Intramolecular photosensitization for singlet oxygen trapping: Assembly of a subphthalocyanine — anthracene dyad

This study presents the synthesis and characterization of a singlet oxygen-trapping dyad based on the covalent attachment of 9-methylanthracenyl to the axial position of hexachlorosubphthalocyanine. Photophysical studies show that the dyad efficiently generates and captures singlet oxygen by the formation of the corresponding endoperoxide under light exposure and has the potential to act as an effective singlet oxygen fluorescent probe. Attempts to release singlet oxygen through thermal cycloreversion were unsuccessful, indicating a thermodynamic inhibition.