P. Wessig, L. John, E. Sperlich, A. Kelling
Sulfur Tuning of [1,3]-dioxolo[4.5-f]benzodioxole (DBD) Fluorescent Dyes
Eur. J. Org. Chem. 2021, 499-511
DOI: 10.1002/ejoc.202001418
The replacement of oxygen by sulfur atoms of [1,3]-dioxolo[4.5-f]benzodioxole (DBD) fluorescent dyes is an efficient way to adjust the photophysical properties (sulfur tuning). While previously developed S4-DBD dyes exhibit considerably red-shifted absorption and emission wavelength, the heavy atom effect of four sulfur atoms cause low fluorescence quantum yields and short fluorescence lifetimes. Herein we demonstrate that the replacement of less than four sulfur atoms (S1-DBD, 1,2-S2-DBD, and 1,4-S2-DBD dyes) permits a fine-tuning of the photophysical properties. In some cases, a similar influence on the wavelength without the detrimental effect on the quantum yields and lifetimes is observed. Furthermore, the synthetic accessibility of S1- and S2-DBD dyes is improved, compared with S4-DBD dyes. For coupling with biomolecules a series of reactive derivatives of the new dyes were developed (azides, OSu esters, alkynes, maleimides).
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