Tuning the Thermal Stability of Tetra-o-chloroazobenzene Derivatives by Transforming Push-Pull to Push-Push Systems.
Azobenzene
Photoswitch
Push-pull
Push-push
Thermostability
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
03 Sep 2024
03 Sep 2024
Historique:
received:
02
05
2024
medline:
3
9
2024
pubmed:
3
9
2024
entrez:
3
9
2024
Statut:
aheadofprint
Résumé
Molecular photoswitches provide interesting tools to reversibly control various biological functions with light. Thanks to its small size and easy introduction into the biomolecules, azobenzene derivatives have been widely employed in the field of photopharmacology. All visible-light switchable azobenzenes with controllable thermostability are highly demanded. Based on the reported tetra-o-chloroazobenzenes, we synthesized push-pull systems, by introducing dialkyl amine and nitro groups as strong electron-donating and electron-withdrawing groups on the para-positions, and then transformed to push-push systems by a simple reduction step. The developed push-pull and push-push tetra-o-chloroazobenzene derivatives displayed excellent photoswitching properties, as previously reported. The half-life of the Z-isomers can be tuned from milliseconds for the push-pull system to several hours for the push-push system. The n-π* and π-π* transitions have better resolution in the push-push molecules, and excitation at different wavelengths can tune the E/Z ratio at the photostationary state. For one push-pull molecule, structure and absorption spectra obtained from theoretical calculations are compared with experimental data, along with data on the push-push counterpart.
Identifiants
pubmed: 39224068
doi: 10.1002/chem.202401737
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202401737Subventions
Organisme : Fondation de France
ID : ANR-21-CE24-0027
Informations de copyright
© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.
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