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

Overview

Journal Chemistry

Specialty Chemistry

Date 2024 Sep 4

PMID 39231129

Authors

Arya Arun

Andrew Docker

Paul D Beer

Affiliations

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Abstract

The first examples of bis-squaramide axle containing [2]rotaxanes linked via rigid aryl and flexible alkyl spacers synthesised using copper(I) catalysed active metal template methodology are reported. The halide and oxoanion binding properties of the [2]rotaxanes in aqueous-organic solvent media are examined through extensive H-NMR titration experiments to investigate the impact of integrating multiple squaramide motifs on the anion binding capabilities of the interlocked receptors. These studies reveal that the bis-squaramide rotaxane host systems exhibit enhanced halide anion binding capabilities relative to a mono-squaramide axle functionalised rotaxane, demonstrating a rare anti-Hofmeister bias halide anion selectivity trend in aqueous-organic mixtures and highlighting the efficacy of the potent solvent shielded hydrophobic interlocked binding pocket created upon mechanical bond formation. Notably, employing a rigid aryl linker between the two squaramide motifs in the axle component enables the rotaxane host to exhibit strong and selective binding of tetrahedral oxoanions. Conversely, a flexible alkyl spacer facilitates trigonal oxoanion selective recognition by the bis-squaramide [2]rotaxane.

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.

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