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

Zakia Benkhellat 1 Mustapha Allali 1 Marc Beley 1 Emmanuel Wenger 2 Maxime Bernard 3 Nathalie Parizel 3 Katalin Selmeczi 1 Jean-Pierre Joy 1
3 TGE Réseau National de RPE interdisciplinaire - 3443 - RENARD
LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, FR-CNRS 3443, UPD5 - Université Paris Descartes - Paris 5 : FR 3443, CNRS - Centre National de la Recherche Scientifique : FR 3443, ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL, AMU - Aix Marseille Université, SU - Sorbonne Université, Université de Lille, UNISTRA - Université de Strasbourg
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 C-2-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.
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Zakia Benkhellat, Mustapha Allali, Marc Beley, Emmanuel Wenger, Maxime Bernard, et al.. Click synthesis of symmetric bis-triazol ligands and full characterisation of their copper(II)-complexes. New Journal of Chemistry, Royal Society of Chemistry, 2014, 38 (1), pp.419-429. ⟨10.1039/c3nj00570d⟩. ⟨hal-01494407⟩

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