Issue 17, 2009

Formation of a narrow chiral cavity in bis-copper(ii) complexes of ferrocenylmethyl-l-tyrosine and its interaction with achiral guests

Abstract

Earlier we reported the tendency of ferrocenylmethyl substituted amino acids to organize around Cu(II) in a C2 symmetry. In this paper we have utilized this property to form a chiral cavity using a L-tyrosine derivative. Structural characterization of [CuII(S-fTyr)2(MeCN)2] (1), where S-fTyr1 is ferrocenylmethyl-L-tyrosinate, showed that the alignment of two tyrosine aromatic rings around the fifth coordination site generates a narrow cavity. Structural characterization of [Cu(S-fTyr)2(pyrazine)] (2), [Cu(S-fTyr)2(pyridine)] (3), [Cu(S-fTyr)2(bpy)] (4) and [Cu(S-fTyr)2(H2O)] (5) revealed that planar heterocyclic N-donors as guests stabilized the cavity, while polar water molecules destroyed it. Electrochemical properties of the complexes showed a shift of CuII/CuI potentials depending on the strength of the guest binding inside the cavity.

Graphical abstract: Formation of a narrow chiral cavity in bis-copper(ii) complexes of ferrocenylmethyl-l-tyrosine and its interaction with achiral guests

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2008
Accepted
04 Mar 2009
First published
27 Mar 2009

Dalton Trans., 2009, 3230-3236

Formation of a narrow chiral cavity in bis-copper(II) complexes of ferrocenylmethyl-L-tyrosine and its interaction with achiral guests

S. C. Sahoo and M. Ray, Dalton Trans., 2009, 3230 DOI: 10.1039/B819915A

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