| Autor: |
Kevin J. T. Noonan, David Yaron, Manami Kawakami, Anthony J. Varni, Stephanie Tristram-Nagle, Tomasz Kowalewski |
| Rok vydání: |
2021 |
| Předmět: |
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| Zdroj: |
Organic Chemistry Frontiers. 8:1775-1782 |
| ISSN: |
2052-4129 |
| Popis: |
Herein, we present the synthesis and properties of an ester-functionalized macrocyclic sexifuran (C6FE). This molecule was prepared in a single step from a furan-3-carboxylate dimer using a commercially available palladium catalyst (SPhos-Pd-G3) and isolated in 34% yield. DFT calculations predict the macrocyclic ring is planar, with minimal ring strain. The macrocycle is partially crystalline, as evidenced by powder X-ray diffraction patterns. Furthermore, the solid-state organization can be altered by modification of the ester side-chain. C6FE can also undergo two electron oxidation and reduction in solution as evidenced by cyclic voltammetry. Quantum chemical investigations revealed how aromaticity along the entire sexifuran macrocycle may play a role in the reversible electrochemistry. Overall, we anticipate that the synthetic approach detailed in this report can serve as a foundation to construct new furan-based conjugated macrocycles. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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