P. Wessig, D. Freyse, D. Schuster, A. Kelling
Fluorescent Dyes with Large Stokes Shifts Based on Benzo[1,2-d:4,5-d´]bis([1,3]dithiole) ("S4-DBD Dyes")
Eur. J. Org. Chem. 2020, 1732-1744
DOI: 10.1002/ejoc.202000093
We report on a further development of [1,3]-dioxolo[4.5-f]benzodioxole (DBD) fluorescent dyes by replacement of the four oxygen atoms of the heterocyclic core by sulphur atoms. This variation causes striking changes of the photophysical properties. Whereas absorption and emission significantly shifted to longer wavelength, the fluorescence lifetimes and quantum yields are diminished compared to DBD dyes. The latter effect is presumably caused by an enhanced intersystem crossing to the triplet state due to the sulphur atoms. Especially to be emphasized are the very large Stokes shifts of the S4-DBD dyes. By analogy with DBD dyes a broad variation of absorption and emission wavelength is possible by introducing different electron withdrawing substituents. Moreover, some derivatives for coupling with biomolecules were developed.
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