N-Methyl-2-(4-nitrophenyl)ethanamine hydrochloride (1:1)
CAS Number:
166943-39-1
Molecular Formula:
C9H13ClN2O2
Design, synthesis, and properties of a six-membered oligofuran macrocycle
Literature Information
Publication Date
2021-02-22
DOI
10.1039/D1QO00084E
Impact Factor
5.281
Authors
Anthony J. Varni, Manami Kawakami, Stephanie A. Tristram-Nagle, David Yaron, Tomasz Kowalewski, Kevin J. T. Noonan
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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