Issue 8, 2011

Ferrocene-amino acidmacrocycles as hydrazone-based receptors for anions

Abstract

We report the synthesis of a family of new macrocyclic hydrazone-based anion receptors. Formed from the reaction between isophthalaldehyde and a helical amino acid-disubstituted ferrocene dihydrazide, these macrocycles contain from one to eight ferrocene moieties. The isolation of the four smallest of the macrocycles and their characterisation by UV-Vis, CD and NMR spectroscopy is described. The conformation of the macrocycles is explored, particularly with reference to the formation of a helical intramolecularly hydrogen-bonded structure. An investigation of the use of these macrocycles as anion-receptors shows that they are all effective hosts; the larger macrocycles show the highest affinities for anions. Studies using NMR spectroscopy suggest that the anion-recognition results primarily from the formation of multiple hydrogen bonds between the anions and the electropositive N–H protons of the acylhydrazones.

Graphical abstract: Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Mar 2011
Accepted
28 Apr 2011
First published
19 May 2011

Chem. Sci., 2011,2, 1560-1567

Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions

S. R. Beeren and J. K. M. Sanders, Chem. Sci., 2011, 2, 1560 DOI: 10.1039/C1SC00168J

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