Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
2017
Filatov, Mikhail A. | Karuthedath, Safakath | Polestshuk, Pavel M. | Savoie, Huguette | Flanagan, Keith J. | Sy, Cindy | Sitte, Elisabeth | Telitchko, Maxime | Laquai, Frédéric | Boyle, Ross W. | Senge, Mathias O.
Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen (¹O2), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of ¹O₂ addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. ¹O₂ generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.
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