Fluorosolvatochromism of furanyl- and thiophenyl-substituted acetophenones


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.

acetophenone derivative, furan derivative, solvent, thiophene derivative, acidity, correlation analysis, fluorescence spectroscopy, lifespan, substitution reaction, ultraviolet radiation
Friebe, N., Schreiter, K., Kübel, J., Dietzek, B., Moszner, N., Burtscher, P., et al. (2015). Fluorosolvatochromism of furanyl- and thiophenyl-substituted acetophenones (Version publishedVersion, Vol. 39). Version publishedVersion, Vol. 39. London : RSC. https://doi.org//10.1039/c5nj00256g