Molecular azo-imidazole photoswitches: Property tuning by substitution

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/75081431:_____/24:00002631

Výsledek na webu

<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>

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Photochemistry and Photobiology A-Chemistry

ISSN

1010-6030

e-ISSN

1873-2666

Svazek periodika

449

Číslo periodika v rámci svazku

April 2024

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

14

Strana od-do

115390

Kód UT WoS článku

001132485300001

EID výsledku v databázi Scopus

2-s2.0-85179482726