Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes

Xiao-Lin Chen; Jie Gao; Heng Liao; Hai-Yang Gao; Qing Wu

doi:10.1007/s10118-018-2052-8

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Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes

Articles | Updated：2021-02-18

- Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes
- Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes
- Chinese Journal of Polymer Science 2018年36卷第2期页码：176-184
- Affiliations：
  
  School of Materials Science and Engineering, Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Guangdong Laboratory of High-performance Polymer Composites, Sun Yat-sen University, Guangzhou 510275, China
- Author bio：
  
  Hai-Yang Gao, E-mail gaohy@mail.sysu.edu.cn
- Funds：
- DOI：10.1007/s10118-018-2052-8
  中图分类号：
- 收稿：2017-08-28，
  
  录用：2017-9-28，
  
  网络首发：2017-11-21，
  
  纸质出版：2018-02-05
- Accepted：
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Xiao-Lin Chen, Jie Gao, Heng Liao, 等. Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes[J]. Chinese Journal of Polymer Science, 2018,36(2):176-184.

Xiao-Lin Chen, Jie Gao, Heng Liao, et al. Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes[J]. Chinese Journal of Polymer Science, 2018, 36(2): 176-184.
Xiao-Lin Chen, Jie Gao, Heng Liao, 等. Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes[J]. Chinese Journal of Polymer Science, 2018,36(2):176-184. DOI： 10.1007/s10118-018-2052-8.

Xiao-Lin Chen, Jie Gao, Heng Liao, et al. Synthesis, Characterization, and Catalytic Ethylene Oligomerization of Pyridine-imine Palladium Complexes[J]. Chinese Journal of Polymer Science, 2018, 36(2): 176-184. DOI： 10.1007/s10118-018-2052-8.

摘要

Abstract

Two neutral five-membered pyridine-imine palladium complexes with the bulky dibenzhydryl (CH(Ph)

) substituted aniline were synthesized and fully characterized by nuclear magnetic resonance (NMR) and X-ray crystal diffraction. Well-defined cationic palladium complexes were further obtained by treatment of chloromethylpalladium complexes with sodium tetrakis(3

5-bis(trifluoromethyl)phenyl)borate (NaBArF) in CH

CN. Cationic palladium complexes were capable of catalyzing ethylene oligomerization without any cocatalysts. The influences of catalyst structure

reaction temperature

and ethylene pressure on ethylene oligomerization were studied in detail. The introduction of bulky benzhydryl (CH(Ph)

) on the

ortho

position of the aniline moiety enhanced catalytic activity

thermal stability of the catalyst

and molecular weight of the obtained products. Highly branched oligomers with molecular weights of 600-800 g/mol and narrow polydispersities (1.03-1.12) were produced.

关键词

Keywords

references

L. K. Johnson , C. M. Killian , M. Brookhart . New Pd(Ⅱ)-and Ni(Ⅱ)-based catalysts for polymerization of ethylene and α -olefins . J. Am. Chem. Soc. , 1995 . 117 ( 23 ): 6414 - 6415 . DOI: 10.1021/ja00128a054 http://doi.org/10.1021/ja00128a054 .

L. K. Johnson , S. Mecking , M. Brookhart . Copolymerization of ethylene and propylene with functionalized vinyl monomers by palladium(Ⅱ) catalysts . J. Am. Chem. Soc. , 1996 . 118 ( 1 ): 267 - 268 . DOI: 10.1021/ja953247i http://doi.org/10.1021/ja953247i .

B. L. Small , M. Brookhart , A. M. A. Bennett . Highly active iron and cobalt catalysts for the polymerization of ethylene . J. Am. Chem. Soc. , 1998 . 120 ( 16 ): 4049 - 4050 . DOI: 10.1021/ja9802100 http://doi.org/10.1021/ja9802100 .

T. R. Younkin , E. F. Connor , J. I. Henderson , S. K. Friedrich , R. H. Grubbs , Bansleben , A. D. . Neutral, single-component nickel(Ⅱ) polyolefin catalysts that tolerate heteroatoms. . Science , 2000 . 287 ( 5452 ): 460 - 462 . DOI: 10.1126/science.287.5452.460 http://doi.org/10.1126/science.287.5452.460 .

E. Drent , R. V. Dijk , R. V. Ginkel , B. Oort , R. I. Pugh . Palladium catalysed copolymerisation of ethene with alkylacrylates: polar comonomer built into the linear polymer chain . Chem. Commun. , 2002 . 744 - 745 . .

H. L. Mu , L. Pan , D. P. Song , Y. S. Li . Neutral nickel catalysts for olefin homo-and copolymerization: relationships between catalyst structures and catalytic properties . Chem. Rev. , 2015 . 115 ( 22 ): 12091 - 12137 . DOI: 10.1021/cr500370f http://doi.org/10.1021/cr500370f .

L. H. Guo , S. Y. Dai , X. L. Sui , C. L. Chen . Palladium and nickel catalyzed chain walking olefin polymerization and copolymerization . ACS Catal. , 2016 . 6 ( 1 ): 428 - 441 . DOI: 10.1021/acscatal.5b02426 http://doi.org/10.1021/acscatal.5b02426 .

L. H. Guo , C. L. Chen . ( α -Diimine) palladium catalyzed ethylene polymerization and (co)polymerization with polar comonomers . Sci. China Chem. , 2015 . 58 ( 11 ): 1663 - 1673 . DOI: 10.1007/s11426-015-5433-7 http://doi.org/10.1007/s11426-015-5433-7 .

L. H. Guo , W. J. Liu , C. L. Chen . Late transition metal catalyzed α -olefin polymerization and copolymerization with polar monomers . Mater. Chem. Front. , 2017 . DOI: 10.1039/C7QM00321H http://doi.org/10.1039/C7QM00321H .

H. Y. Gao , F. S. Liu , H. B. Hu , F. M. Zhu , Q. Wu . Synthesis of bimodal polyethylene with unsymmetrical α -diimine nickel complexes: influence of ligand backbone and unsym-substituted aniline moiety . Chinese J. Polym. Sci. , 2013 . 31 ( 4 ): 563 - 573 . DOI: 10.1007/s10118-013-1251-6 http://doi.org/10.1007/s10118-013-1251-6 .

H. Y. Gao , L. X. Pei , Y. F. Li , J. K. Zhang , Q. Wu . Vinyl polymerization of norbornene with nickel catalysts bearing . J. Mol. Catal. A-Chem. , 2008 . 280 ( 1-2 ): 81 - 86 . DOI: 10.1016/j.molcata.2007.10.033 http://doi.org/10.1016/j.molcata.2007.10.033 .

H. Y. Gao , L. X. Pei , K. M. Song , Q. Wu . Styrene polymerization with novel anilido-imino nickel complexes/MAO catalytic system: catalytic behavior, microstructure of polystyrene and polymerization mechanism . Eur. Polym. J. , 2007 . 43 ( 3 ): 908 - 914 . DOI: 10.1016/j.eurpolymj.2006.11.026 http://doi.org/10.1016/j.eurpolymj.2006.11.026 .

Y. F. Li , L. Y. Wang , H. Y. Gao , F. M. Zhu , Q. Wu . Novel nickel(Ⅱ) complexes chelating β-diketiminate ligands: synthesis and simultaneous polymerization and oligomerization of ethylene . Appl. Organomet. Chem. , 2006 . 20 ( 7 ): 436 - 442 . DOI: 10.1002/(ISSN)1099-0739 http://doi.org/10.1002/(ISSN)1099-0739 .

H. Y. Gao , J. K. Zhang , Y. Chen , F. M. Zhu , Q. Wu . Vinyl-polymerization of norbornene with novel anilido-imino nickel complexes/methylaluminoxane: abnormal influence of polymerization temperature on molecular weight of polynorbornenes. . J. Mol. Catal. A-Chem. , 2005 . 240 ( 1-2 ): 178 - 185 . http://chem.scichina.com:8081/sciB/CN/abstract/abstract507453.shtml http://chem.scichina.com:8081/sciB/CN/abstract/abstract507453.shtml , .

L. Zhong , G. L. Li , G. D. Liang , H. Y. Gao , Q. Wu . Enhancing thermal stability and living fashion in α -diimine-nickel-catalyzed (co)polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone . Macromolecules , 2017 . 50 ( 7 ): 2675 - 2682 . DOI: 10.1021/acs.macromol.7b00121 http://doi.org/10.1021/acs.macromol.7b00121 .

S. H. Zhong , Y. X. Tan , L. Zhong , J. Gao , H. Liao , L. Jiang , H. Y. Gao , Q. Wu . Precision synthesis of ethylene and polar monomer copolymers by palladium-catalyzed living coordination copolymerization . Macromolecules , 2017 . 50 ( 15 ): 5661 - 5669 . DOI: 10.1021/acs.macromol.7b01132 http://doi.org/10.1021/acs.macromol.7b01132 .

H. Liao , L. Zhong , Z. F. Xiao , T. Zheng , H. Y. Gao , Q. Wu . α -Diamine nickel catalysts with nonplanar chelate rings for ethylene polymerization . Chem. Eur. J. , 2016 . 22 ( 39 ): 14048 - 14055 . DOI: 10.1002/chem.201602467 http://doi.org/10.1002/chem.201602467 .

H. B. Hu , D. R. Chen , H. Y. Gao , L. Zhong , Q. Wu . Amine-imine palladium catalysts for living polymerization of ethylene and copolymerization of ethylene with methyl acrylate: incorporation of acrylate units into the main chain and branch end . Polym. Chem. , 2016 . 7 529 - 537 . DOI: 10.1039/C5PY01743B http://doi.org/10.1039/C5PY01743B .

H. B. Hu , H. Y. Gao , D. R. Chen , G. L. Li , Y. X. Tan , G. D. Liang , F. M. Zhu , Q. Wu . Ligand-directed regioselectivity in amine-imine nickel-catalyzed 1-hexene polymerization . ACS Catal. , 2015 . 5 ( 1 ): 122 - 128 . DOI: 10.1021/cs501081a http://doi.org/10.1021/cs501081a .

J. Liu , D. R. Chen , H. Wu , Z. F. Xiao , H. Y. Gao , F. M. Zhu , Q. Wu . Polymerization of α -olefins using a camphyl α -diimine nickel catalyst at elevated temperature . Macromolecules , 2014 . 47 ( 10 ): 3325 - 3331 . DOI: 10.1021/ma5004634 http://doi.org/10.1021/ma5004634 .

H. B. Hu , L. Zhang , H. Y. Gao , F. M. Zhu , Q. Wu. . Design of thermally stable amine-imine nickel catalyst precursors for living polymerization of ethylene: effect of ligand substituents on catalytic behavior and polymer properties . Chem. Eur. J. , 2014 . 20 ( 11 ): 3225 - 3233 . DOI: 10.1002/chem.201303813 http://doi.org/10.1002/chem.201303813 .

H. Y. Gao , Y. Liu , G. L. Li , Z. F. Xiao , G. D. Liang , Q. Wu . Catalytic synthesis of polyethylene-block-polynorbornene copolymers using a living polymerization nickel catalyst . Polym. Chem. , 2014 . 5 6012 - 6018 . DOI: 10.1039/C4PY00701H http://doi.org/10.1039/C4PY00701H .

H. Y. Gao , G. L. Li , Z. L. Hu , Z. F. Xiao , G. D. Liang , Q. Wu. . Synthesis of amphiphilic polyethylene- b -poly(l-glutamate) block copolymers with vastly different solubilities and their stimuli-responsive polymeric micelles in aqueous solution . Polymer , 2014 . 55 4593 - 4600 . DOI: 10.1016/j.polymer.2014.07.019 http://doi.org/10.1016/j.polymer.2014.07.019 .

J. A. Deng , H. Y. Gao , F. M. Zhu , Q. Wu . Synthesis and structure of imine- n -heterocyclic carbene palladium complexes and their catalytic behavior in norbornene polymerization . Organometallics , 2013 . 32 ( 16 ): 4507 - 4515 . DOI: 10.1021/om400268y http://doi.org/10.1021/om400268y .

H. Y. Gao , Y. Tang , H. B. Hu , Q. R. Guan , X. B. Shi , F. M. Zhu , Q. Wu . Synthesis of amphiphilic copolymers with a dendritic polyethylene core and poly(ethylene oxide) arms and their self-assembled nanostructures . Polym. Chem. , 2013 . 4 1107 - 1114 . DOI: 10.1039/C2PY20831H http://doi.org/10.1039/C2PY20831H .

H. Y. Gao , Z. L. Hu , Q. R. Guan , Y. Liu , F. M. Zhu , Q. Wu . Synthesis and thermoreversible gelation of coil-helical polyethylene-block-poly(gamma-benzyl-L-glutamate) diblock copolymer . Polymer , 2013 . 54 4923 - 4929 . DOI: 10.1016/j.polymer.2013.06.055 http://doi.org/10.1016/j.polymer.2013.06.055 .

H. Y. Gao , H. B. Hu , F. M. Zhu , Q. Wu . A thermally robust amine-imine nickel catalyst precursor for living polymerization of ethylene above room temperature . Chem. Commun. , 2012 . 48 3312 - 3314 . DOI: 10.1039/c2cc17154f http://doi.org/10.1039/c2cc17154f .

J. D. Azoulay , H. Y. Gao , Z. A. Koretz , G. Kehr , G. Erker , F. Shimizu , G. B. Galland , G. C. Bazan . Propylene polymerization with alpha-keto-beta-diimine initiators proceeds via enantiomorphic site control . Macromolecules , 2012 . 45 4487 - 4493 . DOI: 10.1021/ma300504j http://doi.org/10.1021/ma300504j .

X. B. Shi , Y. Zhao , H. Y. Gao , L. Zhang , F. M. Zhu , Q. Wu . Synthesis of hyperbranched polyethylene amphiphiles by chain walking polymerization in tandem with RAFT polymerization and supramolecular self-assembly vesicles . Macromol. Rapid Commun. , 2012 . 33 ( 5 ): 374 - 379 . DOI: 10.1002/marc.201100825 http://doi.org/10.1002/marc.201100825 .

H. Y. Gao , X. F. Liu , Y. Tang , J. Pan , Q. Wu . Living/controlled polymerization of 4-methyl-1-pentene with α -diimine nickel-diethylaluminium chloride: effect of alkylaluminium cocatalysts . Polym. Chem. , 2011 . 2 1398 - 1403 . DOI: 10.1039/c1py00052g http://doi.org/10.1039/c1py00052g .

H. Y. Gao , J. Pan , L. H. Guo , D. J. Xiao , Q. Wu . Polymerization of 4-methyl-1-pentene catalyzed by-diimine nickel catalysts: living/controlled behavior, branch structure, and mechanism . Polymer , 2011 . 52 130 - 137 . DOI: 10.1016/j.polymer.2010.11.008 http://doi.org/10.1016/j.polymer.2010.11.008 .

L. H. Guo , H. Y. Gao , Q. Wu . Complex branched polyolefin generated from quasi-living polymerization of 4-methyl-1-pentene catalyzed by α -diimine palladium catalyst . Macromol. Chem. Phys. , 2011 . 212 ( 18 ): 2029 - 2035 . DOI: 10.1002/macp.v212.18 http://doi.org/10.1002/macp.v212.18 .

L. H. Guo , H. Y. Gao , Q. R. Guan , H. B. Hu , J. A. Deng , J. Liu , S. F. Liu , Q. Wu . Substituent effects of the backbone in α -diimine palladium catalysts on homo-and copolymerization of ethylene with methyl acrylate . Organometallics , 2012 . 31 ( 17 ): 6054 - 6062 . DOI: 10.1021/om300380b http://doi.org/10.1021/om300380b .

F. S. Liu , H. B. Hu , Y. Xu , L. H. Guo , S. B. Zai , K. M. Song , H. Y. Gao , L. Zhang , F. M. Zhu , Q. Wu . Thermostable α -diimine nickel(Ⅱ) catalyst for ethylene polymerization: effects of the substituted backbone structure on catalytic properties and branching structure of polyethylene . Macromolecules , 2009 . 42 ( 20 ): 7789 - 7796 . DOI: 10.1021/ma9013466 http://doi.org/10.1021/ma9013466 .

Z. F. Huang , K. M. Song , F. S. Liu , J. M. Long , H. Hu , H. Y. Gao , Q. Wu . Synthesis and characterization of a series of 2-aminopyridine nickel(Ⅱ) complexes and their catalytic properties toward ethylene polymerization . J. Polym. Sci., Part A: Polym. Chem. , 2008 . 46 ( 5 ): 1618 - 1628 . DOI: 10.1002/(ISSN)1099-0518 http://doi.org/10.1002/(ISSN)1099-0518 .

S. B. Zai , H. Y. Gao , Z. F. Huang , H. B. Hu , H. Wu , Q. Wu . Substituent effects of pyridine-amine nickel catalyst precursors on ethylene polymerization . ACS Catal. , 2012 . 2 ( 3 ): 433 - 440 . DOI: 10.1021/cs200593c http://doi.org/10.1021/cs200593c .

Y. Zhao , H. Y. Gao , L. Zhang , F. M. Zhu , Q. Wu . Thermo-and pH-sensitive polyethylene-based diblock and triblock copolymers: synthesis and self-assembly in aqueous solution . J. Mater. Chem. , 2012 . 22 5737 - 5745 . DOI: 10.1039/c2jm16197d http://doi.org/10.1039/c2jm16197d .

S. B. Zai , F. S. Liu , H. Y. Gao , C. Li , G. Y. Zhou , S. Cheng , L. H. Guo , L. Zhang , F. M. Zhu , Q. Wu . Longstanding living polymerization of ethylene: substituent effect on bridging carbon of 2-pyridinemethanamine nickel catalysts . Chem. Commun. , 2010 . 46 4321 - 4323 . DOI: 10.1039/c000176g http://doi.org/10.1039/c000176g .

L. H. Guo , H. Y. Gao , L. Zhang , F. M. Zhu , Q. Wu . An unsymmetrical iron(Ⅱ) bis(imino)pyridyl catalyst for ethylene polymerization: effect of a bulky ortho substituent on the thermostability and molecular weight of polyethylene . Organometallics , 2010 . 29 ( 9 ): 2118 - 2125 . DOI: 10.1021/om9010356 http://doi.org/10.1021/om9010356 .

C. Bianchini , G. Giambastiani , L. Luconi , A. Meli . Olefin oligomerization, homopolymerization and copolymerization by late transition metals supported by (imino)pyridine ligands . Coordin. Chem. Rev. , 2010 . 254 ( 5-6 ): 431 - 455 . DOI: 10.1016/j.ccr.2009.07.013 http://doi.org/10.1016/j.ccr.2009.07.013 .

X. B. Tang , W. H. Sun , T. L. Gao , J. X. Hou , J. T. Chen , W. Chen . Nickel(Ⅱ) complexes bearing 2-ethylcarboxylate-6-iminopyridyl ligands: synthesis, structures and their catalytic behavior for ethylene oligomerization and polymerization . J. Organomet. Chem. , 2005 . 690 ( 6 ): 1570 - 1580 . DOI: 10.1016/j.jorganchem.2004.12.027 http://doi.org/10.1016/j.jorganchem.2004.12.027 .

T. V. Laine , U. Piironen , K. Lappalainen , M. Klinga , L. M. Aitola . Nickel(Ⅱ) complexes bearing 2-ethylcarboxylate-6-iminopyridyl ligands: synthesis, structures and their catalytic behavior for ethylene oligomerization and polymerization . J. Organomet. Chem. , 2000 . 606 ( 2 ): 112 - 124 . DOI: 10.1016/S0022-328X(00)00291-6 http://doi.org/10.1016/S0022-328X(00)00291-6 .

S. Y. Dai , X. L. Sui , C. L. Chen . Synthesis of high molecular weight polyethylene using iminopyridyl nickel catalysts . Chem. Commun. , 2016 . 52 9113 - 9116 . DOI: 10.1039/C6CC00457A http://doi.org/10.1039/C6CC00457A .

S. Y. Dai , C. L. Chen . Direct synthesis of functionalized high-molecular-weight polyethylene by copolymerization of ethylene with polar monomers . Angew. Chem. Int. Ed. , 2016 . 55 ( 42 ): 13281 - 13285 . DOI: 10.1002/anie.201607152 http://doi.org/10.1002/anie.201607152 .

S. Y. Dai , S. X. Zhou , W. Zhang , C. L. Chen . Systematic investigations of ligand steric effects on α -diimine palladium catalyzed olefin polymerization and copolymerization . Macromolecules , 2016 . 49 ( 23 ): 8855 - 8862 . DOI: 10.1021/acs.macromol.6b02104 http://doi.org/10.1021/acs.macromol.6b02104 .

X. L. Sui , C. W. Hong , W. M. Pang , C. L. Chen . Unsymmetrical α -diimine palladium catalysts and their properties in olefin (co)polymerization . Mater. Chem. Front. , 2017 . 1 967 - 972 . DOI: 10.1039/C6QM00235H http://doi.org/10.1039/C6QM00235H .

L. H. Guo , C. Zou , S. Y. Dai , C. L. Chen . Direct synthesis of branched carboxylic acid functionalized poly(1-octene) by α -diimine palladium catalysts . Polymers , 2017 . 9 ( 4 ): 122 DOI: 10.3390/polym9040122 http://doi.org/10.3390/polym9040122 .

X. H. Hu , S. Y. Dai , C. L. Chen . Ethylene polymerization by salicylaldimine nickel(Ⅱ) complexes containing a dibenzhydryl moiety . Dalton Trans. , 2016 . 45 1496 - 1503 . DOI: 10.1039/C5DT04408A http://doi.org/10.1039/C5DT04408A .

J. L. Rhinehart , L. A. Brown , B. K. Long . A robust Ni(Ⅱ) α -diimine catalyst for high temperature ethylene polymerization . J. Am. Chem. Soc. , 2013 . 136 16316 - 16319 . http://pubs.acs.org/doi/full/10.1021/acs.chemrev.6b00314?src=recsys http://pubs.acs.org/doi/full/10.1021/acs.chemrev.6b00314?src=recsys , .

S. Y. Dai , X. L. Sui , C. L. Chen . 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 ( 34 ): 9948 - 9953 . DOI: 10.1002/anie.201503708 http://doi.org/10.1002/anie.201503708 .

W. H. Sun , S. J. Song , B. X. Li , C. Redshaw , X. Hao , Y. S. Li , F. S. Wang . Ethylene polymerization by 2-iminopyridylnickel halide complexes: synthesis, characterization and catalytic influence of the benzhydryl group . Dalton Trans. , 2012 . 41 11999 - 12010 . DOI: 10.1039/c2dt30989k http://doi.org/10.1039/c2dt30989k .

S. P. Meneghetti , P. J. Lutz , J. Kress . Oligomerization of olefins catalyzed by new cationic palladium(Ⅱ) complexes containing an unsymmetrical α -diimine ligand . Organometallics , 1999 . 18 ( 15 ): 2734 - 2737 . DOI: 10.1021/om990165k http://doi.org/10.1021/om990165k .

G. S. Nyamato , S. O. Ojwach , M. P. Akerman . Potential hemilabile (imino)pyridine palladium(Ⅱ) complexes as selective ethylene dimerization catalysts: an experimental and theoretical approach . Organometallics , 2015 . 34 ( 23 ): 5647 - 5657 . DOI: 10.1021/acs.organomet.5b00860 http://doi.org/10.1021/acs.organomet.5b00860 .

D. Bezier , O. Daugulis , M. Brookhart . Oligomerization of ethylene using a diphosphine palladium catalyst . Organometallics , 2017 . 36 ( 2 ): 443 - 447 . DOI: 10.1021/acs.organomet.6b00850 http://doi.org/10.1021/acs.organomet.6b00850 .

C. J. Stephenson , J. P. Mcinnis , C. L. Chen , M. P. Weberski , A. Motta , M. Delferro , T. J. Marks . Ni(Ⅱ) phenoxyiminato olefin polymerization catalysis: striking coordinative modulation of hyperbranched polymer microstructure and stability by a proximate sulfonyl group . ACS Catal. , 2014 . 4 ( 3 ): 999 - 1003 . DOI: 10.1021/cs500114b http://doi.org/10.1021/cs500114b .

T. Wiedemann , G. Voit , A. Tchernook , P. Roesel , I. G. Schnetmann , S. Mecking . Monofunctional hyperbranched ethylene oligomers . J. Am. Chem. Soc. , 2014 . 136 ( 5 ): 2078 - 2085 . DOI: 10.1021/ja411945n http://doi.org/10.1021/ja411945n .

S. Y. Jie , D. H. Zhang , T. Z. Zhang , W. H. Sun , J. T. Chen , Q. Ren , D. B. Liu , G. Zheng , W. J. Chen . Bridged bispyridinylimino dinickel(Ⅱ) complexes: syntheses, characterization, ethylene oligomerization and polymerization . Organomet. Chem. , 2005 . 690 ( 7 ): 1739 - 1749 . DOI: 10.1016/j.jorganchem.2005.01.029 http://doi.org/10.1016/j.jorganchem.2005.01.029 .

P. Xiang , Z. B. Ye , R. Subramanian . Synthesis and characterization of low-and medium-molecular-weight hyperbranched polyethylenes by chain walking ethylene polymerization with Pd-diimine catalysts . Polymer , 2011 . 52 ( 22 ): 5027 - 5039 . DOI: 10.1016/j.polymer.2011.09.010 http://doi.org/10.1016/j.polymer.2011.09.010 .

S. Ray , P. V. C. Rao , N. V. V. Choudary . Poly- α -olefin-based synthetic lubricants: a short review on various synthetic routes . Lubr. Sci. , 2012 . 24 23 - 44 . DOI: 10.1002/ls.v24.1 http://doi.org/10.1002/ls.v24.1 .

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