Substituent effects in N-acetylated phenylazopyrazole photoswitches
Phenylazopyrazole photoswitches proved to be valuable structural motifs for various applications ranging from materials science to medicine. Despite their potential, their structural diversity is still limited and a larger pool of substitution patterns remains to be systematically investigated. This...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.66 |
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| author | Radek Tovtik Dennis Marzin Pia Weigel Stefano Crespi Nadja A. Simeth |
| author_facet | Radek Tovtik Dennis Marzin Pia Weigel Stefano Crespi Nadja A. Simeth |
| author_sort | Radek Tovtik |
| collection | DOAJ |
| description | Phenylazopyrazole photoswitches proved to be valuable structural motifs for various applications ranging from materials science to medicine. Despite their potential, their structural diversity is still limited and a larger pool of substitution patterns remains to be systematically investigated. This is paramount as electronic effects play a crucial role in the behavior of photoswitches and a deeper understanding enables their straightforward development for specific applications. In this work, we synthesized novel N-acylpyrazole-based photoswitches and conducted a comparative study with 33 phenylazopyrazoles, comparing their photoswitching properties and the impact of electronic effects. Using UV–vis and NMR spectroscopy, we discovered that simple acylation of the pyrazole moiety leads to increased quantum yields of isomerization, long Z-isomer life-times, good spectral separation, and high photostability. |
| format | Article |
| id | doaj-art-dc6646fc7aaf4d6796155d42dc3bc590 |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-dc6646fc7aaf4d6796155d42dc3bc5902025-08-20T02:11:12ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-04-0121183083810.3762/bjoc.21.661860-5397-21-66Substituent effects in N-acetylated phenylazopyrazole photoswitchesRadek Tovtik0Dennis Marzin1Pia Weigel2Stefano Crespi3Nadja A. Simeth4Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstraße 2, 37077 Goettingen, Germany Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstraße 2, 37077 Goettingen, Germany Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstraße 2, 37077 Goettingen, Germany Department of Chemistry, Ångström laboratory, Uppsala University, Box 523, 751 20 Uppsala, Sweden Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstraße 2, 37077 Goettingen, Germany Phenylazopyrazole photoswitches proved to be valuable structural motifs for various applications ranging from materials science to medicine. Despite their potential, their structural diversity is still limited and a larger pool of substitution patterns remains to be systematically investigated. This is paramount as electronic effects play a crucial role in the behavior of photoswitches and a deeper understanding enables their straightforward development for specific applications. In this work, we synthesized novel N-acylpyrazole-based photoswitches and conducted a comparative study with 33 phenylazopyrazoles, comparing their photoswitching properties and the impact of electronic effects. Using UV–vis and NMR spectroscopy, we discovered that simple acylation of the pyrazole moiety leads to increased quantum yields of isomerization, long Z-isomer life-times, good spectral separation, and high photostability.https://doi.org/10.3762/bjoc.21.66azobenzenesazopyrazolesphotochromismphotoswitchessubstituent effects |
| spellingShingle | Radek Tovtik Dennis Marzin Pia Weigel Stefano Crespi Nadja A. Simeth Substituent effects in N-acetylated phenylazopyrazole photoswitches Beilstein Journal of Organic Chemistry azobenzenes azopyrazoles photochromism photoswitches substituent effects |
| title | Substituent effects in N-acetylated phenylazopyrazole photoswitches |
| title_full | Substituent effects in N-acetylated phenylazopyrazole photoswitches |
| title_fullStr | Substituent effects in N-acetylated phenylazopyrazole photoswitches |
| title_full_unstemmed | Substituent effects in N-acetylated phenylazopyrazole photoswitches |
| title_short | Substituent effects in N-acetylated phenylazopyrazole photoswitches |
| title_sort | substituent effects in n acetylated phenylazopyrazole photoswitches |
| topic | azobenzenes azopyrazoles photochromism photoswitches substituent effects |
| url | https://doi.org/10.3762/bjoc.21.66 |
| work_keys_str_mv | AT radektovtik substituenteffectsinnacetylatedphenylazopyrazolephotoswitches AT dennismarzin substituenteffectsinnacetylatedphenylazopyrazolephotoswitches AT piaweigel substituenteffectsinnacetylatedphenylazopyrazolephotoswitches AT stefanocrespi substituenteffectsinnacetylatedphenylazopyrazolephotoswitches AT nadjaasimeth substituenteffectsinnacetylatedphenylazopyrazolephotoswitches |