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Reinvestigation of the Synthesis of "Covalent-Assembly" Type Probes for Fluoride Ion Detection. Identification of Novel 7-(Diethylamino)coumarins with Aggregation-Induced Emission Properties

preprint
submitted on 28.08.2019 and posted on 30.08.2019 by Valentin QUESNEAU, Benoît ROUBINET, Pierre-Yves RENARD, Anthony ROMIEU
An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of "covalent-assembly"-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).

Funding

ANR-18-CE39-0014

History

Email Address of Submitting Author

anthony.romieu@u-bourgogne.fr

Institution

UBFC

Country

France

ORCID For Submitting Author

0000-0002-2300-4499

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1 28-08-2019

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