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Li, Lidong
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article
New tetradentate N,N,N,N-chelating α-diimine ligands and their corresponding zinc and nickel complexes
Abstract
<p>A series of zinc complexes of the general formula {[ZnCl(ArNC(An)-C(An)NAr) ]<sup>+</sup>}<sub>2</sub>[Zn<sub>2</sub>Cl<sub>6</sub>]<sup>2-</sup> (where Ar = 2-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl 2a, 2-(1-(1-phenylethyl)-1H-1,2,3- triazol-4-yl)phenyl 2b, 2-(1-phenyl-1H-1,2,3-triazol-4-yl)phenyl 2c; An = acenaphthene backbone) were prepared by the condensation of acenaphthenequinone with the corresponding o-triazolyl-substituted anilines (2-(1-benzyl-1H-1,2,3- triazol-4-yl)aniline 1a, 2-(1-(1-phenylethyl)-1H-1,2,3-triazol-4-yl)aniline 1b, 2-(1-phenyl-1H-1,2,3-triazol-4-yl)aniline 1c) which were formed by the copper(i)-catalyzed Huisgen[3+2] dipolar cycloaddition between 2-ethynylaniline and the corresponding azides in high yields, using anhydrous ZnCl<sub>2</sub> as the metal template, in boiling glacial acetic acid. Zinc complexes of the type [ZnCl(ArNC(An)-C(An)NAr)]<sup>+</sup>[ZnCl<sub>3</sub>(NCCH<sub>3</sub>)] <sup>-</sup> (4a-c) were synthesized by crystallisation of the corresponding complexes 2a-c in acetonitrile, at -20 °C. After removal of zinc dichloride from complexes 2a-c by the addition of potassium oxalate, in dichloromethane, the tetradentate N,N,N,N-chelating α-diimine ligands of the type ArNC(An)-C(An)NAr (5a-c) were obtained. The new ligand precursors and zinc complexes were characterised by elemental analysis, <sup>1</sup>H and <sup>13</sup>C{<sup>1</sup>H} NMR spectroscopy, two-dimensional NMR spectroscopy, and X-ray diffraction. Reaction of the ligand precursors 5a-c with [NiBr<sub>2</sub>(DME)], in dichloromethane, gave nickel complexes of the type [NiBr<sub>2</sub>(ArNC(An)-C(An)NAr)] (6a-c). The results of single crystal X-ray diffraction characterisation and magnetic susceptibility measurements demonstrated that nickel complexes 6a-c possess octahedral geometries around the nickel atoms with variable configurations, the Br atoms of which can be ionized when dissolved in methanol. In preliminary catalytic tests, complexes 6a-c revealed to be active as catalysts for the polymerisation of norbornene and styrene, when activated by cocatalyst MAO. The characterisation of the polymers by <sup>1</sup>H and <sup>13</sup>C{<sup>1</sup>H} NMR spectroscopy, gel permeation chromatography/size-exclusion chromatography (GPC/SEC) revealed that these polymers were formed by a coordination addition mechanism.</p>