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

卷:60

Article

Quesneau, Valentin¹  Roubinet, Benoit²  Renard, Pierre-Yves²  Romieu, Anthony¹ 

[1] Univ Bourgogne Franche Comte, CNRS, UMR 6302, ICMUB, 9 Ave Alain Savary, F-21078 Dijon, France

[2] Normandie Univ, UNIROUEN, INSA Rouen, IRCOF,CNRS,COBRA,UMR 6014, 1 Rue Tesnieres, F-76821 Mont St Aignan, France

关键词: Aggregation-induced emission (AIE);    Coumarin;    Covalent-assembly;    Fluorescent probe;   

DOI  :  10.1016/j.tetlet.2019.151279

来源: Elsevier

【 摘 要 】

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 (WE). (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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