Fluorescent dyes with large stokes shifts based on Benzo[1,2-d:4,5-d']bis([1,3]dithiole) (“S4-DBD Dyes”)
- 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.
Author details: | Pablo WessigORCiDGND, Daniel FreyseORCiDGND, David Schuster, Alexandra Kelling |
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DOI: | https://doi.org/10.1002/ejoc.202000093 |
ISSN: | 1434-193X |
ISSN: | 1099-0690 |
Title of parent work (English): | Europan journal of organic chemistry |
Publisher: | Wiley |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Date of first publication: | 2020/02/06 |
Publication year: | 2020 |
Release date: | 2022/11/28 |
Tag: | fluorescent dyes; heterocycles; photophysics; stokes shift; sulfur |
Volume: | 2020 |
Issue: | 11 |
Number of pages: | 13 |
First page: | 1732 |
Last Page: | 1744 |
Funding institution: | transnational E-RARE grant `CCMCURE (DFG)European Commission [SFB958]; E-RARE [ERL 138397]; Canadian; Institutes for Health ResearchCanadian Institutes of Health Research; (CIHR) [PJT 153000]; the E-RARE grant `CCMCURE |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer review: | Referiert |
Publishing method: | Open Access / Hybrid Open-Access |
License (German): | CC-BY-NC-ND - Namensnennung, nicht kommerziell, keine Bearbeitungen 4.0 International |