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Issue 17, 2009
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Formation of a narrow chiral cavity in bis-copper(ii) complexes of ferrocenylmethyl-l-tyrosine and its interaction with achiral guests

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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

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Article information


Submitted
10 Nov 2008
Accepted
04 Mar 2009
First published
27 Mar 2009

Dalton Trans., 2009, 3230-3236
Article type
Paper

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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