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Synthesis of Nonplanar Push–Pull Chromophores with Various Heterocyclic Moieties via [2 + 2] Cycloaddition-Retroelectrocyclization Reaction
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    Synthesis of Nonplanar Push–Pull Chromophores with Various Heterocyclic Moieties via [2 + 2] Cycloaddition-Retroelectrocyclization Reaction
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    • Xu Chen
      Xu Chen
      Department of Materials Science and Engineering, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
      More by Xu Chen
    • Tsuyoshi Michinobu*
      Tsuyoshi Michinobu
      Department of Materials Science and Engineering, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
      *Email: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 4, 1561–1570
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    https://doi.org/10.1021/acs.joc.4c02595
    Published January 16, 2025
    Copyright © 2025 American Chemical Society

    Abstract

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    A series of 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivatives with various heterocyclic moieties, including pyridine, carbazole, indole, and benzothiadiazole, was newly synthesized through a [2 + 2] cycloaddition-retroelectrocyclization reaction. Symmetric electron-rich 1,3-butadiynes with end-capped heterocyclic substituents were reacted with tetracyanoethylene (TCNE), yielding the target TCBD products in 60–80% yields under ambient or mild heating conditions. The thermal stability and optical and electrochemical properties of both 1,3-butadiyne precursors and the corresponding TCBD derivatives were investigated by using thermogravimetric analysis (TGA), UV–vis spectroscopy, and cyclic voltammetry (CV). The TCBD derivatives featured narrow bandgaps due to the intramolecular charge transfer interactions of push–pull chromophores. In addition, the optimized structures and frontier molecular orbitals with their energy levels were determined by density functional theory (DFT) calculations.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02595.

    • NMR spectra, HRMS spectra, computational calculations, and X-ray crystallographic data (PDF)

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    Deposition Number 2380282 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 4, 1561–1570
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02595
    Published January 16, 2025
    Copyright © 2025 American Chemical Society

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