Investigating the Effects of <italic style="font-style: italic">Para</italic>-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts

Yi Yan; Shi-Fang Yuan; Ming Liu; Gregory A. Solan; Yan-Ping Ma; Tong-Ling Liang; Wen-Hua Sun

doi:10.1007/s10118-022-2670-z

Your Location：

Home >

Browse articles >

Investigating the Effects of Para-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts

RESEARCH ARTICLE | Updated：2022-03-23

- Investigating the Effects of Para-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts
- Chinese Journal of Polymer Science Vol. 40, Issue 3, Pages: 266-279(2022)
- Affiliations：
  
  a.Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China
  b.Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Sciences, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, China
  c.Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK
  d.State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
- Author bio：
  
  yuansf@sxu.edu.cn (S.F.Y.)
  gas8@leicester.ac.uk (G.A.S.)
  whsun@iccas.ac.cn (W.H.S.)
- Funds：
- DOI：10.1007/s10118-022-2670-z
  CLC：
- Received：25 October 2021，
  
  Revised：2021-11-22，
  
  Accepted：23 November 2021，
  
  Online First：11 January 2022，
  
  Published：01 March 2022
- Accepted：
Scan QR Code
Yan, Y.; Yuan, S. F.; Liu, M.; Solan, G. A.; Ma, Y. P.; Liang, T. L.; Sun, W. H. Investigating the effects of para-methoxy substitution in sterically enhanced unsymmetrical bis(arylimino)pyridine-cobalt ethylene polymerization catalysts. Chinese J. Polym. Sci. 2022, 40, 266–279

Yi Yan, Shi-Fang Yuan, Ming Liu, et al. Investigating the Effects of Para-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts[J]. Chinese Journal of Polymer Science, 2022, 40(3): 266-279. DOI: 10.1007/s10118-022-2670-z.
Yan, Y.; Yuan, S. F.; Liu, M.; Solan, G. A.; Ma, Y. P.; Liang, T. L.; Sun, W. H. Investigating the effects of para-methoxy substitution in sterically enhanced unsymmetrical bis(arylimino)pyridine-cobalt ethylene polymerization catalysts. Chinese J. Polym. Sci. 2022, 40, 266–279 DOI： 10.1007/s10118-022-2670-z.

Yi Yan, Shi-Fang Yuan, Ming Liu, et al. Investigating the Effects of Para-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts[J]. Chinese Journal of Polymer Science, 2022, 40(3): 266-279. DOI: 10.1007/s10118-022-2670-z. DOI：

摘要

Abstract

A group of five bis(arylimino)pyridine-cobalt(II) chloride complexes

[2-{(2

6-(Ph

CH)

-4-MeOC

)N＝CMe}-6-(ArN＝CMe)C

N]CoCl

(Ar = 2

6-Me

Co1

6-Et

Co2

6-iPr

Co3

6-Me

Co4

6-Et

-4-MeC

Co5

)

each containing one

-4-methoxy-2

6-dibenzhydrylphenyl group and one smaller sterically/electronically variable

-aryl group

have been synthesized in good yield (

71%) from the corresponding neutral terdentate nitrogen-donor precursor

–

. All complexes have been characterized by

H-NMR and FTIR spectroscopy with the former highlighting the paramagnetic nature of these cobaltous species and the unsymmetrical nature of the chelating ligand. The molecular structures of

Co3

and

Co4

emphasize the steric differences of the two inequivalent

-aryl groups and the distorted square pyramidal geometry about the metal centers. In the presence of MAO or MMAO

Co1

–

Co5

collectively displayed high activities for ethylene polymerization producing high molecular weight polyethylenes that

in general

exhibited narrow dispersities (

values: 2.12–4.07). Notably

the least sterically hindered

Co1

when activated with MAO was the most productive (6.92×10

·mol

−1

(Co)

·h

−1

) at an operating temperature of 60 ºC. Conversely

the most sterically hindered

Co3

/MMAO produced the highest molecular weight polyethylene (

=6.29×10

g·mol

−1

). All the polymers displayed high linearity as demonstrated by their melting temperatures (

130 °C) and their

H- and

C-NMR spectra. By comparison of

Co1

with its

para

-methyl

-chloro and -nitro counterparts

the presence of the

para

-methoxy substituent showed the most noticeable effect of enhancing the thermal stability of the catalyst.

关键词

Keywords

references

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 , 6414-6415.

Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M . Living polymerization of α -olefins using Ni(II)- α -diimine catalysts. synthesis of new block polymers based on α -olefins . J. Am. Chem. Soc. , 1996 . 118 11664 - 11665 . DOI: 10.1021/ja962516h http://doi.org/10.1021/ja962516h .

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

Britovsek, G. P. J.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White A. J. P.; Williams. D. J . Novel olefin polymerization catalysts based on iron and cobalt . Chem. Commun. , 1998 . 7 849 - 850 . .

Britovsek, G. J. P.; Bruce, M.; Gibson,V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Strӧmberg, S. White, A. J. P. Williams, D. J . Iron and cobalt ethylene polymerization catalysts bearing 2,6-bis(imino)pyridyl ligands: synthesis, structures, and polymerization studies . J. Am. Chem. Soc. , 1999 . 121 8728 - 8740 . DOI: 10.1021/ja990449w http://doi.org/10.1021/ja990449w .

Harth, E. M.; Hecht, S.; Helms, B.; Malmstrom, E. E.; Fréchet, J. M. J.; Hawker, C. J . The effect of macromolecular architecture in nanomaterials: a comparison of site isolation in porphyrin core dendrimers and their isomeric linear analogues . J. Am. Chem. Soc. , 2002 . 124 3926 - 3938 . DOI: 10.1021/ja025536u http://doi.org/10.1021/ja025536u .

Gibson, V. C.; Redshaw, C.; Solan, G. A . Bis(imino)pyridines: surprisingly reactive ligands and a gateway to new families of catalysts . Chem. Rev. , 2007 . 107 1745 - 1776 . DOI: 10.1021/cr068437y http://doi.org/10.1021/cr068437y .

Gibson, V. C.; Solan, G. A . Iron-based and cobalt-based olefin polymerisation catalysts . Top. Organomet. Chem. , 2009 . 26 107 - 158 . .

Gibson, V. C.; Solan, G. A . Olefin oligomerizations and polymerizations catalyzed by iron and cobalt complexes bearing bis(imino)pyridine ligands . Wiley-VCH, Weinheim , 2010 . 5 111 - 141 . .

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

Ma, J.; Feng, C.; Wang, S. L.; Zhao, K. Q.; Sun, W. H.; Redshaw, C.; Solan, G. A . Bi- and tri-dentate imino-based iron and cobalt pre-catalysts for ethylene oligo-/polymerization . Inorg. Chem. Front. , 2014 . 1 14 - 34 . DOI: 10.1039/C3QI00028A http://doi.org/10.1039/C3QI00028A .

Flisak, Z.; Sun, W. H . Progression of diiminopyridines: from single application to catalytic versatility . ACS Catal. , 2015 . 5 4713 - 4724 . DOI: 10.1021/acscatal.5b00820 http://doi.org/10.1021/acscatal.5b00820 .

Small, B. L . Discovery and development of pyridine-bis(imine) and related catalysts for olefin polymerization and oligomerization . Acc. Chem. Res. , 2015 . 48 2599 - 2611 . DOI: 10.1021/acs.accounts.5b00252 http://doi.org/10.1021/acs.accounts.5b00252 .

Wang, Z.; Liu, Q.; Solan, G. A.; Sun, W. H . Recent advances in Ni-mediated ethylene chain growth: Nimine-donor ligand effects on catalytic activity, thermal stability and oligo-/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 .

Wang, Z.; Solan, G. A.; Zhang, W. J.; Sun, W. H . Carbocyclic-fused N,N,N -pincer ligands as ring-strain adjustable supports for iron and cobalt catalysts in ethylene oligo-/polymerization . Coord. Chem. Rev. , 2018 . 363 92 - 108 . DOI: 10.1016/j.ccr.2018.02.016 http://doi.org/10.1016/j.ccr.2018.02.016 .

Bariashir, C.; Huang, C.; Solan, G. A.; Sun, W. H . Recent advances in homogeneous chromium catalyst design for ethylene tri-, tetra-, oligo- and polymerization . Coord. Chem. Rev. , 2019 . 385 208 - 229 . DOI: 10.1016/j.ccr.2019.01.019 http://doi.org/10.1016/j.ccr.2019.01.019 .

Mitchell, N. E.; Long, B. K . Recent advances in thermally robust, late transition metal-catalyzed olefin polymerization . Polym. Int. , 2019 . 68 14 - 26 . DOI: 10.1002/pi.5694 http://doi.org/10.1002/pi.5694 .

Yuan, S. F.; Yan, Y.; Solan, G. A.; Ma, Y.; Sun, W. H . Recent advancements in N-ligated group 4 molecular catalysts for the (co)polymerization of ethylene . Coord. Chem. Rev. , 2020 . 411 213254 DOI: 10.1016/j.ccr.2020.213254 http://doi.org/10.1016/j.ccr.2020.213254 .

Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Mastroianni, S.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J . Bis(imino)pyridyl iron and cobalt complexes: the effect of nitrogen substituents on ethylene oligomerisation and polymerization . J. Chem. Soc. Dalton Trans. , 2001 . 1639 - 1644 . .

McTavish, S.; Britovsek, G. J. P.; Smit, T. M.; Gibson, V. C.; White, A. J. P.; Williams, D. J . Iron-based ethylene polymerization catalysts supported by bis(imino)pyridine ligands: derivatization via deprotonation/alkylation at the ketimine methyl position . J. Mol. Catal. A: Chem. , 2007 . 261 293 - 300 . DOI: 10.1016/j.molcata.2006.10.028 http://doi.org/10.1016/j.molcata.2006.10.028 .

Smit, T. M.; Tomov, A. K.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J . The effect of imine-carbon substituents in bis(imino)pyridine-based ethylene polymerisation catalysts across the transition series . Catal. Sci. Technol. , 2012 . 2 643 - 655 . DOI: 10.1039/c2cy00448h http://doi.org/10.1039/c2cy00448h .

Zhang, W.; Sun, W. H.; Redshaw, C . Tailoring iron complexes for ethylene oligomerization and/or polymerization . Dalton Trans. , 2013 . 42 8988 - 8997 . DOI: 10.1039/C2DT32337K http://doi.org/10.1039/C2DT32337K .

Yue, E.; Zeng, Y.; Zhang, W.; Sun, Y.; Cao, X. P.; Sun, W. H . Highly linear polyethylenes using the 2-(1-(2,4-dibenzhydrylnaphthylimino)ethyl)-6-(1-(arylimino)ethyl)-pyridylcobalt chlorides: synthesis, characterization and ethylene polymerization . Sci. China Chem. , 2016 . 59 1291 - 1300 . DOI: 10.1007/s11426-016-0157-0 http://doi.org/10.1007/s11426-016-0157-0 .

Yang, W.; Yi, J.; Ma, Z.; Sun, W. H . 2D-QSAR modeling on the catalytic activities of 2-azacyclyl-6- aryliminopyridylmetal precatalysts in ethylene oligomerization . Cat. Commun. , 2017 . 101 40 - 43 . DOI: 10.1016/j.catcom.2017.07.018 http://doi.org/10.1016/j.catcom.2017.07.018 .

Bariashir, C.; Wang, Z.; Du, S.; Solan, G. A.; Huang, C.; Liang, T.; Sun, W. H . Cycloheptyl-fused NNO-ligands as electronically modifiable supports for M(II) (M=Co,Fe) chloride precatalysts; probing performance in ethylene oligo-/polymerization . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 3980 - 3989 . DOI: 10.1002/pola.28767 http://doi.org/10.1002/pola.28767 .

Zhang, S.; Sun, W . H.; Xiao, T.; Hao, X. Ferrous and cobaltous chlorides bearing 2,8-bis(imino)quinolines: highly active catalysts for ethylene polymerization at high temperature . Organometallics , 2010 . 29 1168 - 1173 . DOI: 10.1021/om9010142 http://doi.org/10.1021/om9010142 .

Sun, W.-H.; Hao, P.; Li, G.; Zhang, S.; Wang, W.; Yi, J . Synthesis and characterization of iron and cobalt dichloride bearing 2-quinoxalinyl-6-iminopyridines and their catalytic behavior toward ethylene reactivity . J. Organomet. Chem. , 2007 . 692 4506 - 4518 . DOI: 10.1016/j.jorganchem.2007.04.027 http://doi.org/10.1016/j.jorganchem.2007.04.027 .

Wang, K.; Wedeking, K.; Zuo, W.; Zhang, D.; Sun, W. H . Iron(II) and cobalt(II) complexes bearing N -((pyridin-2-yl)methylene)-quinolin-8-amine derivatives: Synthesis and application to ethylene oligomerization . J. Organomet. Chem. , 2008 . 693 1073 - 1080 . DOI: 10.1016/j.jorganchem.2007.12.030 http://doi.org/10.1016/j.jorganchem.2007.12.030 .

Wang, L.; Sun, W. H.; Han, L.; Yang, H.; Hu, Y.; Jin, X . Late transition metal complexes bearing 2,9-bis(imino)-1,10-phenanthrolinyl ligands: synthesis, characterization and their ethylene activity . J. Organomet. Chem. , 2002 . 658 62 - 70 . DOI: 10.1016/S0022-328X(02)01623-6 http://doi.org/10.1016/S0022-328X(02)01623-6 .

Sun, W. H.; Jie, S.; Zhang, S.; Zhang, W.; Song, Y.; Ma, H . Iron complexes bearing 2-imino-1,10-phenanthrolinyl ligands as highly active catalysts for ethylene oligomerization . Organometallics , 2006 . 25 666 - 677 . DOI: 10.1021/om050891p http://doi.org/10.1021/om050891p .

Pelletier, J. D. A.; Champouret, Y. D. M.; Cardarso, J.; Clowes, L.; Gañete, M.; Singh, K.; Thanarajasingham, V.; Solan, G. A . Electronically variable imino-phenanthrolinyl-cobalt complexes; synthesis, structures and ethylene oligomerisation studies . J. Organomet. Chem. , 2006 . 691 4114 - 4123 . DOI: 10.1016/j.jorganchem.2006.06.018 http://doi.org/10.1016/j.jorganchem.2006.06.018 .

Jie, S.; Zhang, S.; Wedeking, K.; Zhang, W.; Ma, H.; Lu, X.; Deng, Y.; Sun, W. H . Cobalt(II) complexes bearing 2-imino-1,10-phenanthroline ligands: synthesis, characterization and ethylene oligomerization . C. R. Chim. , 2006 . 9 1500 - 1509 . DOI: 10.1016/j.crci.2006.09.007 http://doi.org/10.1016/j.crci.2006.09.007 .

Jie, S.; Zhang, S.; Sun, W . H.; Kuang, X.; Liu, T.; Guo, J. Iron(II) complexes ligated by 2-imino-1,10-phenanthrolines: Preparation and catalytic behavior toward ethylene oligomerization . J. Mol. Catal. A: Chem. , 2007 . 269 85 - 96 . DOI: 10.1016/j.molcata.2007.01.008 http://doi.org/10.1016/j.molcata.2007.01.008 .

Jie, S.; Zhang, S.; Sun, W. H . 2-Arylimino-9-phenyl-1,10-phenanthrolinyl-iron, -cobalt and -nickel complexes: synthesis, characterization and ethylene oligomerization behavior . Eur. J. Inorg. Chem. , 2007 . 2007 5584 - 5598 . .

Sun, W. H.; Hao, P.; Zhang, S.; Shi, Q.; Zuo, W.; Tang, X . Iron(II) and cobalt(II) 2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl complexes as catalysts for ethylene oligomerization and polymerization . Organometallics , 2007 . 26 2720 - 2734 . DOI: 10.1021/om0700819 http://doi.org/10.1021/om0700819 .

Chen, Y.; Hao, P.; Zuo, W.; Gao, K.; Sun, W. H . 2-(1-Isopropyl-2-benzimidazolyl)-6-(1-aryliminoethyl)- pyridyl transition metal (Fe, Co, and Ni) dichlorides: Syntheses, characterizations and their catalytic behaviors toward ethylene reactivity . J. Organomet. Chem. , 2008 . 693 1829 - 1840 . DOI: 10.1016/j.jorganchem.2008.02.007 http://doi.org/10.1016/j.jorganchem.2008.02.007 .

Gao, R.; Li, Y.; Wang, F.; Sun, W. H.; Bochmann, M . 2-Benzoxazolyl-6-[1-(arylimino)ethyl]- pyridyliron(II) chlorides as ethylene oligomerization catalysts . Eur. J. Inorg. Chem. , 2009 . 691 4149 - 4156 . .

Xiao, L.; Gao, R.; Zhang, M.; Li, Y.; Cao, X.; Sun, W. H . 2-(1 H -2-benzimidazolyl)-6- (1-(arylimino)ethyl)pyridyl iron(ii) and cobalt(ii) dichlorides: syntheses, characterizations, and catalytic behaviors toward ethylene reactivity . Organometallics , 2009 . 28 2225 - 2233 . DOI: 10.1021/om801141n http://doi.org/10.1021/om801141n .

Yu, J.; Huang, W.; Wang, L.; Redshaw, C.; Sun, W. H . 2-[1-(2,6-Dibenzhydryl-4-methylphenylimino)- ethyl]-6-[1-(arylimino)ethyl]- pyridylcobalt(II) dichlorides: synthesis, characterization and ethylene polymerization behavior . Dalton Trans. , 2011 . 40 10209 - 10214 . DOI: 10.1039/c1dt11062d http://doi.org/10.1039/c1dt11062d .

He, F.; Zhao, W.; Cao, X. P.; Liang, T.; Redshaw, C.; Sun, W. H . 2-[1-(2,6-Dibenzhydryl-4- chlorophenylimino)ethyl]-6-[1-aryliminoethyl]pyridyl cobalt dichlorides: synthesis, characterization and ethylene polymerization behavior . J. Organomet. Chem. , 2012 . 713 209 - 216 . DOI: 10.1016/j.jorganchem.2012.05.020 http://doi.org/10.1016/j.jorganchem.2012.05.020 .

Mahmood, Q.; Ma, Y.; Hao, X.; Sun, W. H . Substantially enhancing the catalytic performance of bis(imino)pyridylcobaltous chloride pre-catalysts adorned with benzhydryl and nitro groups for ethylene polymerization . Appl. Organomet. Chem. , 2019 . 33 e4857 .

Zhang, W.; Wang, S.; Du, S.; Guo, C. Y.; Hao, X.; Sun, W. H . 2-(1-(2,4-Bis((di(4-fluorophenyl)methyl)-6-methylphenylimino)ethyl)-6-(1-(arylimino)ethyl)pyridylmetal (iron or cobalt) complexes: synthesis, characterization and ethylene polymerization behavior . Macromol. Chem. Phys. , 2014 . 215 1797 - 1890 . DOI: 10.1002/macp.201400140 http://doi.org/10.1002/macp.201400140 .

Sun, W. H.; Zhao, W.; Yu, J.; Zhang, W.; Hao, X.; Redshaw, C . Enhancing the activity and thermal stability of iron precatalysts using 2-(1-{2,6-bis[bis(4-fluorophenyl)methyl]-4-methylphenylimino} ethyl)-6-[1-(arylimino)ethyl]pyridines . Macromol. Chem. Phys. , 2012 . 213 1266 - 1273 . DOI: 10.1002/macp.201200051 http://doi.org/10.1002/macp.201200051 .

Liu, T.; Ma, Y. P.; Solan, G. A.; Liang, T.; Sun, W. H . Exploring ortho -(4,4’-dimethoxybenzhydryl) substitution in iron ethylene polymerization catalysts: co-catalyst effects, thermal stability, and polymer molecular weight variations . Appl. Organomet. Chem. , 2021 . 35 e6259 .

Meiries, S.; Speck, K.; Cordes, D. B.; Slawin, A. M. Z.; Nolan, S. P . [Pd(IPr*OMe)(acac)Cl]: tuning the N -heterocyclic carbene in catalytic C−N bond formation . Organometallics , 2012 . 32 330 - 339 . .

Wu, R.; Wang, Y.; Zhang, R. N; Guo, C. Y.; Flisak, Z.; Sun, Y.; Sun. W. H . Finely tuned nickel complexes as highly active catalysts affording branched polyethylene of high molecular weight: 1-(2,6-dibenzhydryl-4-methoxyphenylimino)-2-(arylimino)acenaphthylenenickel halides . Polymer , 2018 . 153 574 - 586 . DOI: 10.1016/j.polymer.2018.08.056 http://doi.org/10.1016/j.polymer.2018.08.056 .

Wang, S.; Zhao, W.; Hao, X.; Li, B.; Redshaw, C.; Li, Y.; Sun, W.-H . 2-(1-{2,6-Bis[bis(4-fluorophenyl- methyl]-4-methylphenylimino}ethyl)-6-[1-(arylimino)ethyl]pyridylcobalt dichlorides: synthesis, characterization and ethylene polymerization behavior . J. Organomet. Chem. , 2013 . 731 78 - 84 . DOI: 10.1016/j.jorganchem.2013.02.016 http://doi.org/10.1016/j.jorganchem.2013.02.016 .

Lai, J.; Zhao, W.; Yang, W.; Redshaw, C.; Liang, T.; Liu, Y.; Sun, W. H . 2-[1-(2,4-Dibenzhydryl-6-methylphenylimino)ethyl]-6-[1-(arylimino)ethyl]pyridylcobalt(II) dichlorides: synthesis, characterization and ethylenepolymerization behavior . Polym. Chem. , 2012 . 3 787 - 793 . DOI: 10.1039/c2py00590e http://doi.org/10.1039/c2py00590e .

Du, S.; Kong, S.; Shi, Q.; Mao, J.; Guo, C.; Yi, J.; Liang, T.; Sun, W. H . Enhancing the activity and thermal stability of nickel complex precatalysts using 1-[2,6-bis(bis(4-fluorophenyl)-methyl)-4-methyl phenylimino]-2-aryliminoacenaphthylene derivatives . Organometallics , 2015 . 34 582 - 590 . DOI: 10.1021/om500943u http://doi.org/10.1021/om500943u .

Wang, S.; Li, B.; Liang, T.; Redshaw, C.; Li, Y.; Sun, W. H . Synthesis, characterization and catalytic behavior toward ethylene of 2-[1-(4,6-dimethyl-2-benzhydrylphenylimino)ethyl]-6-[1-(arylimino)- ethyl]- pyridylmetal (iron or cobalt) chlorides . Dalton Trans. , 2013 . 42 9188 - 9197 . DOI: 10.1039/c3dt00011g http://doi.org/10.1039/c3dt00011g .

Zhang, R.; Ma, Y.; Han, M.; Solan, G. A.; Pi, Y.; Sun, Y.; Sun, W. H . Exceptionally high molecular weight linear polyethylene by using N,N,N ′-Co catalysts appended with a N ′-2,6-bis{di(4-fluorophenyl) methyl}-4-nitrophenyl group . Appl. Organomet. Chem. , 2019 . 33 e5175 .

Du, S.; Zhang, W.; Yue, E.; Huang, F.; Liang, T.; Sun, W. H . α,α ′-Bis(arylimino)-2,3,5,6-bis- (pentamethylene)pyridylcobalt chlorides: synthesis, characterization and ethylene polymerization behavior . Eur. J. Inorg. Chem. , 2016 . 1748 - 1755 . .

Du, S.; Wang, X.; Zhang, W.; Flisak, Z.; Sun, Y.; Sun, W. H . A practical ethylene polymerization for vinyl-polyethylenes: synthesis, characterization and catalytic behavior of α,α ’-bisimino-2,3,5,6- bis(pentamethylene)pyridyliron chlorides . Polym. Chem. , 2016 . 7 4188 - 4197 . DOI: 10.1039/C6PY00745G http://doi.org/10.1039/C6PY00745G .

Han, M.; Zhang, Q.; Oleynik, I. I.; Suo, H.; Solan, G. A.; Oleynik, I.V.; Ma, Y.; Liang, T.; Sun, W. H . High molecular weight polyethylenes of narrow dispersity promoted using bis(arylimino) cyclohepta[ b ]pyridine-cobalt catalysts orthosubstituted with benzhydryl & cycloalkyl groups . Dalton Trans. , 2020 . 49 4774 - 4784 . DOI: 10.1039/D0DT00576B http://doi.org/10.1039/D0DT00576B .

Huang, F.; Zhang, W.; Sun, Y.; Hu, X.; Solan, G. A.; Sun, W. H . Thermally stable and highly active cobalt precatalysts for vinyl-polyethylenes with narrow polydispersities: integrating fused-ring and imino-carbon protection into ligand design . New J. Chem. , 2016 . 40 8012 - 8023 . DOI: 10.1039/C6NJ01867J http://doi.org/10.1039/C6NJ01867J .

Suo, H.; Oleynik, I. I.; Bariashir, C.; Oleynik, I.; Wang, Z.; Solan, G. A.; Ma, Y.; Liang, T.; Sun, W. H . Strictly linear polyethylene using co-catalysts chelated by fused bis(arylimino)pyridines: probing ortho -cycloalkyl ring-size effects on molecular weight . Polymer , 2018 . 149 45 - 54 . DOI: 10.1016/j.polymer.2018.06.066 http://doi.org/10.1016/j.polymer.2018.06.066 .

Guo, J.; Wang, Z.; Zhang, W.; Oleynik, I. I.; Vignesh, A.; Oleynik, I. V.; Hu, X.; Sun, Y.; Sun, W. H . Highly linear polyethylenes achieved using thermo-stable and efficient cobalt precatalysts bearing carbocyclic-fused N,N,N -pincer ligand . Molecules , 2019 . 24 1176 DOI: 10.3390/molecules24061176 http://doi.org/10.3390/molecules24061176 .

Bariashir, C.; Wang, Z.; Suo, H.; Zada, M.; Solan, G. A.; Ma, Y.; Liang, T.; Sun, W. H . Narrow dispersed linear polyethylene using cobalt catalysts bearing cycloheptyl-fused bis(imino)pyridines; probing the effects of ortho -benzhydryl substitution . Eur. Polym. J. , 2019 . 110 240 - 251 . DOI: 10.1016/j.eurpolymj.2018.11.010 http://doi.org/10.1016/j.eurpolymj.2018.11.010 .

Huang, Y.; Zhang, R.; Liang, T.; Hu, X.; Solan, G. A.; Sun, W. H . Selectivity effects on N,N,N ′-cobalt catalyzed ethylene dimerization/trimerization dictated through choice of aluminoxane cocatalyst . Organometallics , 2019 . 38 1143 - 1150 . DOI: 10.1021/acs.organomet.8b00924 http://doi.org/10.1021/acs.organomet.8b00924 .

Zada, M.; Vignesh, A.; Suo, H.; Ma, Y.; Liu, H.; Sun, W. H . N,N,N -type iron(II) complexes consisting sterically hindered dibenzocycloheptyl group: synthesis and catalytic activity towards ethylene polymerization . Mol. Catal. , 2020 . 492 110981 DOI: 10.1016/j.mcat.2020.110981 http://doi.org/10.1016/j.mcat.2020.110981 .

Han, M.; Zhang, Q.; Oleynik, I. I.; Suo, H.; Oleynik, I. V.; Solan, G. A.; Ma, Y.; Liang, T.; Sun, W. H . Adjusting ortho -cycloalkyl ring size in a cycloheptyl-fused N,N,N -iron catalyst as means to control catalytic activity and polyethylene properties . Catalysts , 2020 . 10 1002 DOI: 10.3390/catal10091002 http://doi.org/10.3390/catal10091002 .

Yuan, S. F.; Fan, Z.; Yan, Y.; Ma, Y.; Han M.; Liang, T.; and Sun, W. H . Achieving polydispersive HDPE by N,N,N -Co precatalysts appended with N -2,4-bis(di(4-methoxyphenyl)methyl)-6-methylphenyl . RSC Adv. , 2020 . 10 43400 - 43411 . DOI: 10.1039/D0RA09333E http://doi.org/10.1039/D0RA09333E .

Yuan, S. F.; Fan, Z.; Han M.; Yan, Y.; Flisak, Z.; Ma, Y.; Liang, T.; Sun, W. H . Enhancing performance of bis(arylimino)pyridine-iron precatalyst for ethylene polymerization by substitution with the 2,4-bis(4,4'-dimethoxybenzhydryl)-6-methylphenyl group . Eur. Polym. J. , 2021 . 16 1571 - 1580 . .

Guo, L.; Gao, H.; Zhang, L.; Zhu, F.; Wu, Q . 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 2118 - 2125 . DOI: 10.1021/om9010356 http://doi.org/10.1021/om9010356 .

Zhao, W.; Yue, E.; Wang, X.; Yang, W.; Chen, Y.; Hao, X.; Cao, X.; Sun, W. H . Activity and stability spontaneously enhanced toward ethylene polymerization by employing 2-(1-(2,4-dibenzhydryl- naphthylimino)ethyl)-6-(1-(arylimino)ethyl) pyridyliron(II) dichlorides . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 988 - 996 . DOI: 10.1002/pola.28459 http://doi.org/10.1002/pola.28459 .

Ionkin, A. S.; Marshall, W. J.; Adelman, D. J.; Fones, B. B.; Fish, B. M.; Schiauer, M. F . Modification of iron(II) tridentate bis(imino)pyridine complexes by a boryl group for the production of α -olefins at high temperature . Organometallics , 2008 . 27 1902 - 1911 . DOI: 10.1021/om800036b http://doi.org/10.1021/om800036b .

Zhang, R; Han, M.; Ma, Y.; Solan, G. A.; Liang, T.; Sun, W. H . Steric and electronic modulation of iron catalysts as a route to remarkably high molecular weight linear polyethylenes . Dalton Trans. , 2019 . 48 17488 - 17498 . DOI: 10.1039/C9DT03880A http://doi.org/10.1039/C9DT03880A .

Mahmood, Q.; Yue, E.; Guo, J.; Zhang, W.; Ma, Y.; Hao, X.; Sun, W. H . Nitro-functionalized bis(imino)pyridylferrous chlorides as thermo-stable precatalysts for linear polyethylenes with high molecular weights . Polymer , 2018 . 159 124 - 137 . DOI: 10.1016/j.polymer.2018.11.016 http://doi.org/10.1016/j.polymer.2018.11.016 .

Ba, J.; Du, S.; Yue, E.; Hu, X.; Flisak, Z.; Sun, W. H . Constrained formation of 2-(1-(arylimino)ethyl)-7-arylimino-6,6-dimethylcyclopentapyridines and their cobalt(II) chloride complexes: synthesis, characterization and ethylene polymerization . RSC Adv. , 2015 . 5 32720 - 32729 . DOI: 10.1039/C5RA04722F http://doi.org/10.1039/C5RA04722F .

Appukuttan, V. K.; Liu, Y.; Son, B. C.; Ha, C . S.; Suh, H.; Kim, I. Iron and cobalt complexes of 2,3,7,8-tetrahydroacridine-4,-5(1 H ,6 H )-diimine sterically modulated by substituted aryl rings for the selective oligomerization to polymerization of ethylene . Organometallics , 2011 . 30 2285 - 2294 . DOI: 10.1021/om2000629 http://doi.org/10.1021/om2000629 .

Sun, W. H.; Kong, S.; Chai, W.; Shiono, T.; Redshaw, C.; Hu, X.; Guo, C.; Hao, X . 2-(1-(Arylimino)ethyl)-8-arylimino-5,6,7-trihydroquinolylcobalt dichloride: synthesis and polyethylene wax formation . Appl. Catal. Gen. , 2012 . 447 - 448 . .

Huang, F.; Zhang, W.; Yue, E.; Liang, T.; Hu, X.; Sun, W. H . Controlling the molecular weights of polyethylene waxes using the highly active precatalysts of 2-(1-aryliminoethyl)-9-arylimino-5,6,7,8-tetrahydrocycloheptapyridylcobalt chlorides: synthesis, characterization and catalytic behavior . Dalton Trans. , 2016 . 45 657 - 666 . DOI: 10.1039/C5DT03779D http://doi.org/10.1039/C5DT03779D .

Wang, Z.; Solan, G. A.; Mahmood, Q.; Liu, Q.; Ma,Y.; Hao, X.; Sun, W. H . Bis(imino)pyridines incorporating doubly fused eight-membered rings as conformationally flexible supports for cobalt ethylene polymerization catalysts . Organometallics , 2018 . 37 380 - 389 . DOI: 10.1021/acs.organomet.7b00809 http://doi.org/10.1021/acs.organomet.7b00809 .

Zhang, Q.; Wu, N.; Xiang, J.; Solan, G. A. Suo, H.; Ma, Y.; Liang, T.; Sun, W. H . Bis-cycloheptyl-fused bis(imino)pyridine-cobalt catalysts for PE wax formation: positive effects of fluoride substitution on catalytic performance and thermal stability . Dalton Trans. , 2020 . 49 9425 - 9437 . DOI: 10.1039/D0DT01876G http://doi.org/10.1039/D0DT01876G .

Zhang, Q.; Zhang, R.; Han, M.; Yang, W.; Liang, T.; Sun, W. H . 4,4’-Difluorobenzhydryl-modified bis(imino)-pyridyliron(II) chlorides as thermally stable precatalysts for strictly linear polyethylenes with narrow dispersities . Dalton Trans. , 2020 . 49 7384 - 7396 . DOI: 10.1039/D0DT01344G http://doi.org/10.1039/D0DT01344G .

Zhao, W.; Yu, J.; Song, S.; Yang, W.; Liu, H.; Hao, X.; Redshaw, C.; Sun, W. H . Controlling the ethylene polymerization parameters in iron pre-catalysts of the type 2-[1-(2,4-dibenzhydryl-6-methyl- phenylimino)ethyl]-6-[1-(arylimino)ethyl] pyridyliron dichloride . Polymer , 2012 . 53 130 - 137 . DOI: 10.1016/j.polymer.2011.11.024 http://doi.org/10.1016/j.polymer.2011.11.024 .

Cao, X.; He, F.; Zhao, W.; Cai, Z.; Hao, X.; Shiono, T.; Redshaw, C.; Sun, W. H . 2-[1-(2,6-Dibenzhydryl-4-chlorophenylimino)ethyl]-6-[1-(arylimino)ethyl] pyridyliron(II) dichlorides: synthesis, characterization and ethylene polymerization behavior . Polymer , 2012 . 53 1870 - 1880 . DOI: 10.1016/j.polymer.2012.02.050 http://doi.org/10.1016/j.polymer.2012.02.050 .

Zhang, Q.; Ma, Y.; Suo, H.; Solan, G. A.; Liang, T.; Sun, W. H . Co-catalyst effects on the thermal stability/activity of N,N,N -co ethylene polymerization catalysts bearing fluoro-substituted N -2,6-dibenzhydrylphenyl groups . Appl. Organomet. Chem. , 2019 . 33 e5134 .

Views

126

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

High Temperature Iron Ethylene Polymerization Catalysts Bearing N,N,N'-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines

Modulating Molecular Weight of Polyethylenes from Oligomer to Polymer Using Highly Thermal Stable Cationic α-Diimine Palladium Complexes

Effect of Graphene/Nickel-iron Layered Double Hydroxide Hybrids on the Thermal Decomposition and Flame Retardancy of Acrylonitrile-butadiene-styrene Copolymer Composites

Bioinspired Zinc-doped Nano Hydroxyapatite Reinforced Poly(lactic acid) Composites for Bone Repair

pH-Responsive L-Cysteine-conjugated Polydopamine Nanocarriers for Controlled Release of Emamectin Benzoate against Pieris brassicae

Related Author

Chantsalnyam Bariashir

Qiu-Yue Zhang

Bayasgalan Ulambayar

Gregory A. Solan

Tong-Ling Liang

Wen-Hua Sun

Feng-Bin Liu

Chun-Yu Zhang

Related Institution

Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar

Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences

State Key Laboratory of Advanced Optical Polymer and Manufacturing Technology, Key Laboratory of Rubber-Plastics, Ministry of Education, School of Polymer Science and Engineering, Qingdao University of Science & Technology

State Key Laboratory of High-Efficiency Special Cable Technology, Shanghai Electric Cable Research Institute Co., Ltd.

State Key Laboratory of Fire Science, University of Science and Technology of China

⁰

Investigating the Effects of Para-methoxy Substitution in Sterically Enhanced Unsymmetrical Bis(arylimino)pyridine-cobalt Ethylene Polymerization Catalysts

DOI：10.1007/s10118-022-2670-z

摘要

Abstract

关键词

Keywords

references