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Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Dual‐State Emissive π‐Extended Salicylaldehyde Fluorophores: Synthesis, Photophysical Properties and First‐Principle Calculations

Résumé

The search for simple, low-cost, versatile, easily accessible, stimuli-responsive, highly emissive molecular fluorophores emitting both in solution and in the solid-state has prompted us to investigate the optical properties of a series of synthetically accessible salicyladehyde derivatives possessing a π-conjugated moiety at their 4-position. These dyes are mainly known as synthetic intermediates but can also display sizeable Excited-State Intramolecular Proton Transfer (ESIPT) fluorescence owing to the presence of a 6-membered H-bonded ring in their structure. The photophysical properties of these compounds have been studied in solution (multiple solvents) and in the solid-state, as doped in PMMA films, leading to the observation of a pronounced fluorosolvatochromism. Modification of the spacer (ethynyl, vinyl or direct connection) involved the π-delocalization triggers major differences in terms of maximum emission wavelength and fluorescence quantum yields in the various media studied. All photophysical observations are rationalized by first-principle calculations.

Domaines

Chimie organique
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Dates et versions

hal-03357855 , version 1 (29-09-2021)

Identifiants

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Timothée Stoerkler, Denis Frath, Denis Jacquemin, Julien Massue, Gilles Ulrich. Dual‐State Emissive π‐Extended Salicylaldehyde Fluorophores: Synthesis, Photophysical Properties and First‐Principle Calculations. European Journal of Organic Chemistry, 2021, 2021 (26), pp.3726-3736. ⟨10.1002/ejoc.202100650⟩. ⟨hal-03357855⟩
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