi A 

PROVIDER: S-EPMC8323967 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature