Phenanthrenequinone Photoclick Chemistry

Photoclick reactions, as a novel and distinctive type of click reaction that combines the principle of photochemistry and click chemistry, offer an optimal platform for achieving selective product formation, high conversion rates, rapid reaction kinetics, compatibility with diverse functional groups and mild reaction conditions. These reactions enable precise synthesis, demonstrate exceptional spatiotemporal resolution, and have a wide range of applications, which includes but is not limited to drug discovery, polymer synthesis, materials science, and bioimaging. The 9,10-phenanthrenequinone (PQ) - electron rich alkene (ERA) photocycloadditions photoclick reaction deserves special attention due to its good kinetics, biocompatibility, and ability to respond to visible light, making it highly captivating. However, further comprehensive research is essential to advance our understanding of this reaction, develop novel alternatives and unravel its underlying mechanisms, paving the way for future advancements in this field.
The main focus of this dissertation is the visible and near-infrared light (NIR) light-induced PQ-ERA photoclick reaction system. It encompasses several key aspects, including investigating the reaction mechanism, optimizing reactivity through the development of new traps, achieving a redshift of the driving wavelength using strategies like triplet-triplet energy transfer (TTET) and upconverting nanoparticles (UCNP), and exploring practical applications such as synthesizing 18F-PET tracers.