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), PyPor-COF, 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.