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Issue 42, 2012
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Inversion of selectivity in anion recognition with conformationally blocked calix[4]pyrroles

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Abstract

Two calixpyrrole derivatives were synthesised. A p-dimethylaminobenzoyl group was electronically attached to a pyrrole ring, establishing an intramolecular hydrogen bond in a 1,3-alternate conformation. The formation of the H-bond was corroborated by IR, NMR, and X-ray measurements. NMR titration studies reveal that the H-bond is strong enough to block the conversion to a cone conformation, allowing them to only acquire a partial cone conformation. Affinity constants for several anions were calculated, and a noticeable increase was observed for tridentate tetrahedral anions, while the Ka of spheric or bidentate anions decreased. In the presence of several acids, the synthesised compounds can act as chemosensors by a double process: protonation of the amino group and coordination of the generated anion. In addition, a displacement approach gives rise to a proof of concept for sulphonate recognition.

Graphical abstract: Inversion of selectivity in anion recognition with conformationally blocked calix[4]pyrroles

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Publication details

The article was received on 09 Jul 2012, accepted on 06 Sep 2012 and first published on 07 Sep 2012


Article type: Paper
DOI: 10.1039/C2OB26309B
Citation: Org. Biomol. Chem., 2012,10, 8445-8451
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    Inversion of selectivity in anion recognition with conformationally blocked calix[4]pyrroles

    R. Gotor, A. M. Costero, S. Gil, M. Parra, L. E. Ochando and K. Chulvi, Org. Biomol. Chem., 2012, 10, 8445
    DOI: 10.1039/C2OB26309B

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