Issue 35, 2022

Amidosquaramides – a new anion binding motif with pH sensitive anion transport properties

Abstract

Stimuli responsive anion transport is becoming an important aspect of supramolecular anion recognition chemistry. Herein, we report the synthesis of a family of anion receptors that incorporate a new anion binding motif, amidosquaramides. We show using experimental and computational methods that these receptors have pKa values close to physiological pH but also display intramolecular H-bonding interactions that affect anion recognition. Moreover, moderate activity in a Cl/NO3 exchange assay is observed at physiological pH that can be effectively ‘switched on’ when repeated under acidic conditions. The reported findings provide synthetic methods that can be used for the construction of more complex squaramide based anion receptors and also provide insight into the importance of conformational analysis when considering receptor design.

Graphical abstract: Amidosquaramides – a new anion binding motif with pH sensitive anion transport properties

Supplementary files

Article information

Article type
Paper
Submitted
30 Jun 2022
Accepted
03 Aug 2022
First published
09 Aug 2022
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2022,20, 7056-7066

Amidosquaramides – a new anion binding motif with pH sensitive anion transport properties

L. A. Marchetti, T. Krämer and R. B. P. Elmes, Org. Biomol. Chem., 2022, 20, 7056 DOI: 10.1039/D2OB01176J

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements