Heteroaryl‐Substituted Bis‐Anils: Aggregation‐Induced Emission (AIE) Derivatives with Tunable ESIPT Emission Color and pH Sensitivity - CNRS - Centre national de la recherche scientifique Access content directly
Journal Articles Chemistry - A European Journal Year : 2023

Heteroaryl‐Substituted Bis‐Anils: Aggregation‐Induced Emission (AIE) Derivatives with Tunable ESIPT Emission Color and pH Sensitivity

Timothée Stoerkler
  • Function : Author
Gilles Ulrich
Denis Jacquemin
  • Function : Correspondent author
  • PersonId : 895275

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Abstract

Abstract 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.
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Dates and versions

hal-04283031 , version 1 (13-11-2023)

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Timothée Stoerkler, Pascal Retailleau, Gilles Ulrich, Denis Jacquemin, Julien Massue. Heteroaryl‐Substituted Bis‐Anils: Aggregation‐Induced Emission (AIE) Derivatives with Tunable ESIPT Emission Color and pH Sensitivity. Chemistry - A European Journal, 2023, 29 (14), ⟨10.1002/chem.202203766⟩. ⟨hal-04283031⟩
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