期刊
DYES AND PIGMENTS
卷 221, 期 -, 页码 -出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2023.111822
关键词
BODIPY; Dipyrromethane; Pyrrole; Fluorine; Fluorinated building blocks
An efficient synthetic protocol for the preparation of novel 1,7-difluorinated BODIPYs was elaborated. Their photophysical properties were studied and the effect of 2,6-substituents was evaluated using DFT calculations.
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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