Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro

Mikhail A. Filatov, Safakath Karuthedath, Pavel M. Polestshuk, Huguette Savoie, Keith J. Flanagan, Cindy Sy, Elisabeth Sitte, Maxime Telitchko, Frédéric Laquai, Ross W. Boyle, Mathias O. Senge

Research output: Contribution to journalArticlepeer-review

119 Scopus citations

Abstract

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.
Original languageEnglish (US)
Pages (from-to)6282-6285
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number18
DOIs
StatePublished - May 2017

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