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Issue 42, 2014
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Polymerisable squaramide receptors for anion binding and sensing

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Abstract

A novel series of polymerisable squaramides has been synthesised in high yields using simple chemical reactions, and evaluated in the binding of anionic species. These vinyl monomers can be used as functional building blocks in co-polymerisations with a plethora of co-monomers or cross-linkers, grace to their compatibility with free-radical polymerisation reactions. Aromatic substituted squaramides were found to be the strongest receptors, while binding of certain anions was accompanied by a strong colour change, attributed to the de-protonation of the squaramide. The best performing squaramide monomers were incorporated in molecularly imprinted polymers (MIPs) targeting a model anion and their capacities and selectivity were evaluated by rebinding experiments. Polymers prepared using the new squaramide monomers were compared to urea based co-polymers, and were found to contain up to 80% of the theoretical maximum number of binding sites, an exceptionally high value compared to previous reports. Strong polymer colour changes were observed upon rebinding of certain anions, equivalent to those witnessed in solution, paving the way for application of such materials in anion sensing devices.

Graphical abstract: Polymerisable squaramide receptors for anion binding and sensing

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Supplementary files

Article information


Submitted
10 Aug 2014
Accepted
18 Sep 2014
First published
19 Sep 2014

This article is Open Access

J. Mater. Chem. C, 2014,2, 8990-8995
Article type
Paper
Author version available

Polymerisable squaramide receptors for anion binding and sensing

P. Manesiotis, A. Riley and B. Bollen, J. Mater. Chem. C, 2014, 2, 8990
DOI: 10.1039/C4TC01776E

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