Issue 16, 2005

Polyaza metacyclophanes as ditopic anion receptors

Abstract

Five macrocyclic polyaza metacyclophanes L1–L5 prepared by dipode coupling of the tosylated precursors have been studied. The basicity of the ligands has been measured potentiometrically and their ability to complex halides and perchlorate has been studied in the solid state by X-ray crystallography. The results reveal that the ligands generally act as ditopic halide receptors with even the largest, L5, being too small to envelop the anion. The ligand’s basicity behaviour parallels that observed for related para-analogues. Despite the ready crystallisation of fluoride, HF2, chloride, bromide, iodide and triiodide salts in the solid state, there appears to be little affinity for halides in aqueous solution in the pH range accessible via potentiometry. The results do give a detailed insight into the role of the aryl ring in restricting the conformational flexibility of the ligands and, hence, the ability to chelate perching anions.

Graphical abstract: Polyaza metacyclophanes as ditopic anion receptors

Supplementary files

Article information

Article type
Paper
Submitted
16 May 2005
Accepted
17 Jun 2005
First published
20 Jul 2005

Org. Biomol. Chem., 2005,3, 2935-2945

Polyaza metacyclophanes as ditopic anion receptors

C. A. Ilioudis and J. W. Steed, Org. Biomol. Chem., 2005, 3, 2935 DOI: 10.1039/B506828B

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