Hydroxy Groups Enhance [2]Rotaxane Anion Binding Selectivity

Overview

Journal Chemistry

Specialty Chemistry

Date 2022 Mar 16

PMID 35293643

Authors

Rosemary J Goodwin

Andrew Docker

Hugo I MacDermott-Opeskin

Heather M Aitken

Megan L OMara

Paul D Beer

Nicholas G White

Affiliations

Soon will be listed here.

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 CDCl : CD 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, contributing to a more preorganised binding pocket, which may be responsible for the observed enhanced selectivity.

Citing Articles

Bis-Squaramide-Based [2]Rotaxane Hosts for Anion Recognition.

Arun A, Docker A, Beer P Chemistry. 2024; 30(69):e202402731.

PMID: 39231129 PMC: 11632403. DOI: 10.1002/chem.202402731.

Determining Ion-Pair Binding Affinities of Heteroditopic Receptor Systems.

Docker A, Tay H Chemistry. 2024; 30(68):e202402844.

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Selective sodium halide over potassium halide binding and extraction by a heteroditopic halogen bonding [2]catenane.

Tay H, Docker A, Hua C, Beer P Chem Sci. 2024; 15(32):13074-13081.

PMID: 39148789 PMC: 11322978. DOI: 10.1039/d4sc03381g.

Dynamic Metalloporphyrin-Based [2]Rotaxane Molecular Shuttles Stimulated by Neutral Lewis Base and Anion Coordination.

Wilmore J, Tse Y, Docker A, Whitehead C, Williams C, Beer P Chemistry. 2023; 29(33):e202300608.

PMID: 36929530 PMC: 10947143. DOI: 10.1002/chem.202300608.

Halogen-Bonding Heteroditopic [2]Catenanes for Recognition of Alkali Metal/Halide Ion Pairs.

Tay H, Tse Y, Docker A, Gateley C, Thompson A, Kuhn H Angew Chem Int Ed Engl. 2022; 62(5):e202214785.

PMID: 36440816 PMC: 10108176. DOI: 10.1002/anie.202214785.

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