Electrochemical Diselenation of BODIPY Fluorophores for Bioimaging Applications and Sensitization of 1 O2
© 2023 Wiley-VCH GmbH..
We report a rapid, efficient, and scope-extensive approach for the late-stage electrochemical diselenation of BODIPYs. Photophysical analyses reveal red-shifted absorption - corroborated by TD-DFT and DLPNO-STEOM-CCSD computations - and color-tunable emission with large Stokes shifts in the selenium-containing derivatives compared to their precursors. In addition, due to the presence of the heavy Se atoms, competitive ISC generates triplet states which sensitize 1 O2 and display phosphorescence in PMMA films at RT and in a frozen glass matrix at 77 K. Importantly, the selenium-containing BODIPYs demonstrate the ability to selectively stain lipid droplets, exhibiting distinct fluorescence in both green and red channels. This work highlights the potential of electrochemistry as an efficient method for synthesizing unique emission-tunable fluorophores with broad-ranging applications in bioimaging and related fields.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:30 |
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| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 30(2024), 11 vom: 21. Feb., Seite e202303883 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Bozzi, Ícaro A O [VerfasserIn] |
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| Links: |
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| Themen: |
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene |
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| Anmerkungen: |
Date Completed 23.02.2024 Date Revised 23.02.2024 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/chem.202303883 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM365763942 |
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| 500 | |a published: Print-Electronic | ||
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| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a We report a rapid, efficient, and scope-extensive approach for the late-stage electrochemical diselenation of BODIPYs. Photophysical analyses reveal red-shifted absorption - corroborated by TD-DFT and DLPNO-STEOM-CCSD computations - and color-tunable emission with large Stokes shifts in the selenium-containing derivatives compared to their precursors. In addition, due to the presence of the heavy Se atoms, competitive ISC generates triplet states which sensitize 1 O2 and display phosphorescence in PMMA films at RT and in a frozen glass matrix at 77 K. Importantly, the selenium-containing BODIPYs demonstrate the ability to selectively stain lipid droplets, exhibiting distinct fluorescence in both green and red channels. This work highlights the potential of electrochemistry as an efficient method for synthesizing unique emission-tunable fluorophores with broad-ranging applications in bioimaging and related fields | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a BODIPY | |
| 650 | 4 | |a NIR | |
| 650 | 4 | |a electrochemistry | |
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| 650 | 4 | |a selenium | |
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| 650 | 7 | |a Boron Compounds |2 NLM | |
| 650 | 7 | |a Fluorescent Dyes |2 NLM | |
| 700 | 1 | |a Machado, Luana A |e verfasserin |4 aut | |
| 700 | 1 | |a Diogo, Emilay B T |e verfasserin |4 aut | |
| 700 | 1 | |a Delolo, Fábio G |e verfasserin |4 aut | |
| 700 | 1 | |a Barros, Luiza O F |e verfasserin |4 aut | |
| 700 | 1 | |a Graça, Gabriela A P |e verfasserin |4 aut | |
| 700 | 1 | |a Araujo, Maria H |e verfasserin |4 aut | |
| 700 | 1 | |a Martins, Felipe T |e verfasserin |4 aut | |
| 700 | 1 | |a Pedrosa, Leandro F |e verfasserin |4 aut | |
| 700 | 1 | |a da Luz, Lilian C |e verfasserin |4 aut | |
| 700 | 1 | |a Moraes, Emmanuel S |e verfasserin |4 aut | |
| 700 | 1 | |a Rodembusch, Fabiano S |e verfasserin |4 aut | |
| 700 | 1 | |a Guimarães, João S F |e verfasserin |4 aut | |
| 700 | 1 | |a Oliveira, André G |e verfasserin |4 aut | |
| 700 | 1 | |a Röttger, Sebastian H |e verfasserin |4 aut | |
| 700 | 1 | |a Werz, Daniel B |e verfasserin |4 aut | |
| 700 | 1 | |a Souza, Cauê P |e verfasserin |4 aut | |
| 700 | 1 | |a Fantuzzi, Felipe |e verfasserin |4 aut | |
| 700 | 1 | |a Han, Jianhua |e verfasserin |4 aut | |
| 700 | 1 | |a Marder, Todd B |e verfasserin |4 aut | |
| 700 | 1 | |a Braunschweig, Holger |e verfasserin |4 aut | |
| 700 | 1 | |a da Silva Júnior, Eufrânio N |e verfasserin |4 aut | |
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