Hydrofuran ring-fused calix[4]pyrrole: synthesis and ion-binding studies

A hydrofuran-fused calix[4]pyrrole (2) was synthesised from the condensation of pyrrole with acetone (0.75 equiv.) and hydroxyacetone (0.25 equiv.) in the presence of 1.0 equiv. of methanesulphonic acid. In analogy to what was seen with normal calix[4]pyrrole (1), 1 H NMR spectroscopic and isotherma...

Full description

Saved in:
Bibliographic Details
Published in:Supramolecular chemistry 2012-07, Vol.24 (7), p.481-486
Main Authors: Kim, Sung Kuk, Yeon, Yerim, Gross, Dustin E., Sessler, Jonathan L.
Format: Article
Language:English
Subjects:
anion recognition
calixpyrroles
Chemistry
heterocycles
ion pair
supramolecular chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A hydrofuran-fused calix[4]pyrrole (2) was synthesised from the condensation of pyrrole with acetone (0.75 equiv.) and hydroxyacetone (0.25 equiv.) in the presence of 1.0 equiv. of methanesulphonic acid. In analogy to what was seen with normal calix[4]pyrrole (1), 1 H NMR spectroscopic and isothermal titration calorimetry analyses served to confirm that compound 2 can act as an effective receptor for anions, such as the halides and benzoate. In addition, compound 2 was found to solubilise CsF in chloroform more effectively than calix[4]pyrrole 1, a finding attributed to participation of the oxygen atom of 2 in the caesium cation complexation process.
ISSN:1061-0278
1029-0478
DOI:10.1080/10610278.2012.688971