AtropFluoPhoto · Stereoselective Synthesis of Atropisomeric Fluorophores for Asymmetric Photocatalysis

Arylated heterocyclic systems, such as fluorophores, have a long history as a component in functional materials. They are extremely useful platforms for a broad application in material science, biological imaging or organic synthesis, owing to their unique chemical, photophysical, and electrochemical properties. The development of an efficient route to prepare this type of heterocycles continues to attract interest for various applications, while only limited to the synthesis of symmetric fluorophores in racemic fashion. Introducing a chiral element into the molecules is of great significance for drug discovery, the design of catalysts for asymmetric synthetic photochemistry and other enantioselective methods. The resulting fluorophore bearing enantiospecific sensing platforms may also find potential applications in the enantioselective recognition of chiral small molecules or bioactive compounds such as DNA. Hence, the aim of the proposed AtropFluoPhoto is to develop a strategy for the asymmetric catalytic synthesis of chiral heterocyclic fluorophores. We plan to investigate different activation modes, such as chiral Brønsted acid and anion-binding catalysis, to achieve the construction of axially chiral fluorophores in intramolecular or intermolecular reactions. With the knowledge of their unique chemical and photophysical properties, we will then particularly explore their practical application in synthesis and novel catalyst design for asymmetric catalysis in photocatalysis. The proposed research will greatly broaden the fellow´s competencies and help him reach the professional maturity for a future academic career.