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Issue 5, 2017
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Functionalization of pentacene-5,7,12,14-tetraone with geminal enediyne and 1,3-dithiole groups

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Abstract

Pentacene-5,7,12,14-tetraone was subjected to selective olefination and cross-coupling reactions to yield a new class of pentacene-based π-conjugated systems functionalized with geminal enediyne and 1,3-dithiole groups. The electron donating and accepting effects of enediyne and dithiole groups render these compounds intriguing structural, electronic properties, and redox activities which were systematically investigated by UV-Vis absorption and cyclic voltammetric analyses in conjunction with density functional theory (DFT) calculations. The bis(enediyne)-substituted pentacenedione showed potential application in the preparation of carbon-rich polymeric materials.

Graphical abstract: Functionalization of pentacene-5,7,12,14-tetraone with geminal enediyne and 1,3-dithiole groups

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Publication details

The article was received on 15 Jan 2017, accepted on 20 Mar 2017 and first published on 21 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00041C
Citation: Org. Chem. Front., 2017,4, 804-810
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    Functionalization of pentacene-5,7,12,14-tetraone with geminal enediyne and 1,3-dithiole groups

    E. A. Younes and Y. Zhao, Org. Chem. Front., 2017, 4, 804
    DOI: 10.1039/C7QO00041C

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