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 =...
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2025
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| Zusammenfassung: | 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. |
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