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.

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., Sitte, E., Telitchko, M., Laquai, F., Boyle, R. W., & 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: Apr 17, 2018
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• 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.
• Contract Date: May 4, 2017