Self-Assembly of Stimuli-Responsive [2]Rotaxanes by Amidinium Exchange

• DOI: 10.1021/jacs.1c05230
• Publication Date: 2021-09-24T18:20:57Z
• Authors: Oleg Borodin; Yevhenii Shchukin; Craig C. Robertson; Stefan Richter; Max von Delius
• Keywords: Rotaxane; Dynamic Covalent Chemistry; Moiety; Catenane

Advances in supramolecular chemistry are often underpinned by the development of fundamental building blocks and methods enabling their interconversion. In this work, we report use an underexplored dynamic covalent reaction for synthesis stimuli-responsive [2]rotaxanes. The formamidinium moiety lies at heart these mechanically interlocked architectures, because it enables both exchange binding simple crown ethers. We demonstrated that rotaxane self-assembly follows a unique pathway complex interplay between ether thread can be controlled transient fashion addition base fuel acid. Dynamic combinatorial libraries, when exposed to diverse nucleophiles, revealed profound stabilizing effect mechanical bond as well intriguing reactivity differences seemingly similar