Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch
Abstract: Reversibly switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. This work presents a symmetrical benzothiadiazole (BTD) derivative with a high fluorescence quantum yield in solution and in the crystalline state and shows by spectroelectrochemical analysis that reversible switching of UV absorption in the neutral state, to broadband Vis/NIR absorption in the 1st oxidized state, to sharp band Vis absorption in the 2nd oxidized state, is possible. For the one‐electron oxidized species, formation of a delocalized radical is confirmed by electron paramagnetic resonance spectroelectrochemistry. Furthermore, our results reveal an increasing quinoidal distortion upon the 1st and 2nd oxidation, which can be used as the leitmotif for the development of BTD based redox switches.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch ; volume:26 ; number:72 ; year:2020 ; pages:17361-17365 ; extent:5
Chemistry - a European journal ; 26, Heft 72 (2020), 17361-17365 (gesamt 5)
- Creator
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Rietsch, Philipp
Sobottka, Sebastian
Hoffmann, Katrin
Popov, Alexey A.
Hildebrandt, Pascal
Sarkar, Biprajit
Resch-Genger, Ute
Eigler, Siegfried
- DOI
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10.1002/chem.202004009
- URN
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urn:nbn:de:101:1-2022060417261459121087
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:23 AM CEST
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Associated
- Rietsch, Philipp
- Sobottka, Sebastian
- Hoffmann, Katrin
- Popov, Alexey A.
- Hildebrandt, Pascal
- Sarkar, Biprajit
- Resch-Genger, Ute
- Eigler, Siegfried
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Determination of the Photoluminescence Quantum Yield of Dilute Dye Solutions (IUPAC Technical Report)
Design, Synthese und Charakterisierung von Fluoreszenzstandards und Fluoreszenzmarkern für die zeitaufgelöste Fluorometrie
The 2023 Nobel Prize in Chemistry: Quantum dots
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Fluorescence calibration standards made from broadband emitters encapsulated in polymer beads for fluorescence microscopy and flow cytometry
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Quantification of anisotropy-related uncertainties in relative photoluminescence quantum yield measurements of nanomaterials - semiconductor quantum dots and rods
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