Ethylene (Co)polymerization by Binuclear Nickel Phenoxyiminato Catalysts with Cofacial Orientation

Macromolecules

Volumn 49, Issue 23, 2016, Pages 8848-8854

  Chen, Zhongtao ^a   Yao, Erdong ^a   Wang, Jianchun ^a   Gong, Xinyi ^a   Ma, Yuguo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BINS; CATALYST ACTIVITY; CATALYSTS; COPOLYMERIZATION; ETHYLENE; MUSCULOSKELETAL SYSTEM; POLYMERIZATION;

BIMETALLIC EFFECTS; COORDINATION PLANE; ETHYLENE POLYMERIZATION; NICKEL COMPLEX; POLAR MONOMER; STERIC HINDRANCES; TERT-BUTYL GROUP;

NICKEL;

EID: 85006278255     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.6b02078     Document Type: Article

References (41)

1. Johnson, L. K.; Killian, C. M.; Brookhart, M. New Pd(II)- and Ni(II)-Based Catalysts for Polymerization of Ethylene and α-Olefins J. Am. Chem. Soc. 1995, 117, 6414 10.1021/ja00128a054
2. Johnson, L. K.; Mecking, S.; Brookhart, M. Copolymerization of Ethylene and Propylene with Functionalized Vinyl Monomers by Palladium(II) Catalysts J. Am. Chem. Soc. 1996, 118, 267 10.1021/ja953247i
3. Wang, C.; Friedrich, S.; Younkin, T. R.; Li, R. T.; Grubbs, R. H.; Bansleben, D. A.; Day, M. W. Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization Organometallics 1998, 17, 3149 10.1021/om980176y
4. Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Neutral, Single-Component Nickel (II) Polyolefin Catalysts That Tolerate Heteroatoms Science 2000, 287, 460 10.1126/science.287.5452.460
5. Connor, E. F.; Younkin, T. R.; Henderson, J. I.; Waltman, A. W.; Grubbs, R. H. Synthesis of Neutral Nickel Catalysts for Ethylene Polymerization-the Influence of Ligand Size on Catalyst Stability Chem. Commun. 2003, 2272 10.1039/b306701g
6. Waltman, A. W.; Younkin, T. R.; Grubbs, R. H. Insights into the Deactivation of Neutral Nickel Ethylene Polymerization Catalysts in the Presence of Functionalized Olefins Organometallics 2004, 23, 5121 10.1021/om049360b
7. Zuideveld, M. A.; Wehrmann, P.; Rohr, C.; Mecking, S. Remote Substituents Controlling Catalytic Polymerization by Very Active and Robust Neutral Nickel(II) Complexes Angew. Chem., Int. Ed. 2004, 43, 869 10.1002/anie.200352062
8. Mu, H. L.; Ye, W. P.; Song, D. P.; Li, Y. S. Highly Active Single-Component Neutral Nickel Ethylene Polymerization Catalysts: The Influence of Electronic Effects and Spectator Ligands Organometallics 2010, 29, 6282 10.1021/om100658j
9. Rhinehart, J. L.; Brown, L. A.; Long, B. K. A Robust Ni(II) α-Diimine Catalyst for High Temperature Ethylene Polymerization J. Am. Chem. Soc. 2013, 135, 16316 10.1021/ja408905t
10. Dai, S.; Sui, X.; Chen, C. Highly Robust Palladium(II) α-Diimine Catalysts for Slow-Chain-Walking Polymerization of Ethylene and Copolymerization with Methyl Acrylate Angew. Chem., Int. Ed. 2015, 54, 9948 10.1002/anie.201503708
11. Chen, Z.; Mesgar, M.; White, P. S.; Daugulis, O.; Brookhart, M. Synthesis of Branched Ultrahigh-Molecular-Weight Polyethylene Using Highly Active Neutral, Single-Component Ni(II) Catalysts ACS Catal. 2015, 5, 631 10.1021/cs501948d
12. Weberski, M. P., Jr.; Chen, C.; Delferro, M.; Zuccaccia, C.; Macchioni, A.; Marks, T. J. Suppression of β-Hydride Chain Transfer in Nickel(II)-Catalyzed Ethylene Polymerization via Weak Fluorocarbon Ligand-Product Interactions Organometallics 2012, 31, 3773 10.1021/om3002735
13. Wang, J.; Yao, E.; Chen, Z.; Ma, Y. Fluorinated Nickel(II) Phenoxyiminato Catalysts: Exploring the Role of Fluorine Atoms in Controlling Polyethylene Productivities and Microstructures Macromolecules 2015, 48, 5504 10.1021/acs.macromol.5b01090
14. Cai, Z.; Xiao, D.; Do, L. H. Fine-Tuning Nickel Phenoxyimine Olefin Polymerization Catalysts: Performance Boosting by Alkali Cations J. Am. Chem. Soc. 2015, 137, 15501 10.1021/jacs.5b10351
15. Delferrro, M.; Marks, T. J. Multinuclear Olefin Polymerization Catalysts Chem. Rev. 2011, 111, 2450 10.1021/cr1003634
16. Makio, H.; Terao, H.; Iwashita, A.; Fujita, T. FI Catalysts for Olefin Polymerization-A Comprehensive Treatment Chem. Rev. 2011, 111, 2363 10.1021/cr100294r
17. Rodriguez, B. A.; Delferro, M.; Marks, T. J. Neutral Bimetallic Nickel(II) Phenoxyiminato Catalysts for Highly Branched Polyethylenes and Ethylene-Norbornene Copolymerizations Organometallics 2008, 27, 2166 10.1021/om800208f
18. McInnis, J. P.; Delferro, M.; Marks, T. J. Multinuclear Group 4 Catalysis: Olefin Polymerization Pathways Modified by Strong Metal-Metal Cooperative Effects Acc. Chem. Res. 2014, 47, 2545 10.1021/ar5001633
19. Sujith, S.; Joe, D. J.; Na, S. J.; Park, Y. W.; Chow, C. H.; Lee, B. Y. Ethylene/Polar Norbornene Copolymerizations by Bimetallic Salicylaldimine-Nickel Catalysts Macromolecules 2005, 38, 10027 10.1021/ma051344i
20. Hu, T.; Li, Y. G.; Li, Y. S.; Hu, N. H. Novel Highly Active Binuclear Neutral Nickel and Palladium Complexes as Precatalysts for Norbornene Polymerization J. Mol. Catal. A: Chem. 2006, 253, 155 10.1016/j.molcata.2006.03.008
21. Na, S. J.; Joe, D. J.; Sujith, S.; Han, W. S.; Kang, S. O.; Lee, B. Y. Bimetallic Nickel Complexes of Macrocyclic Tetraiminodiphenols and Their Ethylene Polymerization J. Organomet. Chem. 2006, 691, 611 10.1016/j.jorganchem.2005.09.032
22. Wang, W. H.; Jin, G. X. Binuclear Neutral Nickel Complexes Bearing Bis(bidentate) Salicylaldiminato Ligands: Synthesis, Structure and Ethylene Polymerization Behavior Inorg. Chem. Commun. 2006, 9, 548 10.1016/j.inoche.2006.02.015
23. Zhang, D.; Jin, G.-X. Bimetallic Nickel Complexes of Trimethyl Phenyl Linked Salicylaldimine Ligands: Synthesis, Structure and Their Ethylene Polymerization Behaviors Inorg. Chem. Commun. 2006, 9, 1322 10.1016/j.inoche.2006.08.017
24. Chen, Q.; Yu, J.; Huang, J. Arene-Bridged Salicylaldimine-Based Binuclear Neutral Nickel(II) Complexes: Synthesis and Ethylene Polymerization Activities Organometallics 2007, 26, 617 10.1021/om060778e
25. Radlauer, M. R.; Day, M. W.; Agapie, T. Bimetallic Effects on Ethylene Polymerization in the Presence of Amines: Inhibition of the Deactivation by Lewis Bases J. Am. Chem. Soc. 2012, 134, 1478 10.1021/ja210990t
26. Radlauer, M. R.; Day, M. W.; Agapie, T. Dinickel Bisphenoxyiminato Complexes for the Polymerization of Ethylene and α-Olefins Organometallics 2012, 31, 2231 10.1021/om2011694
27. Radlauer, M. R.; Buckley, A. K.; Henling, L. M.; Agapie, T. Bimetallic Coordination Insertion Polymerization of Unprotected Polar Monomers: Copolymerization of Amino Olefins and Ethylene by Dinickel Bisphenoxyiminato Catalysts J. Am. Chem. Soc. 2013, 135, 3784 10.1021/ja4004816
28. Takeuchi, D.; Chiba, Y.; Takano, S.; Osakada, K. Double-Decker-Type Dinuclear Nickel Catalyst for Olefin Polymerization: Efficient Incorporation of Functional Co-monomers Angew. Chem., Int. Ed. 2013, 52, 12536 10.1002/anie.201307741
29. He, S.; Wang, F.; Tong, W. L.; Yiu, S. M.; Chan, M. C. W. Topologically Diverse Shape-Persistent Bis-(Zn-Salphen) Catalysts: Efficient Cyclic Carbonate Formation under Mild Conditions Chem. Commun. 2016, 52, 1017 10.1039/C5CC08794E
30. Tong, W. L.; Yiu, S. M.; Chan, M. C. W. Crowded Bis-(M-salphen) [M = Pt(II), Zn(II)] Coordination Architectures: Luminescent Properties and Ion-Selective Responses Inorg. Chem. 2013, 52, 7114 10.1021/ic400692x
31. Delferro, M.; McInnis, J. P.; Marks, T. J. Ethylene Polymerization Characteristics of an Electron-Deficient Nickel(II) Phenoxyiminato Catalyst Modulated by Non-Innocent Intramolecular Hydrogen Bonding Organometallics 2008, 27, 2166 10.1021/om800208f
32. Hidai, M.; Kashiwagi, T.; Ikeuchi, T.; Uchida, Y. Oxidative Additions to Nickel(0): Preparation and Properties of a New Series of Arylnickel(II) Complexes J. Organomet. Chem. 1971, 30, 279 10.1016/S0022-328X(00)90208-0
33. Connor, E. F.; Younkin, T. R.; Henderson, J. I.; Hwang, S. J.; Grubbs, R. H.; Roberts, W. P.; Litzau, J. J. Linear Functionalized Polyethylene Prepared with Highly Active Neutral Ni(II) Complexes J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2842 10.1002/pola.10370
34. II Complexes ChemCatChem 2016, 8, 434 10.1002/cctc.201501041
35. Salata, M. R.; Marks, T. J. Catalyst Nuclearity Effects in Olefin Polymerization. Enhanced Activity and Comonomer Enchainment in Ethylene + Olefin Copolymerizations Mediated by Bimetallic Group 4 Phenoxyiminato Catalysts Macromolecules 2009, 42, 1920 10.1021/ma8020745
36. Han, S.; Yao, E.; Qin, W.; Zhang, S.; Ma, Y. Binuclear Heteroligated Titanium Catalyst Based on Phenoxyimine Ligands: Synthesis, Characterization, and Ethylene (Co)polymerization Macromolecules 2012, 45, 4054 10.1021/ma300384w
37. Takano, S.; Takeuchi, D.; Osakada, K. Olefin Polymerization Catalyzed by Double-Decker Dipalladium Complexes: Low Branched Poly(a-Olefin)s by Selective Insertion of the Monomer Molecule Chem.-Eur. J. 2015, 21, 16209 10.1002/chem.201501991
38. 13C NMR Analysis of R-Olefin Enchainment in Poly(R-olefins) Produced with Nickel and Palladium R-Diimine Catalysts Macromolecules 2007, 40, 410 10.1021/ma061547m
39. Liu, J.; Chen, D.; Wu, H.; Xiao, Z.; Gao, H.; Zhu, F.; Wu, Q. Polymerization of α-Olefins Using a Camphyl α-Diimine Nickel Catalyst at Elevated Temperature Macromolecules 2014, 47, 3325 10.1021/ma5004634
40. Williams, B. S.; Leatherman, M. D.; White, P. S.; Brookhart, M. Reactions of Vinyl Acetate and Vinyl Trifluoroacetate with Cationic Diimine Pd(II) and Ni(II) Alkyl Complexes: Identification of Problems Connected with Copolymerizations of These Monomers with Ethylene J. Am. Chem. Soc. 2005, 127, 5132 10.1021/ja045969s
41. Guironnet, D.; Roesle, P.; Rünzi, T.; Göttker-Schnetmann, I.; Mecking, S. Mechanistic Insights on the Copolymerization of Polar Vinyl Monomers with Neutral Ni(II) Catalysts J. Am. Chem. Soc. 2009, 131, 422 10.1021/ja808017n