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Conjugated bis(enaminones) as effective templates for rotaxane assembly and their post-synthetic modifications
- Source :
- Communications Chemistry, Vol 7, Iss 1, Pp 1-8 (2024)
- Publication Year :
- 2024
- Publisher :
- Nature Portfolio, 2024.
-
Abstract
- Abstract The development of efficient methods for the synthesis of mechanically interlocked compounds is currently considered a major challenge in supramolecular chemistry. Twofold vinylogous fumaramides, a class of conjugated bis(enaminones), successfully achieve the assembly of hydrogen-bonded amide-based rotaxanes, with a templating ability comparable to that of their parent fumaramide-based systems, showcasing full conversions and impressive yields up to 92%. Computational calculations offer a compelling explanation for the remarkable efficiency of these bis(enaminones) in driving the synthesis of unprecedented rotaxanes. The reactivity of these interlocked species was thoroughly investigated, revealing that a one-step double stopper-exchange process can be successfully performed while preserving the mechanical bond. This approach facilitates the formation of controllable rotaxanes, including a three-station molecular shuttle, whose assembly via a clipping methodology is highly unselective. The internal translational motion of this latter species has been successfully controlled in a reversible way by means of a cycloaddition/retrocycloaddition sequence.
Details
- Language :
- English
- ISSN :
- 23993669
- Volume :
- 7
- Issue :
- 1
- Database :
- Directory of Open Access Journals
- Journal :
- Communications Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.9062272259fd4695b66dc6d3bea24172
- Document Type :
- article
- Full Text :
- https://doi.org/10.1038/s42004-024-01258-4