Synthesis, spectroscopic characterization and photophysics of new functionalized 2,3-distyrylfurans

Substituent and solvent effects on their photobehavior

Irena Škorić, Ilijana Kikaš, Margit Kovács, Marija Šindler-Kulyk, O. Horváth

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Two new groups of p-chloro-, p-methoxy- and p-nitro-substituted derivatives of the trans,trans-isomers of 2,3-distyrylfuran have been synthesized by a sequence of reactions according to known methods. These new conjugated heterocyclic compounds along with the parent one and its methyl-derivative have been characterized spectrally, photophysically and photochemically. These compounds, except for the nitro-derivatives, display high fluorescence quantum yields in the non-polar n-hexane (ΦF=0.76-0.98). In ethanol of high polarity, the lifetime of their singlet excited state increases from 1.31-2.59ns to 2.01-4.77ns, significantly enhancing the quantum yield of their photochemical reaction from 0.02-0.24 to 0.25-0.46, and diminishing their fluorescence efficiency (ΦF=0.26-0.64). Deviating from the other compounds studied, the quantum yields for both the fluorescence and the photolysis of the nitro-derivatives are rather low (ΦF-4, Φ=0.025-0.042 in ethanol), probably due to an efficient intersystem crossing leading to a non-reactive triplet state. Accordingly, their singlet-state lifetime is also relatively short (τF

Original languageEnglish
Pages (from-to)152-161
Number of pages10
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume211
Issue number2-3
DOIs
Publication statusPublished - Apr 2010

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Quantum yield
Derivatives
fluorescence
Fluorescence
ethyl alcohol
synthesis
heterocyclic compounds
life (durability)
Ethanol
Nitro Compounds
Heterocyclic Compounds
photochemical reactions
atomic energy levels
photolysis
Photochemical reactions
polarity
Photolysis
isomers
Hexane
Excited states

Keywords

  • Distyrylfuran
  • Fluorescence
  • Oxygen heterocycles
  • Photophysics
  • Solvent effect
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Cite this

Synthesis, spectroscopic characterization and photophysics of new functionalized 2,3-distyrylfurans : Substituent and solvent effects on their photobehavior. / Škorić, Irena; Kikaš, Ilijana; Kovács, Margit; Šindler-Kulyk, Marija; Horváth, O.

In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 211, No. 2-3, 04.2010, p. 152-161.

Research output: Contribution to journalArticle

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