Nickel(II) Complexes with Three-Dimensional Geometry α-Diimine Ligands: Synthesis and Catalytic Activity toward Copolymerization of Norbornene

A series of three-dimensional geometry 9,10-dihydro-9,10-ethanoanthracene-11,12-diimines (L1–L4) and their nickel(II) dibromide complexes (C1–C4) were synthesized and characterized. The nickel complexes C1–C4, with three-dimensional geometry, exhibited very high activities for norbornene (NB) homopolymerization with only B(C6F5)3 as cocatalyst,: for C2 even up to 5.53 × 107 g of polymer/((mol of Ni) h). To investigate the activation of polar monomer, complexes C2 and C3 were selected for copolymerization of NB and 5-norbornene-2-yl acetate (NB-OCOMe) in relatively high activities (1.6–5.8 × 105g of polymer/((mol of Ni) h)) and high molecular weights ((0.2–2.8) × 105 g/mol) as well as narrow molecular weight distributions (MWD < 2 for all polymers) depending on the variation of feed ratios. The reactivity ratios of the NB and NB-OCOMe monomers for C2/B(C6F5)3 system by the Kelen–Tudos method were determined to be rNB-OCOMe = 0.05 and rNB = 6.72, respectively. Moreover, the mechanism of polymerization catal...

[1]  Yiwang Chen,et al.  Ni(II) and Pd(II) complexes bearing benzocyclohexane–ketoarylimine for copolymerization of norbornene with 5‐norbornene‐2‐carboxylic ester , 2012 .

[2]  A. R. Galletti,et al.  Highly active and easily accessible catalysts for vinyl polymerization of norbornene obtained by oxidative addition of salicylaldimine ligands to bis(1,5‐cyclooctadiene)nickel(0) and methylaluminoxane , 2012 .

[3]  I. Hierro,et al.  Synthesis of titanium alkoxide complexes with alkyl lactate ligands. Asymmetric epoxidation of cinnamyl alcohol , 2012 .

[4]  L. Chen,et al.  Mono- and di-nuclear nickel(II) complexes bearing 3-aryliminomethyl-2-hydroxybenzaldehydes: Synthesis, structures and vinyl polymerization of norbornene , 2012 .

[5]  T. Marks,et al.  Ligand steric and fluoroalkyl substituent effects on enchainment cooperativity and stability in bimetallic nickel(II) polymerization catalysts. , 2012, Chemistry.

[6]  Qing Wu,et al.  Substituent Effects of the Backbone in α-Diimine Palladium Catalysts on Homo- and Copolymerization of Ethylene with Methyl Acrylate , 2012 .

[7]  Wen‐Hua Sun,et al.  Nickel halide complexes bearing 2-benzimidazolyl-N-arylquinoline-8-carboxamide derived ligands: Synthesis, characterization and catalytic behavior towards ethylene oligomerization and the vinyl polymerization of norbornene , 2012 .

[8]  Lei Zhang,et al.  Ni(II) and Fe(II) complexes based on bis(imino)aryl pincer ligands: synthesis, structural characterization and catalytic activities. , 2012, Dalton transactions.

[9]  G. Jin,et al.  Synthesis and Characterization of Nickel(II) and Palladium(II) Complexes based on Tridentate [N–NP] and [N–NS] Ligands and Their Applications in Norbornene Polymerization , 2012 .

[10]  T. Marks,et al.  Suppression of β-Hydride Chain Transfer in Nickel(II)-Catalyzed Ethylene Polymerization via Weak Fluorocarbon Ligand–Product Interactions , 2012 .

[11]  Jean-Christophe Daigle,et al.  Structure-activity relationship of palladium phosphanesulfonates: toward highly active palladium-based polymerization catalysts. , 2012, Chemistry.

[12]  Wen‐Hua Sun,et al.  Vinyl Polymerization of Norbornene on Nickel Complexes with Bis(imino)pyridine Ligands Containing Electron-Withdrawing Groups , 2012 .

[13]  Yue-sheng Li,et al.  Ligand Steric and Electronic Effects on β-Ketiminato Neutral Nickel(II) Olefin Polymerization Catalysts , 2012 .

[14]  K. Vijayakrishna,et al.  Highly active novel Ni-diimine pre-catalyst containing bis-ketimine ligand for the vinyl polymerization of norbornene , 2012, Polymer Bulletin.

[15]  Yiwang Chen,et al.  Copolymerization of norbornene with methoxycarbonylnorbornene catalyzed by Ni{CF3C(O)CHC[N(naphthyl)]CH3}2/B(C6F5)3 catalytic system and good processability for Dry/Wet phase inversion and electrospinning technique , 2011 .

[16]  Yiwang Chen,et al.  Ni(II) and Pd(II) complexes bearing novel bis(β‐ketoamino) ligand and their catalytic activity toward copolymerization of norbornene and 5‐norbornene‐2‐yl acetate combined with B(C6F5)3 , 2011 .

[17]  A. Ravasio,et al.  Copolymerization of Ethylene with Norbornene by Neutral Aryl Phosphine Sulfonate Palladium Catalyst , 2011 .

[18]  Z. Guan,et al.  Systematic Investigation of Ligand Substitution Effects in Cyclophane-Based Nickel(II) and Palladium(II) Olefin Polymerization Catalysts(1) , 2011 .

[19]  Wen‐Hua Sun,et al.  2,6-Dibenzhydryl-N-(2-phenyliminoacenaphthylenylidene)-4-methylbenzenamine Nickel Dibromides: Synthesis, Characterization, and Ethylene Polymerization , 2011 .

[20]  T. Marks,et al.  Ethylene polymerization characteristics of an electron-deficient nickel(II) phenoxyiminato catalyst modulated by non-innocent intramolecular hydrogen bonding , 2010 .

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

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

[23]  B. S. Lima-Neto,et al.  The influence of perhydroazepine and piperidine as further ancillary ligands on Ru-PPh3-based catalysts for ROMP of norbornene and norbornadiene , 2010 .

[24]  W. Scherer,et al.  On the electronic structure of Ni(II) complexes that feature chelating bisguanidine ligands. , 2010, Chemistry.

[25]  Ke-Xin Zhang,et al.  Synthesis of Hetero-Grafted Amphiphilic Diblock Molecular Brushes and Their Self Assembly in Aqueous Medium , 2010 .

[26]  Yue-sheng Li,et al.  High-Temperature Living Copolymerization of Ethylene with Norbornene by Titanium Complexes Bearing Bidentate [O, P] Ligands , 2009 .

[27]  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 .

[28]  Yiwang Chen,et al.  Copolymerization of norbornene and 5‐norbornene‐2‐yl acetate using novel bis(β‐ketonaphthylamino)Ni(II)/B(C6F5)3/AlEt3 catalytic system , 2009 .

[29]  B. S. Lima-Neto,et al.  Ability of Ru complexes for ROMP tuned through a combination of phosphines and amines , 2009 .

[30]  Brandon A. Rodriguez,et al.  Bimetallic effects for enhanced polar comonomer enchainment selectivity in catalytic ethylene polymerization. , 2009, Journal of the American Chemical Society.

[31]  R. T. Mathers,et al.  Functional Hyperbranched Polymers Using Ring-Opening Metathesis Polymerization of Dicyclopentadiene with Monoterpenes , 2009 .

[32]  M. Yamashita,et al.  Polymerization of norbornene with a pendent sulfonyl fluoride group catalyzed by palladium complex bearing tBu3P ligand , 2008 .

[33]  C. Ha,et al.  Influence of type and positioning of N-aryl substituents on vinyl polymerization of norbornene by Ni(II) α-diimine complexes , 2008 .

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

[35]  Brandon A. Rodriguez,et al.  Neutral bimetallic nickel(II) phenoxyiminato catalysts for highly branched polyethylenes and ethylene-norbornene copolymerizations , 2008 .

[36]  M. Weck,et al.  Noncovalently functionalized poly(norbornene)s possessing both hydrogen bonding and coulombic interactions , 2007 .

[37]  S. Ihm,et al.  Polymerization of norbornene using novel palladium carboxylate/boron trifluoride etherate catalyst system , 2006 .

[38]  Yuan‐Biao Huang,et al.  Syntheses of iron, cobalt, chromium, copper and zinc complexes with bulky bis(imino)pyridyl ligands and their catalytic behaviors in ethylene polymerization and vinyl polymerization of norbornene , 2006 .

[39]  A. Bousquet,et al.  Hybrid Polymer Particles by Tandem Ring-Opening Metathesis and Atom Transfer Radical Polymerizations in Aqueous Miniemulsion , 2006 .

[40]  Bipin K. Shah,et al.  Photogeneration of heptacene in a polymer matrix. , 2006, Journal of the American Chemical Society.

[41]  J. F. Stoddart,et al.  Noncovalent Side-Chain Functionalization of Terpolymers , 2006 .

[42]  Seunghwan Lee,et al.  Effects of tris(pentafluorophenyl)borane on the activation of zerovalent-nickel complex in the addition polymerization of norbornene , 2005 .

[43]  Yue-sheng Li,et al.  Synthesis, structure and norbornene polymerization behavior of neutral palladium complexes , 2004 .

[44]  L. Weng,et al.  Synthesis, Molecular Structures, and Norbornene Addition Polymerization Activity of the Neutral Nickel Catalysts Supported by β-Diketiminato [N, N], Ketiminato [N, O], and Schiff-Base [N, O] Ligands⊥ , 2004 .

[45]  Ayusman Sen,et al.  Addition Polymerization of Functionalized Norbornenes: The Effect of Size, Stereochemistry, and Coordinating Ability of the Substituent , 2004 .

[46]  S. Ihm,et al.  Novel bis(acetylacetonate)palladium/boron trifluoride etherate catalyst system for the polymerization of norbornene , 2003 .

[47]  Xiaoyan He,et al.  Nickel(II) Complexes Bearing N,O-Chelate Ligands: Synthesis, Solid-Structure Characterization, and Reactivity toward the Polymerization of Polar Monomer , 2003 .

[48]  Robert A. Shick,et al.  Addition Polymerization of Norbornene-Type Monomers Using Neutral Nickel Complexes Containing Fluorinated Aryl Ligands , 2003 .

[49]  C. Janiak,et al.  Borane activators for late-transition metal catalysts in norbornene polymerization , 2002 .

[50]  T. Marks,et al.  Cocatalysts for metal-catalyzed olefin polymerization: activators, activation processes, and structure-activity relationships. , 2000, Chemical reviews.

[51]  D. Wass,et al.  Mechanistic Studies of Alkene/CO Polymerization with Palladium Complexes Promoted by B(C6F5)3 , 2000 .

[52]  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 .

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

[54]  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 .

[55]  R. Grubbs,et al.  Synthesis of ABA triblock copolymers of norbornenes and 7-oxanorbornenes via living ring-opening metathesis polymerization using well-defined, bimetallic ruthenium catalysts , 1996 .

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

[57]  G. Koten,et al.  Alkene and carbon monoxide insertion reactions of nitrogen-coordinated monoorganopalladium(II) complexes: The stepwise construction of alternating copolymers of CO and alkenes on a palladium center , 1995 .

[58]  Ayusman Sen.  Mechanistic aspects of metal-catalyzed alternating copolymerization of olefins with carbon monoxide , 1993 .

[59]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[60]  Archana Sharma,et al.  Sequential oscillations in bromine hydrolysis controlled oscillators in a closed reactor , 1993 .

[61]  Hans W. Horn,et al.  Fully optimized contracted Gaussian basis sets for atoms Li to Kr , 1992 .

[62]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[63]  T. Kelen.  Analysis of the Linear Methods for Determining Copolymerization Reactivity Ratios. I. A New Improved Linear Graphic Method , 1975 .

[64]  D. Breslow,et al.  BIS-(CYCLOPENTADIENYL)-TITANIUM DICHLORIDE —ALKYLALUMINUM COMPLEXLS AS CATALYSTS FOR THE POLYMERIZATION OF ETHYLENE , 1957 .

[65]  Hans-Dieter Martin,et al.  Das Mülheimer Normaldruck‐Polyäthylen‐Verfahren , 1955 .