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Updated: Jul 4, 2025

Conventional BODIPY Conjugates for Live-Cell Super-Resolution Microscopy and Single-Molecule Tracking
Published on: June 8, 2020
Solvent and alkyl substitution effects on charge-transfer mediated triplet state generation in BODIPY dyads: a
Yasi Dai1,2, Angela Dellai1, Elena Bassan1,2
1Department of Chemistry Giacomo Ciamician, University of Bologna, Bologna, Italy.
Abstract:
Donor-acceptor dyads based on BODIPYs have been recently employed to enhance the formation of triplet excited states with the process of spin-orbit charge transfer intersystem crossing (SOCT-ISC) which does not require introduction of transition metals or other heavy atoms into the molecule. In this work we compare two donor-acceptor dyads based on meso-naphthalenyl BODIPY by combining experimental and computational investigations. The photophysical and electrochemical characterization reveals a significant effect of alkylation of the BODIPY core, disfavoring the SOCT-ISC mechanism for the ethylated BODIPY dyad. This is complemented with a computational investigation carried out to rationalize the influence of ethyl substituents and solvent effects on the electronic structure and efficiency of triplet state population via charge recombination (CR) from the photoinduced electron transfer (PeT) generated charge-transfer (CT) state. Time dependent-density functional theory (TD-DFT) calculations including solvent effects and spin-orbit coupling (SOC) calculations uncover the combined role played by solvent and alkyl substitution on the lateral positions of BODIPY.
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