Design, synthesis, and properties of a six-membered oligofuran macrocycle. Issue 8 (22nd February 2021)

• Record Type: Journal Article
• Authors: Varni, Anthony J.; Kawakami, Manami; Tristram-Nagle, Stephanie A.; Yaron, David; Kowalewski, Tomasz; Noonan, Kevin J. T.
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 8(2021)
• Page Start: 1775
• Page End: 1782
• Publication Date: 2021-02-22
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00084e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : In this report, the synthesis and properties of an ester-functionalized macrocyclic sexifuran (C6FE) are presented. Abstract : 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.