1,7-Dihalogenated BODIPYs: Synthesis, Structure and Photophysics
4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY) and its derivatives are highly useful fluorescent dyes employed in myriad applications in chemistry and biology. Here, we revisit a series of dihalogenated (Cl, Br, I) BODIPY derivatives with rare 1,7-regiochemistry. In addition to their synthesis and structural characterization, we fill in a missing piece of the current literature by delineating their photophysical behavior, including the light-driven generation of singlet oxygen (<sup>1</sup>O<sub>2</sub>) which is mediated with particularly high efficiency by the heavier diiodinated congener.
Authors
- Robert J. Ortiz (ORCID: https://orcid.org/0000-0001-9078-765X)
- J. A. Gareth Williams (ORCID: https://orcid.org/0000-0002-4688-3000)
- David E. Herbert (ORCID: https://orcid.org/0000-0001-8190-2468)
- Dion B. Nemez (ORCID: https://orcid.org/0000-0003-0410-730X)
- Amelia Kacperkiewicz (ORCID: https://orcid.org/0009-0004-3689-4250)
Institutions
- Durham University (GB)
- University of Manitoba (CA)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-22
- DOI
- https://doi.org/10.1021/acs.joc.5c00407
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Canada Foundation for Innovation
- Natural Sciences and Engineering Research Council of Canada