1,3-Dithiole-2-one-Fused Subphthalocyanine and Subporphyrazine: Synthesis and Properties Arising from the 1,3-Dithiole-2-one Units

Yemei Wang, Koya Uchihara, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu

    Research output: Contribution to journalArticlepeer-review

    10 Citations (Scopus)

    Abstract

    Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S 2 CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S 2 CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C 60 . Finally, using the reactivity of the peripheral S 2 CO units, S 2 CO-fused SubPc was successfully converted into tetrathiafulvalene (TTF)-annulated SubPc in a yield higher than that of the direct synthesis from a TTF-fused phthalonitrile.

    Original languageEnglish
    Pages (from-to)3103-3107
    Number of pages5
    JournalOrganic letters
    Volume21
    Issue number9
    DOIs
    Publication statusPublished - May 3 2019

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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