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Issue 1, 2014
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Click synthesis of symmetric bis-triazol ligands and full characterisation of their copper(II)-complexes

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Abstract

Eight novel ligands were prepared from a known symmetric diaza-18-crown-6 (cyclic ligand) and two commercial N,N′-dimethyl-alkyl diamines (acyclic ligands) via the Cu(I)-catalyzed Huisgen dipolar cycloaddition. All C2-symmetric isolated ligands readily formed stable crystalline 1 : 1-copper(II) complexes with cupric perchlorate. Their structural, electrochemical and physico-chemical properties were fully investigated with the help of X-ray diffraction, cyclic voltammetry, FT-IR, UV-visible, and electron paramagnetic resonance (EPR) spectroscopies. Planar – or nearly planar – arrangement of the two N3-triazole nitrogens and the two tertiary amine pivot nitrogens was found in one single four-coordinated species, in four five-coordinated species, and three six-coordinated species, with one or two solvent molecule(s), or two oxygen atoms of the crown ether, occupying the axial position(s) in the solid sate. The electron-donating or electron-withdrawing effect of the N1-substituent on the triazol was found to influence the Cu(II)/Cu(I) redox potential of all studied complexes in DMF. The EPR-spectrum of cyclic complexes in frozen DMF at 100 K exhibited two mononuclear species, one of them likely promoting the formation of dinuclear species as a minor component, whereas most acyclic complex spectra were quite similar.

Graphical abstract: Click synthesis of symmetric bis-triazol ligands and full characterisation of their copper(ii)-complexes

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Publication details

The article was received on 28 May 2013, accepted on 31 Oct 2013 and first published on 01 Nov 2013


Article type: Paper
DOI: 10.1039/C3NJ00570D
Citation: New J. Chem., 2014,38, 419-429
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    Click synthesis of symmetric bis-triazol ligands and full characterisation of their copper(II)-complexes

    Z. Benkhellat, M. Allali, M. Beley, E. Wenger, M. Bernard, N. Parizel, K. Selmeczi and J. Joly, New J. Chem., 2014, 38, 419
    DOI: 10.1039/C3NJ00570D

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