Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with <italic style="font-style: italic">para</italic>-Chlorostyrene

Yan-Qing Li; Jian Zhou; Ru Xiao; Zheng-Guo Cai

doi:10.1007/s10118-020-2400-3

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Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene

ARTICLE | Updated：2020-04-02

- Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene
- Chinese Journal of Polymer Science Vol. 38, Issue 9, Pages: 941-949(2020)
- Affiliations：
  
  a.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, Shanghai 201620, China
  b.College of Biological and Chemical Engineering, Guangxi University of Science and Technology, Liuzhou 545006, China
- Author bio：
  
  xiaoru@dhu.edu.cn (R.X.)
  caizg@dhu.edu.cn (Z.G.C.)
- Funds：
- DOI：10.1007/s10118-020-2400-3
  CLC：
- Received：10 January 2020，
  
  Revised：2020-2-3，
  
  Accepted：04 February 2020，
  
  Online First：02 April 2020，
  
  Published：2020-09
- Accepted：
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Li, Y. Q.; Zhou, J.; Xiao, R.; Cai, Z. G. Quinolinyl imidazolidin-2-imine nickel catalyzed efficient copolymerization of norbornene with , para,-chlorostyrene. Chinese J. Polym. Sci. 2020, 38, 941–949

Yan-Qing Li, Jian Zhou, Ru Xiao, et al. Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene[J]. Chinese Journal of Polymer Science, 2020, 38(9): 941-949. DOI: 10.1007/s10118-020-2400-3.
Li, Y. Q.; Zhou, J.; Xiao, R.; Cai, Z. G. Quinolinyl imidazolidin-2-imine nickel catalyzed efficient copolymerization of norbornene with , para,-chlorostyrene. Chinese J. Polym. Sci. 2020, 38, 941–949 DOI： 10.1007/s10118-020-2400-3.

Yan-Qing Li, Jian Zhou, Ru Xiao, et al. Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene[J]. Chinese Journal of Polymer Science, 2020, 38(9): 941-949. DOI: 10.1007/s10118-020-2400-3. DOI：

摘要

Abstract

A series of novel quinolinyl imidazolidin-2-imine nickel complexes with different substituents on the imidazolidin-2-imine ligand were synthesized and characterized. The complexes in the presence of methylaluminoxane (MAO) as a cocatalyst catalyzed the copolymerization of norbornene (N) and styrene (S) or

para

-chlorostyrene (CS) with high activity (up to 1070 kg·mol

−1

·h

−1

). The installation of sterically bulky substituents on the imidazolidine-2-imine ligand was effective for the increase of the molecular weight and the comonomer content

affording high molecular weight copolymers with tunable CS content (0.57 mol%−11.7 mol%)

in which the existence of Cl group can provide reaction site for the further functionalization of copolymers as well as the synthesis of graft or cross-linked polymers. The linear relationship between the comonomer content and the glass transition temperature of the copolymers and the monomer reactivity ratios in the copolymerization indicated the formation of the expected functionalized cyclic olefin copolymers (COC).

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Khanarian, G.; Celanese, H. . Optical properties of cyclic olefin copolymers . Opt. Eng. , 2001 . 40 1024 - 1029 . DOI: 10.1117/1.1369411 http://doi.org/10.1117/1.1369411 .

Tritto, I.; Boggioni, L.; Ferro, D. R. . , Metallocene catalyzed ethene- and propene co -norbornene polymerization: mechanisms from a detailed microstructural analysis . Coord. Chem. Rev. , 2006 . 250 212 - 241 . DOI: 10.1016/j.ccr.2005.06.019 http://doi.org/10.1016/j.ccr.2005.06.019 .

Li, X.; Hou, Z. . Organometallic catalysts for copolymerization of cyclic olefins . Coord. Chem. Rev. , 2008 . 252 1842 - 1869 . DOI: 10.1016/j.ccr.2007.11.027 http://doi.org/10.1016/j.ccr.2007.11.027 .

Ban, H. T.; Hagihara, H.; Nishii, K.; Tsunogae, Y.; Nojima, S.; Shiono, T. . A new approach for controlling birefringent property of cyclic olefin copolymers . J. Polym. Sci., Part A: Polym. Chem. , 2008 . 46 7395 - 7400 . DOI: 10.1002/pola.23044 http://doi.org/10.1002/pola.23044 .

Ban, H. T.; Hagihara, H.; Tsunogae, Y.; Cai, Z. G.; Shiono, T. . Highly thermostable and low birefringent norbornene-styrene copolymers with advanced optical properties: a potential plastic substrate for flexible displays . J. Polym. Sci., Part A: Polym. Chem. , 2010 . 49 65 - 71 . DOI: 10.1002/pola.24416 http://doi.org/10.1002/pola.24416 .

Peruch, F.; Cramail, H.; Deffieux, A. . Homopolymerization and copolymerization of styrene and norbornene with Ni-based/MAO catalysts . Macromol. Chem. Phys. , 1998 . 199 2221 - 2227 . DOI: 10.1002/(SICI)1521-3935(19981001)199:10<2221::AID-MACP2221>3.0.CO;2-X http://doi.org/10.1002/(SICI)1521-3935(19981001)199:10<2221::AID-MACP2221>3.0.CO;2-X .

Zhao, C. T.; Ribeiro, M. R.; Portela, M. F.; Pereira, S.; Nunes, T. . Homo- and copolymerisation of norbornene and styrene with nickel bis(acetyl acetonate)/methylaluminoxane system . Eur. Polym. J. , 2001 . 37 45 - 54 . DOI: 10.1016/S0014-3057(00)00078-1 http://doi.org/10.1016/S0014-3057(00)00078-1 .

Suzuki, H.; Matsumura, S. I.; Satoh, Y.; Sogoh, K.; Yasuda, H. . Random copolymerizations of norbornene with other monomers catalyzed by novel Ni compounds involving N- or O-donated ligands . React. Funct. Polym. , 2004 . 58 77 - 91 . DOI: 10.1016/j.reactfunctpolym.2003.11.007 http://doi.org/10.1016/j.reactfunctpolym.2003.11.007 .

Bao, F.; Lv, X. Q.; Chen, Y. . Copolymerization of norbornene and styrene catalyzed by a series of bis( β -ketoamine) nickel(II) complexes in the presence of methylaluminoxane . Polym. Bull. , 2007 . 58 495 - 502 . DOI: 10.1007/s00289-006-0687-z http://doi.org/10.1007/s00289-006-0687-z .

Ogata, K.; Nishimura, N.; Yunokuchi, T.; Toyota, A. . Copolymerization of tetracyclododecene or norbornene with styrene in the presence of Ni(II) complex/MAO catalytic system: first example for transition metal catalyzed copolymerization of tetracyclododecene with styrene . J. Appl. Polym. Sci. , 2008 . 108 1562 - 565 . DOI: 10.1002/app.27826 http://doi.org/10.1002/app.27826 .

Li, Y.; Wu, Q.; Shan, M.; Gao, M. . Copolymerization of styrene and norbornene with β -diketiminato nickel/methylaluminoxane catalytic system . Appl. Organometal. Chem. , 2012 . 26 225 - 229 . DOI: 10.1002/aoc.2843 http://doi.org/10.1002/aoc.2843 .

Gao, H.; Chen, Y.; Zhu, F. M.; Wu, Q. . Copolymerization of norbornene and styrene catalyzed by a novel anilido-imino nickel complex/methylaluminoxane system . J. Polym. Sci., Part A: Polym. Chem. , 2006 . 44 5237 - 5246 . DOI: 10.1002/pola.21651 http://doi.org/10.1002/pola.21651 .

Xing, Y.; Chen, Y.; He, X. . Copolymerization of norbornene with styrene catalyzed by Ni{CF 3 C(O)CHC[N(naphthyl)]CH 3 } 2 /B(C 6 F 5 ) 3 and transparent films . J. Polym. Eng. , 2012 . 32 7 - 12 . .

Mi, X.; Ma, Z.; Wang, L.; Ke, Y.; Hu, Y. . Homo- and copolymerization of norbornene and styrene with Pd- and Ni-based novel bridged dinuclear diimine complexes and MAO . Macromol. Chem. Phys. , 2003 . 204 868 - 876 . DOI: 10.1002/macp.200390057 http://doi.org/10.1002/macp.200390057 .

Bao, F.; Ma, R.; Jiao, Y. H. . Homo- and copolymerization of norbornene with styrene catalyzed by a series of copper(II) complexes in the presence of methylaluminoxane . Appl. Organometal. Chem. , 2006 . 20 368 - 374 . DOI: 10.1002/aoc.1063 http://doi.org/10.1002/aoc.1063 .

Feng, Q.; Chen, D.; Feng, D.; Jiao, L.; Peng, Z.; Pei, L . Synthesis of poly(norbornene- co -styrene) copolymers containing high styrene incorporation using bis( β -ketoamino) copper catalysts . J. Polym. Res. , 2014 . 21 497 DOI: 10.1007/s10965-014-0497-1 http://doi.org/10.1007/s10965-014-0497-1 .

Franssen, N. M. G.; Reek, J. N. H.; de Bruin, B. . Synthesis of functional ‘polyolefins’: state of the art and remaining challenges . Chem. Soc. Rev. , 2013 . 42 5809 - 5832 . DOI: 10.1039/c3cs60032g http://doi.org/10.1039/c3cs60032g .

Nakamura, A.; Anselment, T. M. J.; Claverie, J.; Goodall, B.; Jordan, R. F.; Mecking, S.; Rieger, B.; Sen, A.; van Leeuwen, P. W. N. M.; Nozaki, K. . Ortho -phosphinobenzenesulfonate: a superb ligand for palladium-catalyzed coordination-insertion copolymerization of polar vinyl monomers . Acc. Chem. Res. , 2013 . 46 1438 - 1449 . DOI: 10.1021/ar300256h http://doi.org/10.1021/ar300256h .

Tan, C.; Chen, C. . Emerging palladium and nickel catalysts for copolymerization of olefins with polar monomers . Angew. Chem. Int. Ed. , 2019 . 58 7192 - 7200 . DOI: 10.1002/anie.201814634 http://doi.org/10.1002/anie.201814634 .

Liang, T.; Goudari, S.; Chen, C. L. . A simple and versatile nickel platform for the generation of branched high molecular weight polyolefins . Nat. Commun. , 2020 . 11 372 DOI: 10.1038/s41467-019-14211-0 http://doi.org/10.1038/s41467-019-14211-0 .

Chen, M.; Chen, C. . Direct and tandem routes for the copolymerization of ethylene with polar functionalized internal olefins . Angew. Chem. Int. Ed. , 2020 . 59 1206 - 1210 . DOI: 10.1002/anie.201913088 http://doi.org/10.1002/anie.201913088 .

Zou, C.; Chen, C. . Polar-functionalized, crosslinkable, self-healing and photoresponsive polyolefins . Angew. Chem. Int. Ed. , 2020 . 59 395 - 402 . DOI: 10.1002/anie.201910002 http://doi.org/10.1002/anie.201910002 .

Tan, C.; Qasim, M.; Pang, W. M.; Chen, C. . Ligand-metal secondary interaction in phosphine-sulfonate palladium and nickel catalyzed ethylene (co)polymerization . Polym. Chem. , 2020 . 11 411 - 416 . DOI: 10.1039/C9PY00904C http://doi.org/10.1039/C9PY00904C .

Wang, B.; Daugulis, O.; Brookhart, M. . Ethylene polymerization with Ni(II) diimine complexes generated from 8-halo-1-naphthylamines: the role of equilibrating syn/anti diastereomers in determining polymer properties . Organometallics , 2019 . 38 4658 - 4668 . DOI: 10.1021/acs.organomet.9b00649 http://doi.org/10.1021/acs.organomet.9b00649 .

Wang, F. Z.; Tian, S. S.; Lia, R. P.; Li, W. M.; Chen, C. . Ligand steric effects on naphthyl- α -diimine nickel catalyzed α -olefin polymerization . Chinese J. Polym. Sci. , 2018 . 36 157 - 162 . DOI: 10.1007/s10118-018-2038-6 http://doi.org/10.1007/s10118-018-2038-6 .

Tan, C.; Pang, W.; Chen, C. . A phenol-containing α -diimine ligand for nickel- and palladium-catalyzed ethylene polymerization . Chinese J. Polym. Sci. , 2019 . 37 974 - 980 . DOI: 10.1007/s10118-019-2232-1 http://doi.org/10.1007/s10118-019-2232-1 .

Sun, W.; Song, S.; Li, B.; Redshaw, C.; Hao, X.; Li, Y.; Wang, F. S . Ethylene polymerization by 2-iminopyridylnickel halide complexes: synthesis, characterization and catalytic influence of the benzhydryl group . Dalton Trans. , 2012 . 41 11999 - 12010 . .

Dai, S.; Sui, X.; Chen, C. . 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 .

Sun, Z.; Yue, E.; Qu, M.; Oleynik, I. V.; Oleynik, I. I.; Li, K.; Liang, T.; Zhang, W.; Sun, W. . 8-(2-Cycloalkylphenylimino)-5,6,7-trihydro-quinolylnickel halides: polymerizing ethylene to highly branched and lower molecular weight polyethylenes . Inorg. Chem. Front. , 2015 . 2 223 - 227 . DOI: 10.1039/C4QI00162A http://doi.org/10.1039/C4QI00162A .

Wang, Z.; Liu, Q.; Solan, G. A.; Sun, W. . Recent advances in Ni-mediated ethylene chain growth: N imine -donor ligand effects on catalytic activity, thermal stability and olig-/polymer structure . Coord. Chem. Rev. , 2017 . 350 68 - 83 . DOI: 10.1016/j.ccr.2017.06.003 http://doi.org/10.1016/j.ccr.2017.06.003 .

Nomura, K.; Bahuleyan, B. K.; Zhang, S.; Sharma, P. M. V.; Katao, S.; Igarashi, A.; Inagaki, A.; Tamm, M. . Synthesis and structural analysis of (imido)vanadium(V) dichloride complexes containing imidazolin-2-iminato- and imidazolidin-2-iminato ligands, and their use as catalyst precursors for ethylene (co)polymerization . Inorg. Chem. , 2014 . 53 607 - 623 . DOI: 10.1021/ic402747d http://doi.org/10.1021/ic402747d .

Nomura, K.; Fukuda, H.; Katao, S.; Fujiki, M.; Kim, H. J.; Kim, D. H.; Zhang, S. . Effect of ligand substituents in olefin polymerisation by half-sandwich titanium complexes containing monoanionic iminoimidazolidide ligands-MAO catalyst systems . Dalton Trans. , 2011 . 40 7842 - 7849 . DOI: 10.1039/c1dt10467e http://doi.org/10.1039/c1dt10467e .

Nomura, K.; Fukuda, H.; Matsuda, H.; Katao, S.; Patamma, S. . Synthesis and structural analysis of half-titanocenes containing 1,3-imidazolidin-2-iminato ligands: effect of ligand substituents in ethylene (co)polymerization . J. Org. Chem. , 2015 . 798 375 - 383 . DOI: 10.1016/j.jorganchem.2015.04.028 http://doi.org/10.1016/j.jorganchem.2015.04.028 .

Shoken, D; Shimon, L. J. W.; Tamm, M.; Eisen, M. S . Synthesis of imidazolin-2-iminato titanium complexes containing aryloxo ligands and their catalytic performance in the polymerization of α -olefins . Organometallics , 2016 . 35 1125 - 1131 . DOI: 10.1021/acs.organomet.6b00117 http://doi.org/10.1021/acs.organomet.6b00117 .

Shoken, D.; Sharma, M.; Botoshansky, M.; Tamm, M.; Eisen, M. S. . Mono(imidazolin-2-iminato) titanium complexes for ethylene polymerization at low amounts of methylaluminoxane . J. Am. Chem. Soc. , 2013 . 135 12592 - 12595 . DOI: 10.1021/ja406925z http://doi.org/10.1021/ja406925z .

Nomura, K.; Patamma, S.; Matsuda, H.; Katao, S.; Tsutsumi, K.; Fukuda, H. . Synthesis of half-titanocenes containing 1,3-imidazolidin-2-iminato ligands of type, Cp*TiCl 2 [1,3-R 2 (CH 2 N) 2 C]N] : highly active catalyst precursors in ethylene (co)polymerization . RSC Adv. , 2015 . 5 64503 - 64513 . DOI: 10.1039/C5RA11402K http://doi.org/10.1039/C5RA11402K .

Haas, I.; Hubner, C.; Kretschmer, W. P.; Kempe, R. . A highly efficient titanium catalyst for the synthesis of ultrahigh-molecular-weight polyethylene (UHMWPE) . Chem. Eur. J. , 2013 . 19 9132 - 9136 . DOI: 10.1002/chem.201301176 http://doi.org/10.1002/chem.201301176 .

Neuba, A.; Haase, R.; Bernard, M.; Flörke, U.; Herres-Pawlis, S. . A systematic study on the coordination properties of the guanidine ligand N 1 ,N 2 -bis(1,3-dimethylimidazolidin-2-ylidene)-ethane-1,2-diamine with the metals Mn, Co, Ni, Ag and Cu . Z. Anorg. Allg. Chem. , 2008 . 634 2511 - 2517 . DOI: 10.1002/zaac.200800335 http://doi.org/10.1002/zaac.200800335 .

Filimon, S. A.; Hrib, C. G.; Randoll, S.; Neda, I.; Jones, P. G.; Tamm, M. . Quinine-derived imidazolidin-2-imine ligands: synthesis, coordination chemistry, and application in catalytic transfer hydrogenation . Z. Anorg. Allg. Chem. , 2010 . 636 691 - 699 . DOI: 10.1002/zaac.200900485 http://doi.org/10.1002/zaac.200900485 .

Li, M.; Shu, X.; Cai, Z.; Eisen, M. S. . Synthesis, structures, and norbornene polymerization behavior of neutral nickel(II) and palladium(II) complexes bearing aryloxide imidazolidin-2-imine ligands . Organometallics , 2018 . 37 1172 - 1180 . DOI: 10.1021/acs.organomet.8b00059 http://doi.org/10.1021/acs.organomet.8b00059 .

Li, M.; Cai, Z.; Eisen, M. S. . Neutral nickel(II) complexes bearing aryloxide imidazolin-2-imine ligands for efficient copolymerization of norbornene and polar monomers . Organometallics , 2018 . 37 4753 - 4762 . DOI: 10.1021/acs.organomet.8b00752 http://doi.org/10.1021/acs.organomet.8b00752 .

Rösener, T.; Hoffmann, A.; Herres-Pawlis, S. . Next generation of guanidine quinoline copper complexes for highly controlled ATRP: Influence of backbone substitution on redox chemistry and solubility . Eur. J. Inorg. Chem. , 2018 . 3164 - 3175 . .

Stanek, J.; Konrad, M.; Mannsperger, J.; Hoffmann, A.; Herres-Pawlis, S. . Influence of functionalized substituents on the electron transfer abilities of copper guanidinoquinoline complexes . Eur. J. Inorg. Chem. , 2018 . 4997 - 5006 . .

Ferretti, F.; Gallo, E.; Ragaini, F. . Nitrogen ligands effects in the palladium-catalyzed carbonylation reaction of nitrobenzene to give N-methyl phenylcarbamate . J. Organomet. Chem. , 2014 . 771 59 - 67 . DOI: 10.1016/j.jorganchem.2014.04.010 http://doi.org/10.1016/j.jorganchem.2014.04.010 .

Tang, P.; Wang, W.; Ritter, T. . Deoxyfluorination of phenol . J. Am. Chem. Soc. , 2011 . 133 11482 - 11484 . DOI: 10.1021/ja2048072 http://doi.org/10.1021/ja2048072 .

Schrempp, D. F.; Leingang, S.; Schnurr, M.; Kaifer, E.; Wadepohl, H.; Himmel, H. J. . Inter- and intramolecular electron transfer in copper complexes: electronic entatic state with redox-active guanidine ligands . Chem. Eur. J. , 2017 . 23 13607 - 13611 . DOI: 10.1002/chem.201703611 http://doi.org/10.1002/chem.201703611 .

Guazzelli, L.; Chiappe, C. . Investigation of a family of structurally-related guanidinium ionic liquids through XPS and thermal analysis . J. Mol. Liq. , 2019 . 277 280 - 289 . DOI: 10.1016/j.molliq.2018.12.083 http://doi.org/10.1016/j.molliq.2018.12.083 .

Antonov, A. A.; Semikolenova, N. V.; Talsi, E. P.; Matsko, M.A.; Zakharov, V. A.; Bryliakov, K. P. . 2-Iminopyridine nickel(II) complexes bearing electron-withdrawing groups in the ligand core: synthesis, characterization, ethylene oligo- and polymerization behavior . J. Organomet. Chem. , 2016 . 822 241 - 249 . DOI: 10.1016/j.jorganchem.2016.08.031 http://doi.org/10.1016/j.jorganchem.2016.08.031 .

Lovett, D. M.; Thierer, L. M.; Santos, E. E. P.; Hardie, R. L.; Dougherty, W. G.; Piro, N. A.; Kassel, W. S.; Cromer, B. M.; Coughlin, E. B.; Zubris, D. L. . Structural analysis of imino- and amino-pyridine ligands for Ni(II): precatalysts for the polymerization of ethylene . J. Organomet. Chem. , 2018 . 863 44 - 53 . DOI: 10.1016/j.jorganchem.2018.03.012 http://doi.org/10.1016/j.jorganchem.2018.03.012 .

Zhang, R.; Wang, Z.; Flisak, Z.; Hao, X.; Liu, Q.; Sun, W. . Achieving branched polyethylene waxes by aryliminocycloocta[ b ]pyridylnickel precatalysts: synthesis, characterization, and ethylene polymerization . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 2601 - 2610 . DOI: 10.1002/pola.28653 http://doi.org/10.1002/pola.28653 .

Song, D.; Shi, X.; Wang, Y.; Yang, J.; Li, Y. . Ligand steric and electronic effects on β -ketiminato neutral nickel(ii) olefin polymerization catalysts . Organometallics , 2012 . 31 966 - 975 . DOI: 10.1021/om2010194 http://doi.org/10.1021/om2010194 .

Kausar, A. . Novel nanofiltration membranes of poly(4-chlorostyrene)-grafted-1-(4-thiocarbamoylaminophenyl-sulfonylphenyl)thiourea and gold/polystyrene composite nanoparticle . Am. J. Polym. Sci. Eng. , 2014 . 2 33 - 49 . .

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Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene

DOI：10.1007/s10118-020-2400-3

摘要

Abstract

关键词

Keywords

references