2,6-Dibenzhydryl-N-(2-phenyliminoacenaphthylenylidene)-4-methylbenzenamine Nickel Dibromides: Synthesis, Characterization, and Ethylene Polymerization

A series of 2,6-dibenzhydryl-N-(2-phenyliminoacenaphthylenylidene)-4-methylbenzenamines (L1−L5) and the nickel(II) dibromide complexes thereof (C1−C5) were synthesized and fully characterized. The molecular structures of representative complexes were determined by single-crystal X-ray diffraction and revealed a distorted-pyramidal geometry at nickel. All nickel(II) procatalysts exhibited very high activity for the polymerization of ethylene, with activities as high as the range of 107 g of PE (mol of Ni)−1 h−1.

[1]  Wen‐Hua Sun,et al.  Access to highly active and thermally stable iron procatalysts using bulky 2-[1-(2,6-dibenzhydryl-4-methylphenylimino)ethyl]-6-[1-(arylimino)ethyl]pyridine ligands. , 2011, Chemical communications.

[2]  Z. Guan,et al.  Designing late-transition metal catalysts for olefin insertion polymerization and copolymerization. , 2010, Chemical communications.

[3]  D. Stephan,et al.  Synthesis and exchange reactions of Ni-dimine-COD, acetylene and olefin complexes. , 2010, Dalton transactions.

[4]  Z. Guan,et al.  Effect of Ligand Electronics on the Stability and Chain Transfer Rates of Substituted Pd(II) α-Diimine Catalysts(1) , 2010 .

[5]  B. Rieger,et al.  Gas Phase Polymerization of Ethylene with Supported α-Diimine Nickel(II) Catalysts , 2010 .

[6]  Wen‐Hua Sun,et al.  Ferrous and Cobaltous Chlorides Bearing 2,8-Bis(imino)quinolines: Highly Active Catalysts for Ethylene Polymerization at High Temperature , 2010 .

[7]  Yue-sheng Li,et al.  Highly Active Neutral Nickel(II) Catalysts for Ethylene Polymerization Bearing Modified β-Ketoiminato Ligands , 2009 .

[8]  Ying Xu,et al.  Thermostable α-Diimine Nickel(II) Catalyst for Ethylene Polymerization: Effects of the Substituted Backbone Structure on Catalytic Properties and Branching Structure of Polyethylene , 2009 .

[9]  Fosong Wang,et al.  2‐Benzoxazolyl‐6‐[1‐(arylimino)ethyl]pyridyliron(II) Chlorides as Ethylene Oligomerization Catalysts , 2009 .

[10]  Z. Guan,et al.  Nickel(II) and Palladium(II) Polymerization Catalysts Bearing a Fluorinated Cyclophane Ligand: Stabilization of the Reactive Intermediate(1) , 2009 .

[11]  Wen‐Hua Sun,et al.  Synthesis, characterization and ethylene oligomerization of nickel complexes bearing N-(2-(1H-benzo[d]imidazol-2-yl)quinolin-8-yl)benzamide derivatives. , 2009, Dalton transactions.

[12]  Lidong Li,et al.  Synthesis, characterization and ethylene polymerisation of 9,10-phenanthrenequinone-based nickel(II)-α-diimine complexes , 2009 .

[13]  Qing Wu,et al.  Neutral nickel complexes chelating monoamidinate ligands: Syntheses, characterizations and catalytic properties toward ethylene oligomerization and norbornene polymerization , 2009 .

[14]  Wen‐Hua Sun,et al.  2-(1H-2-Benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl Iron(II) and Cobalt(II) Dichlorides: Syntheses, Characterizations, and Catalytic Behaviors toward Ethylene Reactivity , 2009 .

[15]  Wen‐Hua Sun,et al.  2-Oxazoline/benzoxazole-1,10-phenanthrolinylmetal (iron, cobalt or nickel) dichloride : Synthesis, characterization and their catalytic reactivity for the ethylene oligomerization , 2008 .

[16]  G. Bazan,et al.  New polyethylene macroinitiators and their subsequent grafting by atom transfer radical polymerization. , 2008, Journal of the American Chemical Society.

[17]  J. Ziller,et al.  Axial donating ligands: a new strategy for late transition metal olefin polymerization catalysis. , 2008, Journal of the American Chemical Society.

[18]  Xiaochun Zhang,et al.  Reactions of cationic palladium alpha-diimine complexes with nitrogen-containing olefins: Branched polyethylene with carbazole functionalities , 2008 .

[19]  Wen‐Hua Sun,et al.  2-(1-Isopropyl-2-benzimidazolyl)-6-(1-aryliminoethyl)pyridyl transition metal (Fe, Co, and Ni) dichlorides: Syntheses, characterizations and their catalytic behaviors toward ethylene reactivity , 2008 .

[20]  Dae-Won Park,et al.  Ethylene polymerization by sterically and electronically modulated Ni(II) α‐diimine complexes , 2008 .

[21]  Wen‐Hua Sun,et al.  2-(Benzimidazol-2-yl)-1,10-phenanthrolyl metal (Fe and Co) complexes and their catalytic behaviors toward ethylene oligomerization , 2008 .

[22]  Wen‐Hua Sun,et al.  2‐Arylimino‐9‐phenyl‐1,10‐phenanthrolinyl‐iron, ‐cobalt and ‐nickel Complexes: Synthesis, Characterization and Ethylene Oligomerization Behavior , 2007 .

[23]  Wen‐Hua Sun,et al.  Synthesis and characterization of iron and cobalt dichloride bearing 2-quinoxalinyl-6-iminopyridines and their catalytic behavior toward ethylene reactivity , 2007 .

[24]  Wen‐Hua Sun,et al.  Synthesis, Characterization, and Ethylene Oligomerization of Nickel Complexes Bearing N-((Pyridin-2-yl)methylene)quinolin-8-amine Derivatives† , 2007 .

[25]  M. Zhang,et al.  Nickel Complexes Bearing 2‐(Benzimidazol‐2‐yl)‐1,10‐phenanthrolines: Synthesis, Characterization and Their Catalytic Behavior Toward Ethylene Oligomerization , 2007 .

[26]  Wen‐Hua Sun,et al.  Iron(II) and Cobalt(II) 2-(Benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl Complexes as Catalysts for Ethylene Oligomerization and Polymerization , 2007 .

[27]  Wen‐Hua Sun,et al.  Synthesis, Characterization and Ethylene Oligomerization Studies of Nickel Complexes Bearing 2-Benzimidazolylpyridine Derivatives , 2007 .

[28]  Wen‐Hua Sun,et al.  Cobalt and Nickel Complexes Bearing Pyrazolyliminophosphorane Ligands: Synthesis, Characterisation and Catalytic Ethylene Oligomerisation Behaviour , 2006 .

[29]  R. Fröhlich,et al.  Synthesis, characterization and ethylene oligomerization studies of nickel complexes bearing 2-imino-1,10-phenanthrolines , 2006 .

[30]  Li-Ming Tang,et al.  Preparation of linear α‐olefins to high‐molecular weight polyethylenes using cationic α‐diimine nickel(II) complexes containing chloro‐substituted ligands , 2006 .

[31]  Junxian Hou,et al.  Synthesis and Characterization of Tridentate Nickel Complexes Bearing P∧N∧N and P∧N∧P Ligands and Their Catalytic Property in Ethylene Oligomerization , 2006 .

[32]  Qing Wu,et al.  Synthesis of long‐chain‐branched polyethylene by ethylene homopolymerization with a novel nickel(II) α‐diimine catalyst , 2005 .

[33]  Wei Chen,et al.  Nickel (II) complexes bearing 2-ethylcarboxylate-6-iminopyridyl ligands: synthesis, structures and their catalytic behavior for ethylene oligomerization and polymerization , 2005 .

[34]  Huarong Liu,et al.  Highly active new α-diimine nickel catalyst for the polymerization of α-olefins , 2005 .

[35]  L. Cavallo,et al.  (E)-(Z) selectivity in the polymerization of 2-butene promoted by Ni(II) brookhart-type catalysts , 2005 .

[36]  L. Saussine,et al.  New Nickel Ethylene Oligomerization Catalysts Bearing Bidentate P,N-Phosphinopyridine Ligands with Different Substituents α to Phosphorus† , 2004 .

[37]  J. Ziller,et al.  Cyclophane-based highly active late-transition-metal catalysts for ethylene polymerization. , 2004, Angewandte Chemie.

[38]  H. Alt,et al.  (α-Diimine)nickel(II) complexes containing chloro substituted ligands as catalyst precursors for the oligomerization and polymerization of ethylene , 2003 .

[39]  M. Brookhart,et al.  Mechanistic studies of nickel(II) alkyl agostic cations and alkyl ethylene complexes: investigations of chain propagation and isomerization in (alpha-diimine)Ni(II)-catalyzed ethylene polymerization. , 2003, Journal of the American Chemical Society.

[40]  V. C. Gibson,et al.  Advances in non-metallocene olefin polymerization catalysis. , 2003, Chemical reviews.

[41]  G. Suranna,et al.  Synthesis, characterisation and catalytic activity of Pd(II) and Ni(II) complexes with new cyclic α-diphenylphosphino-ketoimines. Crystal structure of 2,6-diisopropyl-N-(2-diphenylphosphino-cyclopentylidene)aniline and of 2,6-diisopropyl-N-(2-diphenylphosphino-cyclohexylidene)aniline , 2002 .

[42]  Biao Wu,et al.  Synthesis and characterization of novel nickel(II) complexes bearing N,P ligands and their catalytic activity in ethylene oligomerization , 2002 .

[43]  You-liang Hu,et al.  Ethylene oligomerization promoted by group 8 metal complexes containing 2-(2-pyridyl)quinoxaline ligands , 2002 .

[44]  J. Wood,et al.  The formation and polymerization behavior of Ni(II) α-diimine complexes using various aluminum activators , 2002 .

[45]  S. Mecking.  Cationic nickel and palladium complexes with bidentate ligands for the CC linkage of olefins , 2000 .

[46]  M. Brookhart,et al.  Late-metal catalysts for ethylene homo- and copolymerization. , 2000, Chemical reviews.

[47]  E. Oñate,et al.  Synthesis of branched polyethylene using (α-diimine)nickel(II) catalysts : influence of temperature, ethylene pressure, and ligand structure on polymer properties , 2000 .

[48]  L. Cavallo,et al.  Mechanism ofUnlikeStereoselectivity in 1-Alkene Primary Insertions: Syndiospecific Propene Polymerization by Brookhart-Type Nickel(II) Catalysts , 2000 .

[49]  R. F. Souza,et al.  13C NMR Determination of the Composition of Linear Low-Density Polyethylene Obtained with [η3-Methallyl-nickel-diimine]PF6 Complex , 1999 .

[50]  M. Brookhart,et al.  Ethylene Oligomerization and Propylene Dimerization Using Cationic (α-Diimine)nickel(II) Catalysts , 1999 .

[51]  R. Grubbs,et al.  Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization , 1998 .

[52]  Maurice Brookhart,et al.  Highly Active Iron and Cobalt Catalysts for the Polymerization of Ethylene , 1998 .

[53]  Andrew L. Johnson,et al.  Preparation of Linear α-Olefins Using Cationic Nickel(II) α-Diimine Catalysts , 1997 .

[54]  T. Ziegler,et al.  A Density Functional Study of Nickel(II) Diimide Catalyzed Polymerization of Ethylene , 1997 .

[55]  D. J. Tempel,et al.  Living Polymerization of α-Olefins Using NiII−α-Diimine Catalysts. Synthesis of New Block Polymers Based on α-Olefins , 1996 .

[56]  Maurice Brookhart,et al.  New Pd(II)- and Ni(II)-Based Catalysts for Polymerization of Ethylene and .alpha.-Olefins , 1995 .