a.Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Pertrochemical Engineering, Changzhou University, Changzhou 213164, China
b.Chinese Academy of Sciences Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China
E-mail wangfuzhou1718@126.com (F.Z.W.)
E-mail changle@ustc.edu.cn (C.L.C)
收稿:2017-08-17,
录用:2017-9-7,
网络首发:2017-11-01,
纸质出版:2018-02-05
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Fu-Zhou Wang, Su-Su Tian, Rui-Ping Li, 等. Ligand Steric Effects on Naphthyl-
Fu-Zhou Wang, Su-Su Tian, Rui-Ping Li, et al. Ligand Steric Effects on Naphthyl-
Fu-Zhou Wang, Su-Su Tian, Rui-Ping Li, 等. Ligand Steric Effects on Naphthyl-
Fu-Zhou Wang, Su-Su Tian, Rui-Ping Li, et al. Ligand Steric Effects on Naphthyl-
Naphthyl-
α
-diimine nickel complexes with systematically varied ligand sterics
activated by modified methylaluminoxane (MMAO)
were tested in the polymerization of higher
α
-olefin (1-hexene
1-decene and 1-hexadecene) under suitable conditions. The polymerization results indicated the possibility of precise microstructure control
depending on catalyst structure
polymerization temperature
monomer concentration and types of monomers
which in turn strongly affects the resultant polymer properties. Naphthyl-
α
-diimine nickel complex bearing chiral bulky
sec
-phenethyl groups in the
o
-naphthyl position showed good catalytic activity
and resulted in branched polymers (42-88/1000C) with high molecular weights (
M
n
:(4.3-15.2)×10
4
g·mol
-1
) and narrow molecular weight distribution (
M
w
/
M
n
=1.13-1.29
RT)
which suggested a living polymerization. The increasing steric hindrance of catalyst leads to enhance insertion for 2
1-insertion of
α
-olefin and the chain-walking reaction.
C. M. Killian , D. J. Tempel , L. K. Johnson , M. Brookhart . Living polymerization of α -olefins Ni(Ⅱ)- α -diimine catalysts . synthesis of new block polymers based on α -olefins. J. Am. Chem. Soc. , 1996 . 118 ( 46 ): 11664 - 11665 . .
D. P. Gates , S. A. Svejda , E. Oñate , C. M. Killian , L. K. Johnson , P. S. White , M. Brookhart . Synthesis of branched polyethylene using ( α -diimine)nickel(Ⅱ) catalysts:influence of temperature, ethylene pressure, and ligand structure on polymer properties . Macromolecules , 2000 . 33 ( 7 ): 2320 - 2334 . DOI: 10.1021/ma991234+ http://doi.org/10.1021/ma991234+ .
S. D. Ittel , L. K. Johnson , M. Brookhart . Late-metal catalysts for ethylene homo-and copolymerization . Chem. Rev. , 2000 . 100 ( 4 ): 1169 - 1204 . DOI: 10.1021/cr9804644 http://doi.org/10.1021/cr9804644 .
Z. Guan , C. S. Popeney . Recent progress in late transition metal α -diimine catalysts for olefin polymerization . Top. Organomet. Chem. , 2009 . 26 179 - 220 . DOI: 10.1007/978-3-540-87751-6 http://doi.org/10.1007/978-3-540-87751-6 .
Z. Dong , Z. Ye . Hyperbranched polyethylenes by chain walking polymerization:synthesis, properties, functionalization, and applications . Polym. Chem. , 2012 . 3 ( 2 ): 286 - 301 . DOI: 10.1039/C1PY00368B http://doi.org/10.1039/C1PY00368B .
D. Takeuchi . Stereo-controlled synthesis of polyolefins with cycloalkane groups by using late transition metals . Polym. J. , 2012 . 44 ( 9 ): 919 - 928 . DOI: 10.1038/pj.2012.27 http://doi.org/10.1038/pj.2012.27 .
M. P. Weberski , C. Chen , M. Delferro , C. Zuccaccia , A. Macchioni , T. J. Marks . Suppression of β -hydride chain transfer in nickel(Ⅱ)-catalyzed ethylene polymerization via weak fluorocarbon ligandproduct interactions . Organometallics , 2012 . 31 ( 9 ): 3773 - 3789 . DOI: 10.1021/om3002735 http://doi.org/10.1021/om3002735 .
X. L. Sui , S. Y. Dai , C. L. Chen . Ethylene polymerization and copolymerization with polar monomers by cationic phosphine phosphonic amide palladium complexes . ACS Catal. , 2015 . 5 ( 10 ): 5932 - 5937 . DOI: 10.1021/acscatal.5b01490 http://doi.org/10.1021/acscatal.5b01490 .
M. Chen , B. P. Yang , C. L. Chen . Redox-controlled olefin (co)polymerization catalyzed by ferrocene-bridged phosphinesulfonate palladium complexes . Angew. Chem. Int. Ed. , 2015 . 54 ( 51 ): 15520 - 15524 . DOI: 10.1002/anie.201507274 http://doi.org/10.1002/anie.201507274 .
M. Chen , W. P. Zou , Z. G. Cai , C. L. Chen . Norbornene homopolymerization and copolymerization with ethylene by phosphine-sulfonate nickel catalysts . Polym. Chem. , 2015 . 6 ( 14 ): 2669 - 2676 . DOI: 10.1039/C5PY00010F http://doi.org/10.1039/C5PY00010F .
T. Liang , C. L. Chen . Side-arm control in phosphine-sulfonate palladium-and nickel-catalyzed ethylene polymerization and copolymerization . Organometallics , 2017 . 36 ( 12 ): 2338 - 2344 . DOI: 10.1021/acs.organomet.7b00294 http://doi.org/10.1021/acs.organomet.7b00294 .
M. Chen , C. L. Chen . Rational design of high-performance phosphine sulfonate nickel catalysts for ethylene polymerization and copolymerization with polar monomers . ACS Catal. , 2017 . 7 ( 2 ): 1308 - 1312 . DOI: 10.1021/acscatal.6b03394 http://doi.org/10.1021/acscatal.6b03394 .
Z. Jian , L. Falivene , G. Boffa , S. O. Sánchez , L. Caporaso , A. Grassi , S. Mecking . Direct synthesis of telechelic polyethylene by selective insertion polymerization . Angew. Chem. , 2016 . 55 ( 46 ): 14378 - 14383 . DOI: 10.1002/anie.v55.46 http://doi.org/10.1002/anie.v55.46 .
Y. Ota , S. Ito , M. Kobayashi , S. Kitade , K. Sakata , T. Tayano , K. Nozaki . Crystalline isotactic polar polypropylene from the palladium-catalyzed copolymerization of propylene and polar monomers . Angew. Chem. , 2016 . 128 ( 26 ): 7631 - 7635 . DOI: 10.1002/ange.201600819 http://doi.org/10.1002/ange.201600819 .
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 , 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 .
D. F. Zhang , E. T. Nadres , M. Brookhart , O. Daugulis . Synthesis of highly branched polyethylene using "sandwich" (8-p-tolyl naphthyl α -diimine) nickel(Ⅱ) catalysts . Organometallics , 32 ( 18 ): 5136 - 5143 . DOI: 10.1021/om400704h http://doi.org/10.1021/om400704h .
T. Vaidya , K. Klimovica , A. M. LaPointe , I. Keresztes , E. B. Lobkovsky , O. Daugulis , Coates , W. G. . Secondary alkene insertion and precision chain-walking:a new route to semicrystalline "polyethylene" from α -olefins by combining two rare catalytic events. . J. Am. Chem. Soc. , 2014 . 136 ( 20 ): 7213 - 7216 . DOI: 10.1021/ja502130w http://doi.org/10.1021/ja502130w .
C. Chen , S. Luo , R. F. Jordan . Multiple insertion of a silyl vinyl ether by ( α -diimine)PdMe + species . J. Am. Chem. Soc. , 2008 . 130 ( 39 ): 12892 - 12893 . DOI: 10.1021/ja8056858 http://doi.org/10.1021/ja8056858 .
C. Chen , S. Luo , R. F. Jordan . Cationic polymerization and insertion chemistry in the reactions of vinyl ethers with ( α -diimine) PdMe+ species . J. Am. Chem. Soc. , 2010 . 132 ( 14 ): 5273 - 5284 . DOI: 10.1021/ja100491y http://doi.org/10.1021/ja100491y .
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. , 2015 . 127 ( 34 ): 10086 - 10091 . DOI: 10.1002/ange.201503708 http://doi.org/10.1002/ange.201503708 .
S. Y. Dai , C. L. Chen . Direct synthesis of functionalized highmolecular-weight polyethylene bycopolymerizationofethylene with polar monomers . Angew. Chem. Int. Ed. , 2016 . 55 ( 42 ): 13281 - 13285 . DOI: 10.1002/anie.201607152 http://doi.org/10.1002/anie.201607152 .
M. Li , X. B. Wang , Y. Luo , C. L. Chen . A secondcoordination-sphere strategy to modulate nickel-and palladium-catalyzed olefin polymerization and copolymerization . Angew. Chem. Int. Ed. , 2017 . 56 ( 38 ): 11604 - 11609 . DOI: 10.1002/anie.v56.38 http://doi.org/10.1002/anie.v56.38 .
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 .
K. Lian , Y. Zhu , W. Li , S. Y. Dai , C. L. Chen . Direct synthesis of thermoplastic polyolefin elastomers from nickel-catalyzed ethylene polymerization . Macromolecules , 2017 . 50 ( 16 ): 6074 - 6080 . DOI: 10.1021/acs.macromol.7b01087 http://doi.org/10.1021/acs.macromol.7b01087 .
R. K. Wang , M. H. Zhao , C. L. Chen . Influence of ligand second coordination sphere effects on the olefin (co)polymerization properties of α -diimine Pd(Ⅱ) catalysts . Polym. Chem., , 2016 . 7 ( 23 ): 3933 - 3938 . DOI: 10.1039/C6PY00750C http://doi.org/10.1039/C6PY00750C .
L. H. Guo , S. Y. Dai , C. L. Chen . Investigations of the ligand electronic effects on α -diimine nickel(Ⅱ) catalyzed ethylene polymerization . Polymers , 2016 . 8 ( 2 ): 37 DOI: 10.3390/polym8020037 http://doi.org/10.3390/polym8020037 .
L. Zhu , Z. S. Fu , H. J. Pan , W. Feng , C. L. Chen , Z. Q. Fan . Synthesis and application of binuclear α -diimine nickel/palladium catalysts with a conjugated backbone . Dalton Trans. , 2014 . 43 ( 7 ): 2900 - 2906 . DOI: 10.1039/C3DT51782A http://doi.org/10.1039/C3DT51782A .
Y. N. Na , D. Zhang , C. L. Chen . Modulating the polyolefin properties through the incorporation of nitrogen-containing polar monomers . Polym. Chem. , 2017 . 8 ( 15 ): 2405 - 2409 . DOI: 10.1039/C7PY00127D http://doi.org/10.1039/C7PY00127D .
W. Zou , C. Chen . Influence of backbone substituents on the ethylene (co)polymerization properties of α -diimine Pd(Ⅱ) and Ni(Ⅱ) catalysts . Organometallics , 2016 . 35 ( 11 ): 1794 - 1801 . DOI: 10.1021/acs.organomet.6b00202 http://doi.org/10.1021/acs.organomet.6b00202 .
F. Z. Wang , an Yu , J , Li Q. S. C.; , R. Tanaka , Y. Nakayama , T. Shiono . New nickel(Ⅱ) diimine complexes bearing phenyl and sec-phenethyl groups:synthesis, characterization and ethylene polymerization, behaviour . Appl. Organometal. Chem. , 2014 . 28 ( 7 ): 477 - 483 . DOI: 10.1002/aoc.v28.7 http://doi.org/10.1002/aoc.v28.7 .
F. Z. Wang , R. Tanaka , Q. S. Li , J. C. Yuan , Y. Nakayama , T. Shiono . Synthesis and application of α -diimine Ni(Ⅱ) and Pd(Ⅱ) complexes with bulky steric groups to polymerization of ethylene and methyl methacrylate . J. Mol. Catal. A Chem. , 2015 . 398 ( 398 ): 231 - 240 . .
X. H. Hu , S. Y. Dai , C. L. Chen . Ethylene polymerization by salicylaldimine nickel(Ⅱ) complexes containing a dibenzhydryl moiety . Dalton Trans. , 2016 . 45 ( 4 ): 1496 - 1503 . DOI: 10.1039/C5DT04408A http://doi.org/10.1039/C5DT04408A .
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 ( 5 ): 967 - 972 . DOI: 10.1039/C6QM00235H http://doi.org/10.1039/C6QM00235H .
R. K. Wang , X. L. Sui , W. M. Pang , C. L. Chen . Ethylene polymerization by xanthene-bridged dinuclear α -diimine NiⅡ complexes . ChemCatChem , 2016 . 8 ( 2 ): 434 - 440 . DOI: 10.1002/cctc.201501041 http://doi.org/10.1002/cctc.201501041 .
Y. N. Na , X. Wang , K. Lian , Y. Zhu , W. Li , Y. Luo , C. L. Chen . Dinuclear α -diimine Ni Ⅱ and Pd Ⅱ complexes that catalyze ethylene polymerization and copolymerization . ChemCatChem. , 2017 . 9 ( 6 ): 1062 - 1066 . DOI: 10.1002/cctc.v9.6 http://doi.org/10.1002/cctc.v9.6 .
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 . 135 ( 44 ): 16316 - 16319 . DOI: 10.1021/ja408905t http://doi.org/10.1021/ja408905t .
B. K. Long , J. M. Eagan , M. Mulzer , G. W. Coates . Semi-crystalline polar polyethylene:ester-functionalized linear polyolefins enabled by a functional-group-tolerant, cationic nickel catalyst . Angew. Chem. Int. Ed. , 2016 . 55 ( 25 ): 7106 - 7110 . DOI: 10.1002/anie.201601703 http://doi.org/10.1002/anie.201601703 .
Z. Chen , W. Liu , O. Daugulis , M. Brookhart . Mechanistic studies of Pd(Ⅱ)-catalyzed copolymerization of ethylene and vinylalkoxysilanes:Evidence for a β -silyl elimination chain transfer mechanism . J. Am. Chem. Soc. , 2016 . 138 ( 49 ): 16120 - 16129 . DOI: 10.1021/jacs.6b10462 http://doi.org/10.1021/jacs.6b10462 .
S. Talebnezhad , S. Pourmahdian . Multi-walled carbon nanotubes as a ligand in nickel α -diimine based ethylene polymerization . Chinese J. Polym. Sci. , 2015 . 33 ( 10 ): 1389 - 1403 . DOI: 10.1007/s10118-015-1696-x http://doi.org/10.1007/s10118-015-1696-x .
B. Liu , M. Z. Fang , S. Y. Jie , Z. Y. Bu , B. G. Li . Nickel(Ⅱ) α -diimine catalysts with carboxyl groups for ethylene oligomerization and polymerization . Chinese J. Polym. Sci. , 2016 . 34 ( 2 ): 221 - 228 . DOI: 10.1007/s10118-016-1734-3 http://doi.org/10.1007/s10118-016-1734-3 .
F. S. Liu , H. Y. Gao , Z. L. Hu , H. B. Hu , F. M. Zhu , Q. Wu . Poly(1-hexene) with long methylene sequences and controlled branches obtained by a thermostable α -diimine nickel catalyst with bulky camphyl backbone . J. Polym. Sci., Part A:Polym. Chem. , 2012 . 50 ( 18 ): 3859 - 3866 . DOI: 10.1002/pola.v50.18 http://doi.org/10.1002/pola.v50.18 .
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 .
A. E. Cherian , J. M. Rose , E. B. Lobkovsky , G. W. J. Coates . A C 2 -symmetric, living α -diimine Ni(Ⅱ) catalyst:regioblock copolymers from propylene . J. Am. Chem. Soc. , 2005 . 127 ( 40 ): 13770 - 13771 . DOI: 10.1021/ja0540021 http://doi.org/10.1021/ja0540021 .
J. M. Rose , A. E. Cherian , G. W. Coates . Living polymerization of α -olefins with an α -diimine Ni(Ⅱ) catalyst:formation of well-defined ethylene-propylene copolymers through controlled chain-walking . J. Am. Chem. Soc. , 2006 . 128 ( 13 ): 4186 - 4187 . DOI: 10.1021/ja058183i http://doi.org/10.1021/ja058183i .
S. Y. Dai , X. L. Sui , C. L. Chen . Synthesis of high molecular weight polyethylene using iminopyridyl nickel catalysts . Chem. Commun. , 2016 . 52 ( 58 ): 9113 - 9116 . DOI: 10.1039/C6CC00457A http://doi.org/10.1039/C6CC00457A .
F. Z. Wang , R. Tanaka , Z. G. Cai , Y. Nakayama , T. Shiono . Precision chain-walking polymerization of trans -4-octene catalyzed by α -diimine nickel(Ⅱ) catalysts bearing ortho-sec -phenethyl groups . Macromol. Rapid Commun. , 2016 . 37 ( 16 ): 1375 - 1381 . DOI: 10.1002/marc.v37.16 http://doi.org/10.1002/marc.v37.16 .
F. Z. Wang , J. C. Yuan , F. Y. Song , J. Li , Z. Jia , B. N. Yuan . New chiral α -diimine nickel(Ⅱ) complexes bearing ortho-sec -phenethyl groups for ethylene polymerization . Appl. Organomet. Chem. , 2013 . 27 ( 6 ): 319 - 327 . DOI: 10.1002/aoc.v27.6 http://doi.org/10.1002/aoc.v27.6 .
J. C. Yuan , F. Z. Wang , W. B. Xu , T. J. Mei , J. Li , B. N. Yuan , F. Y. Song , Z. Jia . Chiral naphthyl- α -diimine nickel(Ⅱ) catalysts bearing sec -phenethyl groups:chain-walking polymerization of ethylene at high temperature and stereoselective polymerization of methyl methacrylate at low temperature . Organometallics , 2013 . 32 ( 14 ): 3960 - 3968 . DOI: 10.1021/om400433t http://doi.org/10.1021/om400433t .
E. F. McCord , S. J. McLain , L. T. J. Nelson , S. D. Ittel , D. Tempel , C. M. Killian , L. K. Johnson , M. Brookhart . 13 C-NMR analysis of α -olefin enchainment in poly( α -olefins) produced with nickel and palladium α -diimine catalysts . Macromolecules , 2007 . 40 ( 3 ): 410 - 420 . DOI: 10.1021/ma061547m http://doi.org/10.1021/ma061547m .
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