Ring size is a critically important parameter in many interlocked molecules as it directly impacts their unique molecular motions. In this talk, the synthesis and characterization of numerous structurally different doubly threaded [3]rotaxanes with large macrocycles (40-46 atoms) derived from the 2,6-bis(N-alkyl-benzimidazolyl)pyridine ligand will be described. Structural features such as stopper group size, arm length, and ring size were systematically varied resulting in drastic differences in [3]rotaxane stability. For example, using a large 46 atom ditopic macrocycle, metastable rotaxanes have been accessed with room temperature stability that can be varied between a half-life of &lt; 1 minute to ca. 6 months, depending on the nature of the stopper. Fully stable [3]rotaxanes could be accessed using a 42 atom macrocycle highlighting the importance of balancing ring and stopper size. These [3]rotaxanes open the door to the development of a range of relatively long lived metastable and fully stable doubly threaded polyrotaxane networks/slide ring gels.

Controlling the stability of doubly threaded [3]rotaxanes with big rings through component design

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ACS Fall 2022

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