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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA21-01057S" target="_blank" >GA21-01057S: Nové organické polovodiče pro budoucí bioelektronické zařízení pro regenerativní medicínu</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2022

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

—

Svazek periodika

430

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

8

Strana od-do

1-8

Kód UT WoS článku

000804941200005

EID výsledku v databázi Scopus

2-s2.0-85129691596