Abstract
Although catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, we report the design and syntheses of two 3D catenanes by a sequence of SN2 reactions in one pot. The resulting triply mechanically interlocked molecules were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold symmetric cage component as the suit and a tribromide component as the body, is formed at elevated temperatures. This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodynamic minima. We foresee a future in which this particular synthetic strategy guides the rational design and production of mechanically interlocked molecules under kinetic control.
Original language | English (US) |
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Article number | e2118573119 |
Journal | Proceedings of the National Academy of Sciences of the United States of America |
Volume | 119 |
Issue number | 12 |
DOIs | |
State | Published - Mar 22 2022 |
Keywords
- Cationic cages
- Mechanically interlocked molecules
- Nontrivial topologies
- Suitanes
- Triple [π...π] interactions
ASJC Scopus subject areas
- General
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CCDC 2114508: Experimental Crystal Structure Determination
Wu, Y. (Contributor), Guo, Q. (Contributor), Qiu, Y. (Contributor), Weber, J. A. (Contributor), Young, R. M. (Contributor), Bancroft, L. (Contributor), Jiao, Y. (Contributor), Chen, H. (Contributor), Song, B. (Contributor), Liu, W. (Contributor), Feng, Y. (Contributor), Zhao, X. (Contributor), Li, X. (Contributor), Zhang, L. (Contributor), Chen, X. (Contributor), Li, H. (Contributor), Wasielewski, M. R. (Contributor) & Stoddart, J. F. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc28z9yj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc28z9yj&sid=DataCite
Dataset
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CCDC 2114509: Experimental Crystal Structure Determination
Wu, Y. (Contributor), Guo, Q. (Contributor), Qiu, Y. (Contributor), Weber, J. A. (Contributor), Young, R. M. (Contributor), Bancroft, L. (Contributor), Jiao, Y. (Contributor), Chen, H. (Contributor), Song, B. (Contributor), Liu, W. (Contributor), Feng, Y. (Contributor), Zhao, X. (Contributor), Li, X. (Contributor), Zhang, L. (Contributor), Chen, X. (Contributor), Li, H. (Contributor), Wasielewski, M. R. (Contributor) & Stoddart, J. F. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc28z9zk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc28z9zk&sid=DataCite
Dataset