Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 1, Pages 448-454Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403853
Keywords
analytical methods; anion-pi interactions; hydrogen bonding; ion-selective electrode; nanotubes
Categories
Funding
- Spanish Ministerio de Economia y Competitividad [CTQ2010-18717, CTQ2011-23014]
- ICIQ Foundation
- Generalitat de Catalunya [2009SGR00686]
- Universitat Rovira i Virgili
- Institute of Chemical Research of Catalonia [095.002 ICIQ-URV]
- ICREA Funding Source: Custom
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The performance of chloride-selective electrodes based on two-wall aryl-extended calix[4] pyrroles and multiwall carbon nanotubes is presented. The calix[4] pyrrole receptors bear two phenyl groups at opposite meso-positions. When the meso-phenyl groups are decorated with strong electron-withdrawing substituents, attractive anion-pi interactions may exist between the receptor's aromatic walls and the sandwiched anion. These anion-pi interactions are shown to significantly affect the selectivity of the electrodes. Calix[4] pyrrole, bearing a p-nitro withdrawing group on each of the meso-phenyl rings, afforded sensors that display anti-Hofmeister behavior against the lipophilic salicylate and nitrate anions. Based on the experimental data, a series of principles that help in predicting the suitability of synthetic receptors for use as anion-specific ionophores is discussed. Finally, the sensors deliver excellent results in the direct detection of chloride in bodily fluids.
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