Solvatofluorochromic properties of sulfonyl fluoride derivatives of 5-aryl(heteroaryl)-2-phenyl-1,3,4-oxadiazole, promising fluorescent probes

Abstract

The spectral characteristics of seven 5-aryl(heteroaryl)-2-phenyl-1,3,4-oxadiazole derivatives, containing an expressed electron-accepting grouping such as sulfonyl fluoride or sulfonyldifluoromethane in the para position of the phenyl substituent, have been investigated in solvents of various polarity. The insignificant effect of the nπ^* levels of the SO₂X grouping on the fluorescence properties of the compounds studied was established, as a result of which they are highly effective organic luminophors in the near ultraviolet and violet spectral ranges. The presence was shown of a significant solvatochromic effect exerted particularly clearly in derivatives with electron-donating groups in the 5-aryl substituent. As a result of this, the compounds indicated may be recommended for use as fluorescent probes in medicine and biology. Adiabatic flattening in the excited state of the sterically hindered methoxy derivative and the formation of a TICT state are considered, leading to quenching of the fluorescence of dimethylamino derivatives in media of high polarity.

How to Cite
Doroshenko, A. O.; Skripkina, V. T.; Posokhov, E. A.; Obukhova, E. N.; Shershukov, V. M. Chem. Heterocycl. Compd. 1997, 33, 865. [Khim. Geterotsikl. Soedin. 1997, 988.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02253043