Fine tuning of BODIPY’s properties via structural modifications at the 1,7-positions of BODIPY-3,5-dicarboxylates

Shambalova, Victoria E.; Larkovich, Roman V.; Aldoshin, Alexander A.; Moiseeva, Anna A.; Bunin, Dmitry A.; Safonova, Evgeniya A.; Gorbunova, Yulia G.; Nenajdenko, Valentine G.

doi:10.1016/j.jphotochem.2024.115701

Journal of Photochemistry and Photobiology A: Chemistry

2024

DOI: 10.1016/j.jphotochem.2024.115701

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Fine tuning of BODIPY’s properties via structural modifications at the 1,7-positions of BODIPY-3,5-dicarboxylates

Victoria E. Shambalova,

Roman V. Larkovich,

Alexander A. Aldoshin

et al.

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2024

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Core‐Fluorinated BODIPYs – a New Family of Highly Efficient Luminophores

Shambalova,

Aldoshin,

Bunin

et al. 2024

ChemPhotoChem

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A modular synthesis of novel series of 1,7‐difluorinated BODIPYs has been elaborated. First, the acid‐catalyzed condensation of ethyl 3‐aryl‐4‐fluoro‐1H‐pyrrole‐2‐carboxylates with aromatic aldehydes gives the corresponding dipyrromethane‐1,9‐dicarboxylates. The latter are subjected to the exhaustive reduction with lithium aluminum hydride to transform the ester moieties into methyl groups. The subsequent oxidation of the resulting 1,9‐dimethylated dipyrromethanes followed by the boron difluoride complexation afforded a family of novel core‐fluorinated BODIPYs in up to 74% yield. Photophysical properties of the resulting BODIPYs were tuned by varying of the starting fluoropyrroles and aromatic aldehydes and were studied by UV−visible and fluorescence spectroscopy. As a result, the fluorescence quantum yields of the obtained compounds reached up to 99%. In addition, their ability to generate singlet oxygen and electrochemical properties were also evaluated. As a result, a new promising family of fluorophores with a good combination of the fluorescence and photosensitizing properties was obtained. It was found that conversion of ester groups into methyl ones at the 3,5‐positions of the BODIPY core is a crucial step toward fluorescence enhancement. In addition, DFT calculations were performed to elucidate a relationship between electronic structure, geometry and photophysical properties of these BODIPYs.

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Core‐Fluorinated BODIPYs – a New Family of Highly Efficient Luminophores

Shambalova,

Aldoshin,

Bunin

et al. 2024

ChemPhotoChem

View full text Add to dashboard Cite

show abstract

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Fine tuning of BODIPY’s properties via structural modifications at the 1,7-positions of BODIPY-3,5-dicarboxylates

Cited by 1 publication

References 81 publications

Core‐Fluorinated BODIPYs – a New Family of Highly Efficient Luminophores

Core‐Fluorinated BODIPYs – a New Family of Highly Efficient Luminophores

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