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

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...

A pyridine-N-oxide catenane for cation recognition

“…Hydrogen bonding – often augmented with other non-covalent interactions – has been widely used in the templated synthesis of mechanically interlocked molecules (MIMs) 1 such as catenanes 2 and rotaxanes. 3 Examples of MIMs prepared by hydrogen bonding templation strategies, 4,5 have been explored as nanotechnological components such as molecular switches 6 and rotors, 7 as well as catalysts 8 and receptors for anionic guests. 9…”

Rapid synthesis of hydrogen bond templated handcuff rotaxanes

“…6a,d,e Our group has reported on the rapid synthesis of [2]rotaxanes by copper catalyzed azide-alkyne cycloaddition (CuAAC) stoppering of a hydrogen bond templated pseudorotaxane consisting of a simple aromatic amide azide threading through an isophthalamide macrocycle. 10,11 We envisioned that adapting such a methodology by use of an analogous bis-macrocycle and a bis-alkyne rather than an alkyne stopper could afford (2)handcuff [2]rotaxanes in a short synthetic pathway (Fig. 1).…”