Molecular azo–imidazole photoswitches: Property tuning by substitution
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F75081431%3A_____%2F24%3A00002631" target="_blank" >RIV/75081431:_____/24:00002631 - isvavai.cz</a>
Výsledek na webu
<a href="https://www-sciencedirect-com.ezproxy.techlib.cz/science/article/pii/S1010603023008559?via%3Dihub" target="_blank" >https://www-sciencedirect-com.ezproxy.techlib.cz/science/article/pii/S1010603023008559?via%3Dihub</a>
DOI - Digital Object Identifier
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Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Molecular azo–imidazole photoswitches: Property tuning by substitution
Popis výsledku v původním jazyce
Azo-imidazole photoswitches based on NH- and N-methylimidazole were designed and prepared via a convenient synthetic route. These azo-compounds were investigated by means of XRD analysis, cyclic voltammetry, thermal analysis, UV-Vis absorption spectroscopy and DFT calculations. The photoswitching was mostly affected by imidazole N-substitution with the half-life of (Z)-isomers found within the range of tens of seconds (NHimidazoles) vs. tens of hours (N-methylimidazoles). N-Methylimidazole switches can be further tuned by altering electronic effects of the appended substituents (acyl, bromine, trifluoromethyl and pentafluorosulfanyl). The latter group proved to be particularly interesting in stabilizing (Z)-isomer. Its large half-life (similar to 24 h), high photoconversion (89 %) and diminished nonlinear optical response in contrast to the (E)-isomer (beta(E/Z) - 3.82) point to a very useful strategy in introducing SF5 group in the structure of molecular switches. In summary, this detailed study demonstrates that photoswitching properties of azo-imidazoles can be significantly tuned in a broad extent by (preventing) imidazole tautomerism as well as by altering electronic effects of appended substituents.
Název v anglickém jazyce
Molecular azo–imidazole photoswitches: Property tuning by substitution
Popis výsledku anglicky
Azo-imidazole photoswitches based on NH- and N-methylimidazole were designed and prepared via a convenient synthetic route. These azo-compounds were investigated by means of XRD analysis, cyclic voltammetry, thermal analysis, UV-Vis absorption spectroscopy and DFT calculations. The photoswitching was mostly affected by imidazole N-substitution with the half-life of (Z)-isomers found within the range of tens of seconds (NHimidazoles) vs. tens of hours (N-methylimidazoles). N-Methylimidazole switches can be further tuned by altering electronic effects of the appended substituents (acyl, bromine, trifluoromethyl and pentafluorosulfanyl). The latter group proved to be particularly interesting in stabilizing (Z)-isomer. Its large half-life (similar to 24 h), high photoconversion (89 %) and diminished nonlinear optical response in contrast to the (E)-isomer (beta(E/Z) - 3.82) point to a very useful strategy in introducing SF5 group in the structure of molecular switches. In summary, this detailed study demonstrates that photoswitching properties of azo-imidazoles can be significantly tuned in a broad extent by (preventing) imidazole tautomerism as well as by altering electronic effects of appended substituents.
Klasifikace
Druh
J<sub>SC</sub> - Článek v periodiku v databázi SCOPUS
CEP obor
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OECD FORD obor
10400 - Chemical sciences
Návaznosti výsledku
Projekt
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Návaznosti
V - Vyzkumna aktivita podporovana z jinych verejnych zdroju
Ostatní
Rok uplatnění
2024
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Journal of Photochemistry and Photobiology A: Chemistry
ISSN
1010-6030
e-ISSN
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Svazek periodika
Neuveden
Číslo periodika v rámci svazku
Neuveden
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
14
Strana od-do
1-14
Kód UT WoS článku
001132485300001
EID výsledku v databázi Scopus
2-s2.0-85179482726