Abstract
An efficient synthetic protocol for the preparation of novel 1,7-difluorinated BODIPYs was elaborated. A set of novel dipyrromethanes, which are key intermediates for the target dyes, was prepared by acid-catalyzed condensation of ethyl 3-aryl-4-fluoro-1H-pyrrole-2-carboxylates with aldehydes in up to quantitative yield. Subsequent oxidation and boron difluoride complexation under microwave irradiation afforded a family of novel core-fluorinated BODIPYs in up to 92 % yield. Their photophysical properties were studied by UV–visible and fluorescence spectroscopy. In addition, DFT calculations were performed to estimate 2,6-substituents effect. This revealed that the values of the absorption and emission maxima perfectly correlated with the energy gap between the frontier orbitals.
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