Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges

Yu Chieh Pao; Yung Lung Chen; Yen Ting Chen; Sheng Wen Cheng; Yu Ying Lai; Wen Chia Huang; Yen-Ju Cheng

doi:10.1021/ol502793e

Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges

Yu Chieh Pao, Yung Lung Chen, Yen Ting Chen, Sheng Wen Cheng, Yu Ying Lai, Wen Chia Huang, Yen-Ju Cheng^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	5724-5727
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol502793e
State	Published - 7 Nov 2014

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title = "Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges",

abstract = "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.",

author = "Pao, {Yu Chieh} and Chen, {Yung Lung} and Chen, {Yen Ting} and Cheng, {Sheng Wen} and Lai, {Yu Ying} and Huang, {Wen Chia} and Yen-Ju Cheng",

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doi = "10.1021/ol502793e",

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journal = "Organic Letters",

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T1 - Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges

AU - Pao, Yu Chieh

AU - Chen, Yung Lung

AU - Chen, Yen Ting

AU - Cheng, Sheng Wen

AU - Lai, Yu Ying

AU - Huang, Wen Chia

AU - Cheng, Yen-Ju

PY - 2014/11/7

Y1 - 2014/11/7

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges

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