Fluorosolvatochromism of furanyl- and thiophenyl-substituted acetophenones

Autor: Friebe, Nadine, Schreiter, Katja, Kübel, Joachim, Dietzek, Benjamin, Moszner, Norbert, Burtscher, Peter, Oehlke, Alexander, Spange, Stefan
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: New J. Chem., 2015,39, 5171-5179
Druh dokumentu: Článek
ISSN: 1144-0546
DOI: 10.1039/C5NJ00256G
Popis: A series of para-substituted acetophenones bearing a furanyl or a thiophenyl moiety show a large Stokes-shift, which is a function of various solvent properties. Photophysical properties such as emission lifetime of the compounds have been determined using time-correlated-single photon counting to secure the intrinsic fluorescence behaviour. The solvent dependent position of the UV/Vis emission band [small nu, Greek, tilde]max,em of the compounds has been measured in 26 various solvents. The influence of the solvent on [small nu, Greek, tilde]max,em is of very complex nature and mathematically analysed by multiple square linear solvation energy (LSE)-correlation analysis using Catalán's four-solvent parameter set. Solvent acidity has a strong influence on the bathochromic shift of 2,5-disubstituted furan derivatives compared to the non-5-substituted furan and thiophene derivatives, which show a contrary behaviour. Therefore, the 5-cyanofuranyl-substituted acetophenone derivative is useful as a probe for measuring environmental properties by fluorescence spectroscopy.
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