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Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch
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 solut...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839704/ https://www.ncbi.nlm.nih.gov/pubmed/32997430 http://dx.doi.org/10.1002/chem.202004009 |
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author | Rietsch, Philipp Sobottka, Sebastian Hoffmann, Katrin Popov, Alexey A. Hildebrandt, Pascal Sarkar, Biprajit Resch‐Genger, Ute Eigler, Siegfried |
author_facet | Rietsch, Philipp Sobottka, Sebastian Hoffmann, Katrin Popov, Alexey A. Hildebrandt, Pascal Sarkar, Biprajit Resch‐Genger, Ute Eigler, Siegfried |
author_sort | Rietsch, Philipp |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7839704 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-78397042021-02-02 Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch Rietsch, Philipp Sobottka, Sebastian Hoffmann, Katrin Popov, Alexey A. Hildebrandt, Pascal Sarkar, Biprajit Resch‐Genger, Ute Eigler, Siegfried Chemistry Communications 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. John Wiley and Sons Inc. 2020-11-23 2020-12-23 /pmc/articles/PMC7839704/ /pubmed/32997430 http://dx.doi.org/10.1002/chem.202004009 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Rietsch, Philipp Sobottka, Sebastian Hoffmann, Katrin Popov, Alexey A. Hildebrandt, Pascal Sarkar, Biprajit Resch‐Genger, Ute Eigler, Siegfried Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title | Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title_full | Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title_fullStr | Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title_full_unstemmed | Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title_short | Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch |
title_sort | between aromatic and quinoid structure: a symmetrical uv to vis/nir benzothiadiazole redox switch |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839704/ https://www.ncbi.nlm.nih.gov/pubmed/32997430 http://dx.doi.org/10.1002/chem.202004009 |
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