Synthesis and Molecular Properties of Tricyclic Biselenophene-Based Derivatives with Nitrogen, Silicon, Germanium, Vinylidene, and Ethylene Bridges

A new class of biselenophene-based materials including an sp3-silicon-bridged diselenosilole (DSS), an sp3-germanium-bridged diselenogermole (DSG), and an sp3-nitrogen-bridged diselenopyrrole (DSP) as well as an sp2-vinylidene-bridged dicyano­diseleno­fulvene (CDSF), a diacetylene­diseleno­fulvene (...

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Bibliographic Details
Published in:Organic letters 2014-11, Vol.16 (21), p.5724-5727
Main Authors: Pao, Yu-Chieh, Chen, Yung-Lung, Chen, Yen-Ting, Cheng, Sheng-Wen, Lai, Yu-Ying, Huang, Wen-Chia, Cheng, Yen-Ju
Format: Article
Language:English
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Summary:A new class of biselenophene-based materials including an sp3-silicon-bridged diselenosilole (DSS), an sp3-germanium-bridged diselenogermole (DSG), and an sp3-nitrogen-bridged diselenopyrrole (DSP) as well as an sp2-vinylidene-bridged dicyano­diseleno­fulvene (CDSF), a diacetylene­diseleno­fulvene (ADSF), and a dioctyl­ethylene-bridged benzo­diseleno­phene (BDS) have been successfully synthesized and characterized. The bridging moieties play an important role in determining the optical and electrochemical properties. The six brominated derivatives are ready to construct various biselenophene-based conjugated materials with tunable properties for organic photovoltaics and field effect transistors.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502793e