Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 26, Pages 3726-3736Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100650
Keywords
Ab initio calculations; Dyes; pigments; ESIPT; Fluorescence; Salicylaldehydes
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The optical properties of synthesized salicylaldehyde derivatives were investigated, showing significant fluorescence effects in both solution and solid-state, with Excited-State Intramolecular Proton Transfer (ESIPT) fluorescence. Modifying the spacer triggered major differences in terms of maximum emission wavelength and fluorescence quantum yields in various media.
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 salicylaldehyde derivatives possessing a pi-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, KBr pellets or as powders leading to the observation of a pronounced fluorosolvatochromism. Emission wavelengths in the range 400-654 nm, along with photoluminescence quantum yields up to 76 % were recorded. Modification of the spacer (ethynyl, vinyl or direct connection) involved the pi-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.
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