Synthesis of Spiro[cyclopenta[1,2-b:5,4-b′]DiThiophene-4,9′-Fluorenes] SDTF dissymmetrically functionalized

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Recently, spiro compounds and more precisely spirobifluorene (SBF) based organic semiconductors have attracted considerable attention. In this context, the development of heterocyclic analogues of the SBF appears interesting. In this Letter, we report a strategy to prepare two selectively brominated Spiro[cyclopenta[1,2-b:5,4-b′]DiThiophene-4,9′-Fluorene] SDTF derivatives. Moreover, it is worth noting that our investigations also allowed the synthesis of an original and scantly described dispiro-oxepine motif. In order to probe the potential and the difference of properties of prepared compounds, the later have been functionalized by ethylenedioxythiophene moieties. Electrochemical and spectroscopic properties of the corresponding compounds are described herein.