Highly Effective Generation of Singlet Oxygen by an Imidazole-Linked Robust Photosensitizing Covalent Organic Framework.

Abstract

Developing effective photosensitizers to initiate the generation of singlet oxygen (¹O₂) is of great significance in both chemistry and physiology. Herein, linking the photoactive porphyrin moieties by in situ-formed robust imidazole groups, a covalent organic framework (COF), <b>PyPor-COF</b>, was successfully designed and synthesized. Detailed characterizations reveal that it not only possesses high crystallinity, permanent porosity, and robust stability but also shows a semiconductive photoresponse activity. As demonstrated by electron paramagnetic resonance experiments, the COF can initiate the generation of ¹O₂ efficiently under visible-light irradiation, the efficiency of which is higher than that of the pristine porphyrin-based reactant and even higher than some commonly used commercially available photosensitizing agents. Anticancer experiments prove that it can efficiently trigger the production of ¹O₂ in a physiological environment. This work demonstrates that the imidazole-linked porphyrin-incorporated COF is a highly promising photosensitizer that can even be applied in photodynamic therapy.