Molecular azo-imidazole photoswitches: Property tuning by substitution

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F24%3A39921759" target="_blank" >RIV/00216275:25310/24:39921759 - isvavai.cz</a>
Alternative codes found
RIV/75081431:_____/24:00002631
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S1010603023008559" target="_blank" >http://www.sciencedirect.com/science/article/pii/S1010603023008559</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jphotochem.2023.115390" target="_blank" >10.1016/j.jphotochem.2023.115390</a>

Result language
angličtina
Original language name
Molecular azo-imidazole photoswitches: Property tuning by substitution
Original language description
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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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