Abstract
The synthesis and resolution of a class of chiral organic fluorophores, axially chiral 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (Ax*-BODIPY), is described. Ax*-BODIPYs were prepared through a modular synthesis combined with a late stage Heck functionalisation. Resolution was achieved by preparative chiral HPLC. Absolute stereochemical assignment was performed by comparison of experimental ECD spectra with TD-DFT calculations.
Highlights
Ax*-boron-dipyrromethene dyes (BODIPY) were prepared through a modular synthesis combined with a late stage Heck functionalisation
Resolution was achieved by preparative chiral HPLC
Absolute stereochemical assignment was performed by comparison of experimental electronic circular dichroism (ECD) spectra with TD-DFT calculations
Summary
The synthesis and resolution of a class of chiral organic fluorophores, axially chiral 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (Ax*-BODIPY), is described. Absolute stereochemical assignment was performed by comparison of experimental ECD spectra with TD-DFT calculations. In this manuscript we present a general approach for the synthesis, resolution and absolute stereochemical determination of a class of axially chiral BODIPYs (Ax*-BODIPY), based on restricted rotation of aromatic substituents in the meso-position (or 8-position).
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