TY  - JOUR
A1  - Wessig, Pablo
A1  - John, Leonard
A1  - Sperlich, Eric
A1  - Kelling, Alexandra
T1  - Sulfur tuning of [1,3]-dioxolo[4.5-f]benzodioxole (DBD) fluorescent dyes
T2  - European journal of organic chemistry
N2  - 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 S-4-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 (S-1-DBD, 1,2-S-2-DBD, and 1,4-S-2-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 S-1- and S-2-DBD dyes is improved, compared with S-4-DBD dyes. For coupling with biomolecules a series of reactive derivatives of the new dyes were developed (azides, OSu esters, alkynes, maleimides).
KW  - fluorescent dyes
KW  - heterocycles
KW  - photophysics
KW  - stokes shift
KW  - sulfur
Y1  - 2020
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/56623
SN  - 1434-193X
SN  - 1099-0690
VL  - 2021
IS  - 3
SP  - 499
EP  - 511
PB  - Wiley-VCH
CY  - Weinheim
ER  -