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Generation of triplet excited states via photoinduced electron transfer in meso-anthra-BODIPY: fluorogenic response toward singlet oxygen in solution and in vitro

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.

Authors

Mikhail A. Filatov

Safakath Karuthedath

Pavel M. Polestshuk

Huguette Savoie

Keith J. Flanagan

Cindy Sy

Elisabeth Sitte

Maxime Telitchko

Frédéric Laquai

Mathias O. Senge



Abstract

© 2017 American Chemical Society. 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 ( 1 O2), 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 1 O 2 addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. 1 O 2 generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.

Citation

Filatov, M. A., Karuthedath, S., Polestshuk, P. M., Savoie, H., Flanagan, K. J., Sy, C., …Senge, M. O. (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(18), 6282-6285. https://doi.org/10.1021/jacs.7b00551

Journal Article Type Article
Acceptance Date Apr 13, 2017
Online Publication Date Apr 13, 2017
Publication Date May 10, 2017
Deposit Date May 4, 2017
Publicly Available Date Mar 28, 2024
Journal Journal of the American Chemical Society
Print ISSN 0002-7863
Electronic ISSN 1520-5126
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 139
Issue 18
Pages 6282-6285
DOI https://doi.org/10.1021/jacs.7b00551
Keywords Colloid and Surface Chemistry; Biochemistry; General Chemistry; Catalysis
Public URL https://hull-repository.worktribe.com/output/451013
Publisher URL http://pubs.acs.org/doi/full/10.1021/jacs.7b00551
Additional Information Copy of article first published in: Journal of the American Chemical Society, 2017, v.139, issue 18.

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Copyright Statement
This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.





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