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Fluorescent Dyes with Large Stokes Shifts Based on Benzo[1,2‐d:4,5‐d']bis([1,3]dithiole) (“S 4 ‐DBD Dyes”)
Author(s) -
Wessig Pablo,
Freyse Daniel,
Schuster David,
Kelling Alexandra
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000093
Subject(s) - intersystem crossing , chemistry , stokes shift , fluorescence , photochemistry , absorption (acoustics) , quantum yield , sulfur , wavelength , excited state , atomic physics , organic chemistry , optoelectronics , optics , physics , singlet state
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 sulfur 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 sulfur atoms. The very large Stokes shifts of the S 4 ‐DBD dyes ranging from 3000 cm –1 to 7400 cm –1 (67 nm to 191 nm) should be especially emphasized. 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.