Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors

Tze Gang Hsu, Ching Li Huang, Wen Ching Yin, Fong Yi Cao, Chia Wei Wang, Santosh K. Sahoo, Shao Ling Chang, Hsiao Chieh Chou, Yen-Ju Cheng*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    Abstract

    We discovered a unique synthetic route to construct 2H-pyran-containing tetracyclic dithienocyclopentapyran (DTCP) and dibenzocyclopentapyran (DBCP) architectures. The synthesis involves an acid-induced dehydration cyclization followed by a [1,5] hydride-shift isomerization to form a cyclopentanone moiety which was converted to the pyran-embedded tetracyclic products by a CuI-catalyzed intramolecular C-O bond formation in good yield. DTCP was used as a building block to prepare an acceptor-donor-acceptor (A-D-A) type n-type material DTCP-BC leading to a solar cell efficiency of 9.32%.

    Original languageEnglish
    Pages (from-to)1692–1697
    Number of pages6
    JournalOrganic Letters
    DOIs
    StatePublished - 5 Mar 2021

    Fingerprint

    Dive into the research topics of 'Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C-O Bond Formation for Nonfullerene Acceptors'. Together they form a unique fingerprint.

    Cite this