New Insights into the Exploitation of BODIPY Derivatives as Organic Photocatalyst

Ana Da Lama, Beatrice Bartolomei, Cristian Rosso, Giacomo Filippini,
M. Montserrat Martínez, Luis A. Sarandeses, and Maurizio Prato

Abstract

Eur. J. Org. Chem. 2022, e202200622, doi: 10.1002/ejoc.202200622

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Boron-dipyrromethene complexes (BODIPYs) are attracting a growing interest for their notable photophysical properties.
Specifically, their application in organic photocatalysis is receiving particular attention thanks to their ability to undergo
both electron and energy transfer processes, thus acting as promising photoredox catalysts and photosensitizers. Although
the number of examples employing these organic dyes is constantly increasing, there are not so many studies that
correlate their chemical composition to their photocatalytic activity. In this work, a rationally designed structure-activity
relationship study was performed by selecting a synthetically relevant atom transfer radical addition (ATRA) reaction as a
benchmark. We demonstrated how the presence of heavy atoms in the chromophore’s core turned out to be essential for
achieving high reactivity levels. On the contrary, electronwithdrawing groups in position 8 (meso) undermined the
catalytic performances, in agreement with the proposed reaction mechanism.