Anion-templated assembly of [2]rotaxanes

Organic & Biomolecular Chemistry Pub Date: 2006-03-10 DOI: 10.1039/B518178J

Abstract

Anion templation is used to develop a general method for rotaxane synthesis. The anion-templated synthesis of three new [2]rotaxanes containing positively charged pyridinium axles and neutral isophthalamide macrocyclic components is described. The incorporation of electron withdrawing substituents, such as the nitro group, into the 5-position of an isophthalamide bis-vinyl acyclic precursor results in a significant improvement in [2]rotaxane assembly yields. Rotaxane anion binding strengths are also enhanced whilst the rotaxane's unique interlocked binding domain ensures selectivity for chloride – the templating anion – is maintained.

Graphical abstract: Anion-templated assembly of [2]rotaxanes
Recommended Literature