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

doi:10.1021/jacs.7b00551

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 journal › Article › peer-review

271 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 language	English (US)
Pages (from-to)	6282-6285
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	18
DOIs	https://doi.org/10.1021/jacs.7b00551
State	Published - May 2017

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10.1021/jacs.7b00551

https://repository.kaust.edu.sa/bitstream/10754/623437/1/BODIPYs%20paper%20JACS%202017-04-10.pdf

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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

@article{95aadb8b8b95412c91848407c736e30f,

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

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.",

author = "Filatov, {Mikhail A.} and Safakath Karuthedath and Polestshuk, {Pavel M.} and Huguette Savoie and Flanagan, {Keith J.} and Cindy Sy and Elisabeth Sitte and Maxime Telitchko and Fr{\'e}d{\'e}ric Laquai and Boyle, {Ross W.} and Senge, {Mathias O.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

year = "2017",

month = may,

doi = "10.1021/jacs.7b00551",

language = "English (US)",

volume = "139",

pages = "6282--6285",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "18",

}

Filatov, MA, Karuthedath, S, Polestshuk, PM, Savoie, H, Flanagan, KJ, Sy, C, Sitte, E, Telitchko, M, Laquai, F, Boyle, RW & Senge, MO 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, vol. 139, no. 18, pp. 6282-6285. https://doi.org/10.1021/jacs.7b00551

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. et al.
In: Journal of the American Chemical Society, Vol. 139, No. 18, 05.2017, p. 6282-6285.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro

AU - Filatov, Mikhail A.

AU - Karuthedath, Safakath

AU - Polestshuk, Pavel M.

AU - Savoie, Huguette

AU - Flanagan, Keith J.

AU - Sy, Cindy

AU - Sitte, Elisabeth

AU - Telitchko, Maxime

AU - Laquai, Frédéric

AU - Boyle, Ross W.

AU - Senge, Mathias O.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2017/5

Y1 - 2017/5

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/623437

UR - http://pubs.acs.org/doi/full/10.1021/jacs.7b00551

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U2 - 10.1021/jacs.7b00551

DO - 10.1021/jacs.7b00551

M3 - Article

C2 - 28407710

SN - 0002-7863

VL - 139

SP - 6282

EP - 6285

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 18

ER -

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

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CCDC 1526056: Experimental Crystal Structure Determination : 5,5-difluoro-3,7-dimethyl-10-(7b-methyl-1a,1b,2a,8b-tetrahydrotrisoxireno[3,4:4a,10:9,9a]anthra[1,2-b]oxiren-3a(7bH)-yl)-5H-4,5l-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine methanol solvate

CCDC 1526053: Experimental Crystal Structure Determination : 5,5-difluoro-1,3,7,9-tetramethyl-10-(10-methyl-9-anthryl)-5H-6,5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1526054: Experimental Crystal Structure Determination : 5,5-difluoro-1,3,7,9-tetramethyl-10-(8-methyl-1a,1b,2a,8b-tetrahydrooxireno[3,4]anthra[1,2-b]oxiren-3-yl)-5H-6,5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

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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

Abstract

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Datasets

CCDC 1526056: Experimental Crystal Structure Determination : 5,5-difluoro-3,7-dimethyl-10-(7b-methyl-1a,1b,2a,8b-tetrahydrotrisoxireno[3,4:4a,10:9,9a]anthra[1,2-b]oxiren-3a(7bH)-yl)-5H-4,5l-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine methanol solvate

CCDC 1526053: Experimental Crystal Structure Determination : 5,5-difluoro-1,3,7,9-tetramethyl-10-(10-methyl-9-anthryl)-5H-6,5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1526054: Experimental Crystal Structure Determination : 5,5-difluoro-1,3,7,9-tetramethyl-10-(8-methyl-1a,1b,2a,8b-tetrahydrooxireno[3,4]anthra[1,2-b]oxiren-3-yl)-5H-6,5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

Cite this