Hydroxy Groups Enhance [2]Rotaxane Anion Binding Selectivity.

ABSTRACT: We report the synthesis of two [2]rotaxanes containing an interlocked three dimensional binding cavity formed from a pyridinium bis(amide) axle component containing two phenol donors, and an isophthalamide based macrocycle. In the competitive solvent mixture 1 : 1 CDCl₃  : CD₃ OD, one of the receptors exhibits a much higher selectivity preference for chloride than an analogous rotaxane without the hydroxy groups. X-ray crystal structures reveal the chloride anion guest encapsulated within the interlocked binding cavity, though not all of the hydrogen bond donors are utilised. Computational semi-empirical simulations indicate that secondary intermolecular interactions occur between the axle hydroxy hydrogen bond donors and the [2]rotaxane macrocycle components, contrib

SUBMITTER: Goodwin RJ 

PROVIDER: S-EPMC9321576 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature