Heteroaryl-Substituted Bis-Anils: Aggregation-Induced Emission (AIE) Derivatives with Tunable ESIPT Emission Color and pH Sensitivity.
ESIPT
Schiff base
aggregation-induced emission
fluorescence
pH
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
07 Mar 2023
07 Mar 2023
Historique:
received:
02
12
2022
pubmed:
17
12
2022
medline:
17
12
2022
entrez:
16
12
2022
Statut:
ppublish
Résumé
The two-step synthesis, structural, and photophysical properties of a series of heteroaryl-substituted bis-anil derivatives presenting aggregation-induced emission (AIE) coupled with an excited-state intramolecular proton transfer (ESIPT) process is described. The fluorescence color of the aggregates can be fine tuned by changing the electronic nature of the peripheral substitution, leading to a wide range of emission wavelengths (from green to the near infra-red). Moreover, upon introduction of strong electron-withdrawing groups such as cyano (CN), a competition between ESIPT and deprotonation is observed leading to the emission of the anionic species at low water percentage. This observation led to the synthesis of an additional mixed AIE fluorophore, functionalized by methoxy groups on one side and cyano groups on the other side. Upon addition of water, this dye displays first anionic emission, followed by typical AIE/ESIPT red fluorescence upon formation of the aggregates. TD-DFT calculations on selected AIE dyes were performed to rationalize the nature of the emissive transitions in these derivatives.
Identifiants
pubmed: 36524677
doi: 10.1002/chem.202203766
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203766Informations de copyright
© 2022 Wiley-VCH GmbH.
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A 13C NMR spectrum was not obtained due to inherent low solubility in CDCl3 or DMSO.