Synthesis of Ring-Locked Tetracyclic Dithienocyclopentapyrans and Dibenzocyclopentapyran via 1,5-Hydride Shift and Copper-Catalyzed C–O Bond Formation for Nonfullerene Acceptors
| Autor: | Yen-Ju Cheng, Santosh K. Sahoo, Hsiao Chieh Chou, Fong Yi Cao, Chia Wei Wang, Wen Ching Yin, Tze Gang Hsu, Ching Li Huang, Shao Ling Chang |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Hydride Organic Chemistry Bond formation 010402 general chemistry Cyclopentanone Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Yield (chemistry) Moiety Physical and Theoretical Chemistry Isomerization |
| Zdroj: | Organic Letters. 23:1692-1697 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c00110 |
| Popis: | 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%. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|