Synthesis of BODIPY Organophotocatalysts by Boron Functionalization with Quinine Derivatives and Applications in Asymmetric Photooxygenation

Abstract

AbstractBoron dipyrromethene (BODIPY) derivatives are key dyes owing to their interesting (electro)chemical and spectroscopic properties. These features have been exploited in various scientific domains such as materials science, biomedicine or organic synthesis. In particular, heavy‐atom containing BODIPY photocatalysts have found widespread applications in photoredox and energy transfer catalysis. The covalent attachment of heavy atoms to the boron dipyrromethene core enables the population of the triplet state through intersystem crossing (ISC), which is involved in the generation of singlet oxygen via triplet‐triplet energy transfer. While the functionalization of the dipyrromethene core has been extensively studied, investigations on boron substitution is far less described. In this work, boron functionalization of diiodo‐BODIPY dyes has enabled the grafting of quinine derivatives leading to a new family of chiral photosensitizers. The photophysical properties and the photostability of these photocatalysts have been investigated in dichloromethane and methanol. Preliminary investigations in asymmetric photooxidative processes have demonstrated the synthetic potential of these BODIPY‐quinine dyes in photoorganocatalysis.