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Issue 7, 2019
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Photophysical properties and application in live cell imaging of B,B-fluoro-perfluoroalkyl BODIPYs

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Abstract

The photophysical properties of newly identified B,B-fluoro-perfluoroalkyl BODIPYs (2 and 3), which possess a fluoro group and a trifluoromethyl or pentafluoroethyl group at the boron center, were investigated. B,B-Fluoro-perfluoroalkyl BODIPYs 2 and 3 exhibited better photophysical/chemical properties than B,B-difluoro-BODIPY 1, as follows: (1) higher photostability both in methanol solvent and in a live cell environment, (2) higher stability against acid degradation, and (3) improved fluorescence signal-to-noise ratios in a cell system. These favorable properties of B,B-fluoro-perfluoroalkyl BODIPYs are likely due to the highly electron-withdrawing nature of the perfluoroalkyl groups on the boron atom, which reduces the reactivity to 1O2 and strengthens the complexation of the dipyrromethene ligands to the boron atom. Thus, B,B-fluoro perfluoroalkyl BODIPYs may be useful functional molecules for various applications.

Graphical abstract: Photophysical properties and application in live cell imaging of B,B-fluoro-perfluoroalkyl BODIPYs

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Supplementary files

Article information


Submitted
09 Jan 2019
Accepted
15 Mar 2019
First published
16 Mar 2019

Med. Chem. Commun., 2019,10, 1121-1125
Article type
Research Article

Photophysical properties and application in live cell imaging of B,B-fluoro-perfluoroalkyl BODIPYs

A. Taniguchi, T. Sawazaki, Y. Shimizu, Y. Sohma and M. Kanai, Med. Chem. Commun., 2019, 10, 1121 DOI: 10.1039/C9MD00011A

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