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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
Open accessAbstract
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.
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Cites
BODIPY dyes in photodynamic therapy
Kamkaew, A., Lim, S. H., Lee, H. B., Kiew, L. V., Chung, L. Y., & Burgess, K. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35216h · Cited by 2,104
Cited by
Photosensitizers with Aggregation‐Induced Emission: Materials and Biomedical Applications
Hu, F., Xu, S., & Liu, B. (2018) · Advanced Materials · doi:10.1002/adma.201801350 · Cited by 859
Wang, C., Chi, W., Qiao, Q., Tan, D., Xu, Z., & Liu, X. (2021) · Chemical Society Reviews · doi:10.1039/d1cs00239b · Cited by 710
Nguyen, V.-N., Yan, Y., Zhao, J., & Yoon, J. (2021) · Accounts of Chemical Research · doi:10.1021/acs.accounts.0c00606 · Cited by 650
Nguyen, V., Yim, Y., Kim, S., Ryu, B., Swamy, K. M. K., Kim, G., Kwon, N., Kim, C., Park, S., & Yoon, J. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202002843 · Cited by 326
Hou, Y., Zhang, X., Chen, K., Liu, D., Wang, Z., Liu, Q., Zhao, J., & Barbon, A. (2019) · Journal of Materials Chemistry C · doi:10.1039/c9tc04285g · Cited by 266
Metadata
- Authors
- 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.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-05-01
- Volume
- 139
- Issue
- 18
- Pages
- 6282-6285
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2606257843
- Cited by
- 345
- References
- 1
- FWCI
- 14.34
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- The paper
- 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. https://doi.org/10.1021/jacs.7b00551
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