Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
AuthorsFilatov, Mikhail A.
Polestshuk, Pavel M.
Flanagan, Keith J.
Boyle, Ross W.
Senge, Mathias O.
KAUST DepartmentKAUST Solar Center (KSC)
Materials Science and Engineering Program
Physical Sciences and Engineering (PSE) Division
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AbstractHeavy 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.
CitationFilatov MA, Karuthedath S, Polestshuk PM, Savoie H, Flanagan KJ, et al. (2017) Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro. Journal of the American Chemical Society 139: 6282–6285. Available: http://dx.doi.org/10.1021/jacs.7b00551.
SponsorsThis work was supported by grants from the European Commission (M.A.F., CONSORT, Grant No. 655142), Science Foundation Ireland (M.O.S. SFI IvP 13/IA/1894), and by funding from King Abdullah University of Science and Technology (KAUST). We thank Prof. Sergei Vinogradov for helpful discussions.
PublisherAmerican Chemical Society (ACS)