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

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 cyclopentanon...

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Bibliographic Details
Published in:Organic letters 2021-03, Vol.23 (5), p.1692-1697
Main Authors: Hsu, Tze-Gang, Huang, Ching-Li, Yin, Wen-Ching, Cao, Fong-Yi, Wang, Chia-Wei, Sahoo, Santosh K, Chang, Shao-Ling, Chou, Hsiao-Chieh, Cheng, Yen-Ju
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Language:English
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Summary: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%.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00110