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

[Display omitted] •We synthesized several based thiophene heteroaromatic analogues of spirobifluorene.•Our synthetic strategy also allowed isolating a rare dispiro-oxepine derivative.•Electrochemical and spectroscopic properties of derivatives are discussed. Recently, spiro compounds and more precis...

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Bibliographic Details
Published in:Tetrahedron letters 2015-03, Vol.56 (11), p.1383-1387
Main Authors: Jeux, Victorien, Dalinot, Clément, Allain, Magali, Sanguinet, Lionel, Leriche, Philippe
Format: Article
Language:English
Subjects:
Chemical Sciences
Cyclization
Dispiro-oxepine
Electroactive polymer
Spirobifluorene
Thiophene
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Summary:[Display omitted] •We synthesized several based thiophene heteroaromatic analogues of spirobifluorene.•Our synthetic strategy also allowed isolating a rare dispiro-oxepine derivative.•Electrochemical and spectroscopic properties of derivatives are discussed. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.01.173