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

Handle URI:
http://hdl.handle.net/10754/623437
Title:
Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
Authors:
Filatov, Mikhail A. ( 0000-0002-1640-841X ) ; Karuthedath, Safakath; Polestshuk, Pavel M.; Savoie, Huguette; Flanagan, Keith J.; Sy, Cindy; Sitte, Elisabeth; Telitchko, Maxime; Laquai, Frederic ( 0000-0002-5887-6158 ) ; Boyle, Ross W.; Senge, Mathias O. ( 0000-0002-7467-1654 )
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.
KAUST Department:
KAUST Solar Center (KSC); Materials Science and Engineering Program; Physical Sciences and Engineering (PSE) Division
Citation:
Filatov 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. Available: http://dx.doi.org/10.1021/jacs.7b00551.
Publisher:
American Chemical Society (ACS)
Journal:
Journal of the American Chemical Society
Issue Date:
14-Apr-2017
DOI:
10.1021/jacs.7b00551
Type:
Article
ISSN:
0002-7863; 1520-5126
Sponsors:
This 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.
Additional Links:
http://pubs.acs.org/doi/full/10.1021/jacs.7b00551
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Materials Science and Engineering Program; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorFilatov, Mikhail A.en
dc.contributor.authorKaruthedath, Safakathen
dc.contributor.authorPolestshuk, Pavel M.en
dc.contributor.authorSavoie, Huguetteen
dc.contributor.authorFlanagan, Keith J.en
dc.contributor.authorSy, Cindyen
dc.contributor.authorSitte, Elisabethen
dc.contributor.authorTelitchko, Maximeen
dc.contributor.authorLaquai, Fredericen
dc.contributor.authorBoyle, Ross W.en
dc.contributor.authorSenge, Mathias O.en
dc.date.accessioned2017-05-09T12:54:45Z-
dc.date.available2017-05-09T12:54:45Z-
dc.date.issued2017-04-14en
dc.identifier.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. Available: http://dx.doi.org/10.1021/jacs.7b00551.en
dc.identifier.issn0002-7863en
dc.identifier.issn1520-5126en
dc.identifier.doi10.1021/jacs.7b00551en
dc.identifier.urihttp://hdl.handle.net/10754/623437-
dc.description.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.en
dc.description.sponsorshipThis 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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/full/10.1021/jacs.7b00551en
dc.titleGeneration of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitroen
dc.typeArticleen
dc.contributor.departmentKAUST Solar Center (KSC)en
dc.contributor.departmentMaterials Science and Engineering Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalJournal of the American Chemical Societyen
dc.contributor.institutionSchool of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Science Institute, Trinity College Dublin, The University of Dublin , 152-160 Pearse Street, Dublin 2, Ireland.en
dc.contributor.institutionDepartment of Chemistry, M.V. Lomonosov Moscow State University , Leninskie Gory, 1/3 Moscow 119991, Russia.en
dc.contributor.institutionDepartment of Chemistry, University of Hull , Cottingham Road, Kingston-upon-Hull HU6 7RX, United Kingdom.en
kaust.authorKaruthedath, Safakathen
kaust.authorLaquai, Fredericen
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