Property Tuning in N-Methylpyrrole Azo-Photoswitches via Modification of the Peripheral Substituents

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F75081431%3A_____%2F25%3A00002695" target="_blank" >RIV/75081431:_____/25:00002695 - isvavai.cz</a>

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404221" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404221</a>

DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Property Tuning in N-Methylpyrrole Azo-Photoswitches via Modification of the Peripheral Substituents

Popis výsledku v původním jazyce

Differently substituted pyrrole-azo–benzene molecular photoswitches were prepared in a straightforward synthetic way. Their fundamental properties were investigated by XRD analysis, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, UV–Vis absorption spectroscopy, Hyper-Rayleigh Scattering, and NMR spectroscopy; the experimental results were further corroborated by DFT calculations. Thermal robustness, the HOMO/LUMO levels, and the absorption properties were altered mostly by substituting the N–methylpyrrole moiety and further fine-tuned by modifying the benzene substituents. The pyrrole substituent also proved crucial for the second-order non–linear optical (NLO) response as well as the photoswitching performance. Both fast and slow molecular switches can be designed with the half–life of the (Z) –isomer ranging from 48 seconds to 23.28 hours and the E/Z molar ratio up to 12/88. This comprehensive study allowed elucidation of the fundamental structure-property relationships and subsequently addresses the key aspects of the property tuning via substitution in molecular azo-photoswitches.

Název v anglickém jazyce

Property Tuning in N-Methylpyrrole Azo-Photoswitches via Modification of the Peripheral Substituents

Popis výsledku anglicky

Differently substituted pyrrole-azo–benzene molecular photoswitches were prepared in a straightforward synthetic way. Their fundamental properties were investigated by XRD analysis, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, UV–Vis absorption spectroscopy, Hyper-Rayleigh Scattering, and NMR spectroscopy; the experimental results were further corroborated by DFT calculations. Thermal robustness, the HOMO/LUMO levels, and the absorption properties were altered mostly by substituting the N–methylpyrrole moiety and further fine-tuned by modifying the benzene substituents. The pyrrole substituent also proved crucial for the second-order non–linear optical (NLO) response as well as the photoswitching performance. Both fast and slow molecular switches can be designed with the half–life of the (Z) –isomer ranging from 48 seconds to 23.28 hours and the E/Z molar ratio up to 12/88. This comprehensive study allowed elucidation of the fundamental structure-property relationships and subsequently addresses the key aspects of the property tuning via substitution in molecular azo-photoswitches.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/TQ03000624" target="_blank" >TQ03000624: Fotoresponzivní azo-polymerní materiály aplikovatelné jako tepelný senzor</a><br>

Návaznosti

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

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

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Svazek periodika

31

Číslo periodika v rámci svazku

14

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

1-14

Kód UT WoS článku

001391036900001

EID výsledku v databázi Scopus

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