Molecular azo–imidazole photoswitches: Property tuning by substitution

Result code in 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>

Result on the web

<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

—

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

—

Czech description

—

Type

J_SC - Article in a specialist periodical, which is included in the SCOPUS database

CEP classification

—

OECD FORD branch

10400 - Chemical sciences

Project

—

Continuities

V - Vyzkumna aktivita podporovana z jinych verejnych zdroju

Publication year

2024

Confidentiality

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

Name of the periodical

Journal of Photochemistry and Photobiology A: Chemistry

ISSN

1010-6030

e-ISSN

—

Volume of the periodical

Neuveden

Issue of the periodical within the volume

Neuveden

Country of publishing house

GB - UNITED KINGDOM

Number of pages

14

Pages from-to

1-14

UT code for WoS article

001132485300001

EID of the result in the Scopus database

2-s2.0-85179482726