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

Result code in 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>

Result on the web

<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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Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - 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/TQ03000624" target="_blank" >TQ03000624: Photoresponsive azo-polymeric materials applicable as thermal sensor</a><br>

Continuities

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

Publication year

2025

Confidentiality

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

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

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Volume of the periodical

31

Issue of the periodical within the volume

14

Country of publishing house

DE - GERMANY

Number of pages

14

Pages from-to

1-14

UT code for WoS article

001391036900001

EID of the result in the Scopus database

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