[2]Rotaxanes comprising a macrocylic Hamilton receptor obtained using active template synthesis: synthesis and guest complexation

Abstract

A macrocyclic ring comprising multiple hydrogen-bonding sites as well as metal-chelating sites is shown to play the role of ligand in active templated, copper-catalysed [2]rotaxane formation via Huisgen and Glaser reactions. The crystallographic structure and copper ion binding studies are provided for the free macrocycle, along with molecular modelling, barbital, N,N′-trimethyleneurea and copper (I) binding information for the new rotaxanes.

Keywords:

• Rotaxane
• activate template synthesis
• Hamilton receptor
• macrocycle
• click chemistry

Supplementary material

Supplementary data for this article can be accessed here: http://dx.doi.org/.10.1080/10610278.2015.1122194

Disclosure statement

No potential conflict of interest was reported by the authors.

Notes

1. Values determined by NMR spectroscopy in CDCl₃ at a concentration of 3.5 mM.