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

doi:10.1021/acs.orglett.1c00110

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

Org Lett. 2021 Mar 5;23(5):1692-1697. doi: 10.1021/acs.orglett.1c00110. Epub 2021 Feb 23.

Authors

Tze-Gang Hsu^{1

2}, Ching-Li Huang^{1

2}, Wen-Ching Yin^{1

2}, Fong-Yi Cao^{1

2}, Chia-Wei Wang^{1

2}, Santosh K Sahoo^{1

2}, Shao-Ling Chang^{1

2}, Hsiao-Chieh Chou^{1

2}, Yen-Ju Cheng^{1

2}

Affiliations

¹ Department of Applied Chemistry and Center for Emergent Functional Matter Science, National Yang Ming Chiao Tung University, Hsinchu 30010, Taiwan.
² Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan.

PMID: 33621105
DOI: 10.1021/acs.orglett.1c00110

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%.

Publication types

Research Support, Non-U.S. Gov't