Fast E/Z UV-light response T-type photoswitching of phenylene-thienyl imines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F22%3APU144770" target="_blank" >RIV/00216305:26310/22:PU144770 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1016/j.jphotochem.2022.113994" target="_blank" >https://doi.org/10.1016/j.jphotochem.2022.113994</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jphotochem.2022.113994" target="_blank" >10.1016/j.jphotochem.2022.113994</a>

Result language
angličtina
Original language name
Fast E/Z UV-light response T-type photoswitching of phenylene-thienyl imines
Original language description
New types of imine switches containing an alkylated para-bis(2-thienyl)phenylene moiety have been synthesized and studied. A bis substituted 2,4-diiminotoluene with phenylene-thienyl unit has also been synthesized and studied to evaluate the bifunctional switching of the imine bonds. Fast E/Z response in toluene and acetonitrile under 365 nm UV-light illumination was observed. It was found that the thermally unstable Z isomers are recovered to E ones in the dark by different rate constants depending on the solvent polarity, which refers to the T-type photochromic switches. The DFT calculations have shown that the switched Z forms are characterized by near perpendicular (T-shaped) orientation of the aromatic amine rings with respect to the thiophene one. The emission exhibited a significant bathochromism varying the solvent polarity, with Stokes shifts reaching values in the order 10 000 cm-1, while the absorption remained almost unaffected. Therefore, the relationship between E/Z switching response and solvent sensitivity of the emissions was estimated. The behaviour of the compounds suggests a rapid T-type E/Z/E isomerization cycle and dynamic control over the light-driven geometrical changes of the imine bond.
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
<a href="/en/project/GA21-01057S" target="_blank" >GA21-01057S: Novel organic semiconductors for future bioelectronics devices for regenerative medicine</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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