Issue 24, 2008
From the journal:

Dalton Transactions

Synthesis, characterization and dioxygen reactivity of copper(i) complexes with glycoligands†‡

Ziad Damaj,a   Federico Cisnetti,c   Laurent Dupont,a   Eric Henon,d   Clotilde Policar*c  and  Emmanuel Guillon*ab  

* Corresponding authors

a Institut de Chimie Moléculaire de Reims, Equipe Chimie de Coordination, Université de Reims Champagne-Ardenne, UMR CNRS 6229, Faculté des Sciences, B.P. 1039, Reims cedex 2, France
E-mail: emmanuel.guillon@univ-reims.fr
Fax: +33 (0)3 26 91 32 43

b ESIEC (Ecole Supérieure d'Ingénieurs en Emballage et Conditionnement), Pôle Technologique Henri Farman, B.P. 1029, Reims cedex 2, France

c Institut de Chimie Moléculaire et des Matériaux d'Orsay, Equipe de Chimie Bio-organique et Bio-inorganique, Université Paris-Sud 11, UMR CNRS 8182, Orsay cedex, France
E-mail: cpolicar@icmo.u-psud.fr
Fax: +33 (0)1 69 15 72 81

d Institut de Chimie Moléculaire de Reims, Equipe BSMA, Université de Reims Champagne-Ardenne, UMR CNRS 6229, Faculté des Sciences, B.P. 1039, Reims cedex 2, France
E-mail: eric.henon@univ-riems.fr
Fax: +33 (0)3 26 91 84 97

Abstract

A new family of copper(I) complexes with “glycoligands” containing a central saccharide scaffold, with 2-picolyl ether groups or 2-picolylamine or N-imidazolylamine groups, has been prepared and characterized. For this purpose, the following tetradentate ligands have been synthesized: methyl 2,3-di-O-(2-picolyl)-α-D-lyxofuranoside (L1), 1,5-anhydro-2-deoxy-3,4-di-O-(2-picolyl)-D-galactitol (L2), 5-(amino-N-(2-salicyl))-5-deoxy-1,2-O-isopropylidene-3-O-(2-picolyl)-α-D-xylofuranose (L3), and 5-(amino-N-(2-salicyl))-5-deoxy-1,2-O-isopropylidene-3-O-(methylimidazol-2-yl)-α-D-xylofuranose (L4). The ligands and the complexes were characterized by elemental analysis, IR, 1H and 13C NMR spectroscopies, ESI mass spectrometry, and cyclic voltammetry. Collaterally with the experimental work, HF-DFT(B3LYP/6–31G*) computations were performed to obtain additional structural information. The Cu(I) complexes are found to be pentacoordinated. The redox properties and the O2-reactivity of the CuILn complexes have been studied. Reactions of Cu(I) complexes with dioxygen in ethanol yield stable Cu(II) complexes as confirmed by UV-visible spectrophotometry and EPR spectroscopy.

Graphical abstract: Synthesis, characterization and dioxygen reactivity of copper(i) complexes with glycoligands

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Article information

DOI
https://doi.org/10.1039/B801109E
Article type
Paper
Submitted
21 Jan 2008
Accepted
28 Mar 2008
First published
07 May 2008

Dalton Trans., 2008, 3235-3245

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Synthesis, characterization and dioxygen reactivity of copper(I) complexes with glycoligands

Z. Damaj, F. Cisnetti, L. Dupont, E. Henon, C. Policar and E. Guillon, Dalton Trans., 2008, 3235 DOI: 10.1039/B801109E

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