Hydrogen bond templated synthesis of catenanes and rotaxanes from a single isophthalic acid derivative

Barlow, Sean R. and Akien, Geoffrey R. and Evans, Nicholas H. (2023) Hydrogen bond templated synthesis of catenanes and rotaxanes from a single isophthalic acid derivative. Organic and Biomolecular Chemistry, 21 (2). pp. 402-414. ISSN 1477-0520

Abstract

Hydrogen bond templated [2]catenanes and [2]rotaxanes have been synthesized using azide precursors derived from a single isophthalic acid derivative precursor. The interlocked molecules were prepared using either stoichiometric or near stoichiometric amounts of macrocycle and CuAAC "click" precursors, with yields of up to 70% for the mechanical bond formation step. Successful preparation of the interlocked structures was confirmed by NMR spectroscopy and mass spectrometry, with detail of co-conformational behaviour being elucidated by a range of H NMR spectroscopic experiments.