Active metal template synthesis of rotaxanes from BINOL-phosphate macrocycles

2025/11/11 by Nikolai Brodt, Jan Riebe, Adrian Bialowons +4 · 1 voice
Chemistry · Materials Science · #Dendrimers and Hyperbranched Polymers #Supramolecular Chemistry and Complexes #Synthesis and Properties of Aromatic Compounds

paper · doi:10.26434/chemrxiv-2025-6vtwz

openalex created_date 2025/11/11 · openalex publication_date 2025/11/11 · openalex updated_date 2026/08/01

Abstract

A new active metal template synthesis of [2]rotaxanes is described. We demonstrate the use of macrocyclic BINOL-phosphates as ligands for the Cu(I)-mediated alkyne-azide cycloaddition, establishing a mechanical bond. The influence of thread length and macrocycle size was investigated in detail and different chiral rotaxanes could be isolated in good yields. In addition, we found that functionalized alkynes, featuring hydroxyl- or amino-groups, were well-tolerated. This work not only delivers a generally applicable active template method for generating BINOL-phosphate containing rotaxanes, but also represents the first active metal template approach without nitrogen-based donors in the macrocycle.

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