Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties - Université de Bourgogne Accéder directement au contenu
Article Dans Une Revue Tetrahedron Letters Année : 2019

Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties

Résumé

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).

Domaines

Chimie organique
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Dates et versions

hal-02320124 , version 1 (21-12-2021)

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Paternité - Pas d'utilisation commerciale

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Valentin Quesneau, Benoît Roubinet, Pierre-Yves Renard, Anthony Romieu. Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties. Tetrahedron Letters, 2019, 60 (48), pp.151279. ⟨10.1016/j.tetlet.2019.151279⟩. ⟨hal-02320124⟩
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