Synthesis, characterization and photophysical properties of new 2(3H) furanone derivatives

•Synthesis A new 5-aryl-3-((E)-3-phenylallylidene)-2(3H)-furanones (3a-f) compounds.•Photophysical properties of synthesized compounds have been studied.•The quantum yield and Stokes shift have been calculated.•The effect of solvent polarity on the absorption and emission spectra have been examined....

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Bibliographic Details
Published in:Journal of molecular structure 2023-02, Vol.1274, p.134543, Article 134543
Main Authors: Soliman, Mohamed H.A., El-Sakka, Sahar S., Fathy, Asmaa S., Kamel, Rasha M.
Format: Article
Language:English
Subjects:
Fluorescence
Furanone
Quantum yield
Solvatochromism
Spectroscopy
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Summary:•Synthesis A new 5-aryl-3-((E)-3-phenylallylidene)-2(3H)-furanones (3a-f) compounds.•Photophysical properties of synthesized compounds have been studied.•The quantum yield and Stokes shift have been calculated.•The effect of solvent polarity on the absorption and emission spectra have been examined. A new class of 5-aryl-3-((E)-3-phenylallylidene)-2(3H)-furanones (3a-f) derivatives was synthesised and thoroughly characterised using 1H NMR, FT-IR, and elemental analysis. The absorption and emission spectra of prepared compounds (3a-f) have been conducted in ten different solvents with different polarities. The emission spectra for all synthesized derivatives are the same in shape, with a large red shift being recorded with increasing solvent polarity. Additionally, the quantum yield decreases more than 20-fold from toluene to water. Due to the resonance structures of such derivatives, the electronegative oxygen atom in the unsaturated carbonyl fragment can form hydrogen bonds with protic solvents.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2022.134543