Synthesis of a Strapped Calix[4]pyrrole: Structure and Anion Binding Properties

Synthesis of a Strapped Calix[4]pyrrole: Structure and Anion Binding Properties

Enhanced affinity and selectivity for halide anions is seen for the strapped calix[4]pyrrole (see picture, X−=F−, Cl−) relative to normal calix[4]pyrroles. The encapsulated binding site differentiates the anions on the basis of size, and the existence of hydrogen‐bonding interactions between the aro...

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Veröffentlicht in:Angewandte Chemie International Edition 2002-05, Vol.41 (10), p.1757-1759
Hauptverfasser: Yoon, Dae-Wi, Hwang, Hoon, Lee, Chang-Hee
Format: Artikel
Sprache:eng
Schlagworte:
anions
Anions - chemistry
Calixarenes - chemical synthesis
Calixarenes - chemistry
calixpyrroles
Chemistry, Organic - methods
Chlorides - chemistry
Fluorides - chemistry
Hydrogen Bonding
hydrogen bonds
Kinetics
macrocycles
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Conformation
molecular recognition
Porphyrins - chemical synthesis
Porphyrins - chemistry
Protein Binding
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Zusammenfassung:Enhanced affinity and selectivity for halide anions is seen for the strapped calix[4]pyrrole (see picture, X−=F−, Cl−) relative to normal calix[4]pyrroles. The encapsulated binding site differentiates the anions on the basis of size, and the existence of hydrogen‐bonding interactions between the aromatic proton and halide anions has been verified by 1H NMR spectroscopy. A binding constant of approximately 3.87×106 M was found for the fluoride complex.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020517)41:10<1757::AID-ANIE1757>3.0.CO;2-0