Structural Expansion of Dibenzo[<i>b</i>,<i>d</i>]thiophene Sulfone through Functionalization at Bay Positions
We report a synthesis of 1,9-dibromodibenzo[<i>b</i>,<i>d</i>]thiophene sulfone, which was converted to a respective dilithio intermediate. Subsequent trapping with electrophiles afforded either 1-substituted (R = CHO, B(OH)<sub>2</sub>) or 1,9-disubstituted (R = CO<sub>2</sub>H, I) derivatives, indicating an effect of steric factors on the outcome of this reaction. Various annulation reactions were also probed giving rise to extended π-conjugated systems. The electronic and optical properties of all compounds were characterized by cyclic voltammetry, UV-vis spectroscopy, and DFT calculations.
Authors
- Włodzimierz Buchowicz (ORCID: https://orcid.org/0000-0002-1832-7461)
- Krzysztof Durka (ORCID: https://orcid.org/0000-0002-6113-4841)
- Sergiusz Luliński (ORCID: https://orcid.org/0000-0002-9635-5572)
- J. Adámek
- Zuzanna Spychalska
Institutions
- Warsaw University of Technology (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-12
- DOI
- https://doi.org/10.1021/acs.orglett.5c02414
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Narodowe Centrum Nauki