Issue 27, 2014

Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane

Abstract

A new rotaxane containing the 3-amido-phenyl-triazolium group incorporated into the interlocked structure's axle component has been prepared by a chloride anion templated clipping strategy. Proton NMR titration experiments reveal that the interlocked host displays a high degree of halide anion recognition in competitive 1 : 1 CDCl3–CD3OD solvent mixture. Chloride and bromide anions are bound strongly and selectively, with negligible complexation of the larger, more basic oxoanions, acetate and dihydrogen phosphate being observed. Density functional theory calculations on the related axle motifs 3-amido-phenyl-triazolium, pyridinium bis-triazole and pyridinium bis-amide were performed, and indicate that the new rotaxane axle motif displays much weaker oxoanion binding than the pyridinium based systems.

Graphical abstract: Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane

Supplementary files

Article information

Article type
Paper
Submitted
17 Apr 2014
Accepted
15 May 2014
First published
30 May 2014

Org. Biomol. Chem., 2014,12, 4924-4931

Author version available

Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane

N. G. White, A. R. Colaço, I. Marques, V. Félix and P. D. Beer, Org. Biomol. Chem., 2014, 12, 4924 DOI: 10.1039/C4OB00801D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements