High Temperature Iron Ethylene Polymerization Catalysts Bearing <italic style="font-style: italic">N,N,N'</italic>-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines

Chantsalnyam Bariashir; Qiu-Yue Zhang; Bayasgalan Ulambayar; Gregory A. Solan; Tong-Ling Liang; Wen-Hua Sun

doi:10.1007/s10118-023-3037-9

Your Location：

Home >

Browse articles >

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

RESEARCH ARTICLE | Updated：2024-01-12

- High Temperature Iron Ethylene Polymerization Catalysts Bearing N,N,N'-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines
  Enhanced Publication
- High Temperature Iron Ethylene Polymerization Catalysts Bearing N,N,N'-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines
- 高分子科学（英文版） 2024年42卷第2期页码：188-201
- Affiliations：
  
  a.Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar 13330, Mongolia
  b.Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, 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：
  
  gas8@leicester.ac.uk (G.A.S.)
  whsun@iccas.ac.cn (W.H.S.)
- Funds：
  
  G.A.S. thanks the Chinese Academy of Sciences for a President's International Fellowship for Visiting Scientists.;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-023-3037-9.
- DOI：10.1007/s10118-023-3037-9
  中图分类号：
Scan for full text
Bariashir, C.; Zhang, Q. Y.; Ulambayar, B.; Solan, G. A.; Liang, T. L.; Sun, W. H. High temperature iron ethylene polymerization catalysts bearing N,N,N'-2-(1-(2,4-dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines. Chinese J. Polym. Sci. 2024, 42, 188–201

Chantsalnyam Bariashir, Qiu-Yue Zhang, Bayasgalan Ulambayar, et al. High Temperature Iron Ethylene Polymerization Catalysts Bearing N,N,N'-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines[J]. Chinese Journal of Polymer Science, 2024,42(2):188-201.
Bariashir, C.; Zhang, Q. Y.; Ulambayar, B.; Solan, G. A.; Liang, T. L.; Sun, W. H. High temperature iron ethylene polymerization catalysts bearing N,N,N'-2-(1-(2,4-dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines. Chinese J. Polym. Sci. 2024, 42, 188–201 DOI： 10.1007/s10118-023-3037-9.

Chantsalnyam Bariashir, Qiu-Yue Zhang, Bayasgalan Ulambayar, et al. High Temperature Iron Ethylene Polymerization Catalysts Bearing N,N,N'-2-(1-(2,4-Dibenzhydryl-6-fluorophenylimino)ethyl)-6-(1-(arylphenylimino)ethyl)pyridines[J]. Chinese Journal of Polymer Science, 2024,42(2):188-201. DOI： 10.1007/s10118-023-3037-9.

摘要

The combined effect of an electron withdrawing fluoride and a sterically bulk benzhydryl group at the ,ortho,-sites of one ,N,-aryl group in the title iron precatalyst, allows for very high polymerization activity at an operating temperature of 80 oC.

Abstract

The ,N,N,N',-ferrous chloride complexes, [2-{CMeN(2,4-(CHPh),2,-6-FC,6,H,2,)}-6-(CMeNAr)C,5,H,3,N]FeCl,2, (Ar ,=, 2,6-Me,2,C,6,H,3,Fe1, 2,6-Et,2,C,6,H,3,Fe2, 2,6-,i,Pr,2,C,6,H,3,Fe3, 2,4,6-Me,3,C,6,H,2,Fe4, and 2,6-Et,2,-4-MeC,6,H,2,Fe5,), each possessing one ,N,-2,4-dibenzhydryl-6-fluorophenyl group, were readily synthesized from their respective unsymmetrical bis(imino)pyridines,L1,–,L5,. Structural identification of ,Fe2, highlighted the variation in the steric properties provided by the dissimilar ,N,-aryl groups. Following pre-treatment with either MAO or MMAO, complexes ,Fe1,–,Fe5, all displayed, at an operating temperature of 80 °C, high activities for ethylene polymerization with levels falling in the order: ,Fe4,>,Fe1,>,Fe5,>,Fe2,>,Fe3,. Notably,Fe4,/MAO displayed the highest activity of 1.94×10,7, g,PE,·mol,Fe,−1,·h,−1, of the study with only a modest loss in performance at 90 °C. Generally, the resulting polyethylenes were highly linear (,T,m, range: 122–132 °C), narrowly disperse and of low molecular weight (,M,w, range: 6.73−46.04 kg·mol,−1,), with the most sterically hindered ,Fe3, forming the highest molecular weight polymer of the series. End-group analysis by ,1,H- and ,13,C-NMR spectroscopy revealed saturated alkyl (,n,-propyl and ,i,-propyl) and unsaturated vinyl chain ends indicative of the role of both ,β,-H elimination and chain transfer to aluminum as termination pathways. By comparison with previously reported iron precatalysts with similar tridentate ligand skeletons, it is evident that the introduction of a large benzhydryl group in combination with a fluorine as the ,ortho,-substituents of one ,N,-aryl group has the effect of enhancing thermal stability of the iron polymerization catalyst whilst maintaining appreciable polymer molecular weight.

关键词

Keywords

Iron catalystEthylene polymerizationLinear polyethyleneFluoride effectThermal stability

references

Bianchin,C.;Giambastiani,G.;Rios,I.G.;Mantovani,G.;Meli,A.;Segarra,A.M.Ethyleneoligomerization,homopolymerizationandcopolymerizationbyironandcobaltcatalystswith2,6-(bis-organylimino)pyridylligands.Coord. Chem. Rev.2006, 250,1391–1418..

Gibson,V.C.;Redshaw,C.;Solan,G.A.Bis(imino)pyridines:surprisinglyreactiveligandsandagatewaytonewfamiliesofcatalysts.Chem. Rev.2007, 107,1745–1776..

Makio,H;Terao,H.;Iwashita,A.;Fujita,T.FIcatalystsforolefinpolymerization—acomprehensivetreatment.Chem. Rev.2011, 111,2363–2449..

Wang,Z.;Liu,Q;Solan,G.A.;Sun,W.H.RecentadvancesinNi-mediatedethylenechaingrowth:Nimine-donorligandeffectsoncatalyticactivity,thermalstabilityandoligo-/polymerstructure.Coord. Chem. Rev.2017, 350,68–83..

Wang,Z.;Solan,G.A.;Zhang,W.;Sun,W.H.Carbocyclic-fused N,N,N-pincerligandsasring-strainadjustablesupportsforironandcobaltcatalystsinethyleneoligo-/polymerization.Coord. Chem. Rev.2018, 363,92–108..

Bariashir,C.;Huang,C.;Solan,G.A.;Sun,W.H.Recentadvancesinhomogeneouschromiumcatalystdesignforethylenetri-,tetra-,oligo-andpolymerization.Coord. Chem. Rev.2019, 385,208–229..

Champouret,Y.;Hashmi,O.H.;Visseaux,M.Discreteiron-basedcomplexes:applicationsinhomogeneouscoordination-insertionpolymerizationcatalysis.Coord. Chem. Rev.2019, 390,127–170..

Yuan,S.F.;Yan,Y.;Solan,G.A.;Ma,Y.;Sun,W.H.Recentadvancementsin N-ligatedgroup4molecularcatalystsforthe(co)polymerizationofethylene.Coord. Chem. Rev.2020, 411,213254..

Phillips,A.M.F.;Suo,H.;Silva,M.F.C.G.;Pombeiro,A.J.L.;Sun,W.H.Recentdevelopmentsinvanadium-catalyzedolefincoordinationpolymerization.Coord. Chem. Rev.2020, 416,213332..

Wang,Y.;Zhang,W.;Wang,X.;Ma,Y.;Sun,W.H.Ironcomplexcatalystsinethylenereactivity:fromconcepttocommercialization.Acta Polymerica Sinica (in Chinese)2023, 54,564–583..

Wang,Z.;Mahmood,Q.;WenjuanZhang,W.;Sun,W.H.Recentprogressonthetridentateironcomplexcatalystsforethyleneoligo-/polymerization.Adv. Organomet. Chem.2023, 79,41–83..

Britovsek,G.J.;Dorer,B.A.;Gibson,V.C.;Kimberley,B.S.;Solan,G.A., 1997 ,(BPChemicals)WO9912981.

Bennett,A.M.A., 1998 ,(DuPontComp)WO9951550.

Small.B.L.;Brookhart,M.;Bennett,A.M.A.Highlyactiveironandcobaltcatalystsforthepolymerizationofethylene.J. Am. Chem. Soc.1998, 120,4049–4050..

Britovsek,G.J.P.;Gibson,V.C.;Kimberley,B.S.;Maddox,P.J.;McTavish,S.J.;Solan,G.A.;White,A.J.P.;Williams,D.J.Novelolefinpolymerizationcatalystsbasedonironandcobalt.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.;Stromberg,S.;White,A.J.P.;Williams,D.J.Ironandcobaltethylenepolymerizationcatalystsbearing2,6-bis(Imino)pyridylligands:synthesis,structures,andpolymerizationstudies.J. Am. Chem. Soc.1999, 121,8728–8740..

Small,B.L.;Brookhart,M.Iron-basedcatalystswithexceptionallyhighactivitiesandselectivitiesforoligomerizationofethylenetolinear α-olefins.J. Am. Chem. Soc.1998, 120,7143–7144..

Britovsek,G.J.P.;Mastroianni,S.;Solan,G.A.;Baugh,S.P.D.;Redshaw,C.;Gibson,V.C.;White,A.J.P.;Williams,D.J.;Elsegood,M.R.J.Oligomerisationofethylenebybis(imino)pyridylironand-cobaltcomplexes.Chem. Eur. J.2000, 6,2221–2231..

Ma,Z.;Wang,H.;Qui,J.;Xu,D.;Hu,Y.Anovelhighlyactiveiron/2,6-bis(imino)pyridylcatalystforethylenepolymerization.Macromol. Rapid Commun.2001, 22,1280–1283..

Abu-Surrah,A.S.;Lappalainen,K.;Piironen,U.;Lehmus,P.;Repo,T.;Leskelä,M.Newbis(imino)pyridine-iron(II)-andcobalt(II)-basedcatalysts:synthesis,characterizationandactivitytowardspolymerizationofethylene.J. Organomet. Chem.2002, 648,55–61..

Gibson,V.C.;Spitzmesser,S.K.Advancesinnon-metalloceneolefinpolymerizationcatalysis.Chem. Rev.2003, 103,283–315..

Chen,Y.;Chen,R.;Qian,C.;Dong,X.;Sun,J.Halogen-substituted2,6-bis(imino)pyridylironandcobaltcomplexes:highlyactivecatalystsforpolymerizationandoligomerizationofethylene.Organometallics2003, 22,4312–4321..

Chen,Y.;Qian,C.;Sun,J.Fluoro-substituted2,6-bis(imino)pyridylironandcobaltcomplexes:high-activityethyleneoligomerizationcatalysts.Organometallics2003, 22,1231–1236..

Ivanchev,S.S.;Yakimansky,A.V.;Rogozin,D.G.Quantum-chemicalcalculationsoftheeffectofcycloaliphaticgroupsin α-diimineandbis(imino)pyridineethylenepolymerizationprecatalystsontheirstabilitieswithrespecttodeactivationreactions.Polymer2004, 45,6453–6459..

Zhang,T.;Sun,W.H.;Li,T.;Yang,X.Influenceofelectroniceffectoncatalyticactivityofbis(imino)pyridylFe(II)andbis(imino)pyrimidylFe(II)complexes.J. Mol. Catal. A: Chem.2004, 218,119–124..

Zhong,L.;Li,G.;Liang,G.;Gao,H.;Wu,Q.Enhancingthermalstabilityandlivingfashionin α-diimine−nickel-catalyzed(co)polymerizationofethyleneandpolarmonomerbyincreasingthestericbulkofligandbackbone.Macromolecules2017, 50,2675–2682..

Zada,M.;Vignesh,A.;Suo,H.;Ma,Y.;Liu,H.;Sun,W.H.N,N,N-typeiron(II)complexesconsistingstericallyhindereddibenzocycloheptylgroup:synthesisandcatalyticactivitytowardsethylenepolymerization.Mol. Catal. 2020 ,492,110981..

McTavish,S.;Britovsek,G.J.;Smit,T.M.;Gibson,V.C.;White,A.J.P.;Williams,D.J.Iron-basedethylenepolymerizationcatalystssupportedbybis(imino)pyridineligands:derivatization viadeprotonation/alkylationattheketiminemethylposition.J. Mol. Catal. A: Chem.2007, 261,293–300..

Smit,T.M.;Tomov,A.K.;Britovsek,G.J.P.;Gibson,V.C.;White,A.J.P.;Williams,D.J.Theeffectofimine-carbonsubstituentsinbis(imino)pyridine-baseethylenepolymerisationcatalystsacrossthetransitionseries.Catal. Sci. Technol.2012, 2,643–655..

Wang,G.;Jiang,X.;Zhao,W.;Sun,W.-H.;Yao,W.;He,A.CatalyticbehaviorofCo(II)complexeswith2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridineligandsonisoprenestereospecificpolymerization.J. Appl. Polym. Sci. 2014 ,39703..

Zhang,W.;Chai,W.;Sun,W.-H.;Hu,X.;Redshaw,C.;Hao,X.2-(1-(Arylimino)ethyl)-8-arylimino-5,6,7-trihydroquinolineiron(II)chloridecomplexes:synthesis,characterization,andethylenepolymerizationbehavior.Organometallics 2012 ,31,5039–5048..

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-trihydroquinolylcobaltdichloride:synthesisandpolyethylenewaxformation.Appl. Catal. A 2012 ,447–448,67–73..

Zhang,R.;Huang,Y.;Solan,G.A.;Zhang,W.;Hu,X.;Hao,X.;Sun,W.-H.gem-Dimethyl-substitutedbis(imino)-dihydroquinolinesasthermallystablesupportsforhighlyactivecobaltcatalyststhatproducelinearPEwaxes.Dalton Trans. 2019 ,48,8175–8185..

Huang,F.;Xing,Q.;Liang,T.;Flisak,Z.;Ye,B.;Hu,X.;Yang,W.;Sun,W.H.2-(1-Aryliminoethyl)-9-arylimino-5,6,7,8-tetrahydrocycloheptapyridyliron(II)dichloride:synthesis,characterization,andthehighlyactiveandtunableactivespeciesinethylenepolymerization.Dalton Trans. 2014 ,43,16818–16829..

Huang,F.;Zhang,W.;Yue,E.;Liang,T.;Hu,X.;Sun,W.H.Controllingthemolecularweightsofpolyethylenewaxesusingthehighlyactiveprecatalystsof2-(1-aryliminoethyl)-9-arylimino-5,6,7,8-tetrahydrocycloheptapyridylcobaltchlorides:synthesis,characterization,andcatalyticbehavior.Dalton Trans.2016, 45,657–666..

Huang,C.;Huang,Y.;Ma,Y.;Solan,G.A.;Sun,Y.;Hu,X.;Sun,W.-H.Cycloheptyl-fused N,N,N’-chromiumcatalystswithselectivityforvinyl-terminatedpolyethylenewaxes:thermaloptimizationandpolymerfunctionalization.Dalton Trans.2018, 47,13487–13497..

Guo,J.;Wang,Z.;Zhang,W.;Oleynik,I.I.;Vignesh,A.;Oleynik,I.V.;Hu,X.;Sun,Y.;Sun,W.H.Highlylinearpolyethylenesachievedusingthermo-stableandefficientcobaltprecatalystsbearingcarbocyclic-fusedNNN-pincerligand.Molecules2019, 24,1176..

Guo,J.;Zhang,Q.;Oleynik,I.I.;Solan,G.A.;Oleynik,I.V.;Liang,T.;Sun,W.H.Probingtheeffectof ortho-cycloalkylringsizeonactivityandthermostabilityincycloheptyl-fused N,N,N-ironethylenepolymerizationcatalysts.Dalton Trans.2020, 49,136–146..

Han,M.;Zhang,Q.;Oleynik,I.I.;Suo,H.;Solan,G.A.;Oleynik,I.V.;Ma,Y.;Liang,T.;Sun,W.-H.Highmolecularweightpolyethylenesofnarrowdispersitypromotedusingbis(arylimino)cyclohepta[ b]pyridine-cobaltcatalysts ortho-substitutedwithbenzhydryl&cycloalkylgroups.Dalton Trans.2020, 49,4774–4784..

Du,S.;Wang,X.;Zhang,W.;Flisak,Z.;Sun,Y.;Sun,W.H.Apracticalethylenepolymerizationforvinyl-polyethylenes:synthesis,characterizationandcatalyticbehaviorof α,α’-bisimino-2,3:5,6-bis(pentamethylene)pyridylironchlorides.Polym. Chem.2016, 7,4188–4197..

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

Huang,C.;Du,S.;Solan,G.A.;Sun,Y.;Sun,W.H.FrompolyethylenewaxestoHDPEusingan α,α’-bis(arylimino)-2,3:5,6-bis(pentamethylene)pyridyl-chromium(III)chloridepre-catalystinethylenepolymerization.Dalton Trans.2017, 46,6948–6957..

Suo,H.;Oleynik,I.I.;Bariashir,C.;Oleynik,I.V.;Wang,Z.;Solan,G.A.;Ma,Y.;Liang,T.;Sun,W.H.Strictlylinearpolyethyleneusingco-catalystschelatedbyfusedbis(arylimino)pyridines:Probingortho-cycloalkylring-sizeeffectsonmolecularweight.Polymer2018, 149,45–54..

Bariashir,C.;Wang,Z.;Suo,H.;Zada,M.;Solan,G.A.;Ma,Y.;Liang,T.;Sun,W.H.Narrowdispersedlinearpolyethyleneusingcobaltcatalystsbearingcycloheptyl-fusedbis(imino)pyridines;probingtheeffectsof ortho-benzhydrylsubstitution.Eur. Polym. J.2019, 110,240–251..

Bariashir,C.;Wang,Z.;Solan,G.A.;Huang,C.;Hao,X.;Sun,W.-H.Chromiumethylenepolymerizationcatalystsbearingstericallyenhanced α,α′-bis(imino)-2,3:5,6-bis(pentamethylene)pyridines:tuningactivityandmolecularweight.Polymer2019, 171,87–95..

Bariashir,C.;Wang,Z.;Ma,Y.;Vignesh,A.;Hao,X.;Sun,W.-H.Finelytuned α,α′-bis(arylimino)-2,3:5,6-bis(pentamethylene)pyridine-basedpracticalironprecatalystsfortargetinghighlylinearandnarrowdispersivepolyethylenewaxeswithvinylends.Organometallics2019, 38,4455–4470..

Zhang,Q.;Wu,N.;Xiang,J.;Solan,G.A.;Suo,H.;Ma,Y.;Liang,T.;Sun,W.H.4,4’-Difluorobenzhydryl-modifiedbis(imino)-pyridyliron(II)chloridesasthermallystableprecatalystsforstrictlylinearpolyethyleneswithnarrowdispersity.Dalton Trans. 2020 ,49,9425–9437..

Suo,H.;Li,Z.;Oleynik,I.V.;Wang,Z.;Oleynik,I.I.;Ma,Y.;Liu,Q.;Sun,W.H.AchievingstrictlylinearpolyethylenesbytheNNN-Feprecatalystsfinelytunedwithdifferentsizesof ortho-cycloalkylsubstituents.Appl. Organomet. Chem.2020, 34,e5937..

Zhang,Q.;Yang,W.;Wang,Z.;Solan,G.A.;Liang,T.;Sun,W.-H.Doublyfused N,N,N-ironethylenepolymerizationcatalystsappendedwithfluoridesubstituents;probingcatalyticperformance viaacombinedexperimentalandMLRstudy.Catal. Sci. Technol.2021, 11,4605–4618..

Wang,Z.;Solan,G.A.;Mahmood,Q.;Liu.Q.;Ma,Y.;Hao,X.;Sun,W.H.Bis(imino)pyridinesincorporatingdoublyfusedeight-memberedringsasconformationallyflexiblesupportsforcobaltethylenepolymerizationcatalysts.Organometallics2018, 37,380–389..

Wang,Z.;Zhang,R.;Zhang,W.;Solan,G.A.;Liu,Q.;Liang,T.;Sun,W.-H.Enhancingthermostabilityofironethylenepolymerizationcatalyststhrough N,N,N-chelationofdoublyfused α,α′-bis(arylimino)-2,3:5,6-bis(hexamethylene)pyridines.Catal. Sci. Technol.2019, 9,1933–1943..

Wang,Z.;Ma,Y.;Guo,J.;Liu,Q.;Solan,G.A.;Liang,T.;Sun,W.H.Bis(imino)pyridinesfusedwith6-and7-memberedcarbocylicringsas N,N,N-scaffoldsforcobaltethylenepolymerizationcatalysts.Dalton Trans.2019, 48,2582–2591..

Wang,Z.;Solan,G.A.;Ma,Y.;Liu,Q.;Liang,T.;Sun,W.H.Fusingcarbocyclesofinequivalentringsizetoabis(imino)pyridine-ironethylenepolymerizationcatalyst;distinctiveeffectsonactivity,PEmolecularweightanddispersity.Research 2019 ,1–15..

Huang,F.;Zhang,W.;Sun,Y.;Hu,X.;Solan,G.A.;Sun,W.H.Thermallystableandhighlyactivecobaltprecatalystsforvinyl-polyethyleneswithnarrowpolydispersities:integratingfused-ringandimino-carbonprotectionintoliganddesign.New. J. Chem.2016, 40,8012–8023..

Zhang,Y.;Suo,H.;Huang,F.;Liang,T.;Hu,X.;Sun,W.H.Thermo-stable2-(arylimino)benzylidene-9-arylimino-5,6,7,8-tetrahydrocyclohepta[b]pyridyliron(II)precatalyststowardethylenepolymerizationandhighlylinearpolyethylenes.J. Polym. Sci., Part A: Polym. Chem.2017, 55,830–842..

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,characterizationandethylenepolymerizationbehavior.Polymer 2012 ,1870–1880..

Zhang,Q.;Zhang,R.;Han,M.;Yang,W.;Liang,T.;Sun,W.H.4,4’-Difluorobenzhydryl-modifiedbis(imino)pyridyliron(II)chloridesasthermallystableprecatalystsforstrictlylinearpolyethyleneswithnarrowdispersity.Dalton Trans. 2020 ,49,7384–7396..

Mahmood,Q.;Guo,J.;Zhang,W.;Ma,Y.;Liang,T.;Sun,W.H.Concurrentlyimprovingthethermalstabilityandactivityofferrousprecatalystsfortheproductionofsaturated/unsaturatedpolyethylene.Organometallics2018, 37,957–970..

Han,M.;Oleynik,I.I.;Ma,Y.;Oleynik,I.V.;Solan,G.A.;Hao,X.;Sun,W.H.Modulatingthermostabilityandproductivityofbenzhydryl-substitutedbis(imino)pyridine-ironC2H4polymerizationcatalyststhroughortho-C nH2 n−1(n=5,6,8,12)ringsizeadjustment.Eur. J. Inorg. Chem. 2022 , 2022,e202200224..

Gibson,V.C.;Solan,G.A.Catalysis without precious metals,ed.byBullock,R.M.,Weinheim,Germany, 2010 ,p.111–141..

Mitchell,N.E.;Anderson.W.C.;Long,J.B.K.Mitigatingchain-transferandenhancingthethermalstabilityofCo-basedolefinpolymerizationcatalyststhroughstericallydemandingligands.J. Polym. Sci., Part A: Polym. Chem.2017, 55,3990–3995..

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(ironorcobalt)complexes:synthesis,characterization,andethylenepolymerizationbehavior.Macromol. Chem. Phys. 2014 ,215,1797–1809..

Yu,J.;Liu,H.;Zhang,W.;Hao,X.;Sun,W.H.Accesstohighlyactiveandthermallystableironprocatalystsusingbulky2-[1-(2,6-dibenzhydryl-4-methylphenylimino)ethyl]-6-[1-(arylimino)ethyl]pyridineligands.Chem. Commun.2011, 47,3257–3259..

Zhao,W.;Yue,E.;Wang,X.;Yang,W.;Chen,Y.;Hao,X.;Cao,X.;Sun,W.H.Activityandstabilityspontaneouslyenhancedtowardethylenepolymerizationbyemploying2-(1-(2,4-dibenzhydrylnaphthylimino)ethyl)-6-(1-(arylimino)ethyl)pyridyliron(II)dichlorides.J. Polym. Sci., Part A: Polym. Chem.2017, 55,988–996..

Mahmood,Q.;Yue,E.;Zhang,W.;Guo,J.;Zhang,W.;Ma,Y.;Hao,X.;Sun,W.H.Nitro-functionalizedbis(imino)pyridylferrouschloridesasthermo-stableprecatalystsforlinearpolyethyleneswithhighmolecularweights.Polymer2018, 159,124–137..

Zhao,W.;Yu,J.;Song,S.;Yang,W.;Liu,H.;Hao,X.;Redshaw,C.;Sun,W.H.Controllingtheethylenepolymerizationparametersinironpre-catalystsofthetype2-[1-(2,4-dibenzhydryl-6-methylphenylimino)ethyl]-6-[1-(arylimino)ethyl]pyridylirondichloride.Polymer2012, 53,130–137..

Kaul,F.A.R.;Puchta,G.T.;Frey,G.D.;Herdtweck,E.;Herrmann,W.A.Iminopyridinecomplexesof3Dmetalsforethylenepolymerization:comparativestructuralstudiesandligandsizecontrolledchaintermination.Organometallics2007, 26,988–999..

Guo,L.;Gao,H.;Zang,L.;Zhu,F.;Wu,Q.Anunsymmetricaliron(II)bis(imino)pyridylcatalystforethylenepolymerization:effectofabulky orthosubstituentonthethermostabilityandmolecularweightofpolyethylene.Organometallics2010, 29,2118–2125..

Wang,S.;Li,B.;Liang,T.;Redshaw,C.;Li,Y.;Sun,W.H.Synthesis,characterizationandcatalyticbehaviortowardethyleneof2-[1-(4,6-dimethyl-2-benzhydryl-phenylimino)ethyl]-6-[1-(arylimino)ethyl]-pyridylmetal(ironorcobalt)chlorides.Dalton Trans.2013, 42,9188–9197..

Yan,Y.;Yuan,S.F.;Liu,M.;Solan,G.A.;Ma,Y.;Liang,T.;Sun,W.H.Investigatingtheeffectsof para-methoxysubstitutioninstericallyenhancedunsymmetricalbis(arylimino)pyridine-cobaltethylenepolymerizationcatalysts.Chinese J. Polym. Sci.2022, 40,266–279..

Guo,L.;Zhang,W.;Cao,F.;Jiang,Y.;Zhang,R.;Ma,Y.;Solan,G.A.;Sun,Y.;Sun,W.H.Remotedibenzocycloheptylsubstitutiononabis(arylimino)pyridyl-ironethylenepolymerizationcatalyst;enhancedthermalstabilityandunexpectedeffectsonpolymerproperties.Polym. Chem.2021, 12,4214–4225..

Bariashir,C.;Zhang,R.;Vignesh,A.;Ma,Y.;Liang,T.;Sun,W.H.Enhancingethylenepolymerizationof NNN-cobalt(II)precatalystsadornedwithafluoro-substituent.ACS Omega2021, 6,4448–4460..

Sheldrick,G.M.SHELXT–Integratedspace-groupandcrystal-structuredetermination.Acta Crystallogr.2015, A71,3−8..

Sheldrick,G.M.CrystalstructurerefinementwithSHELXL.Acta Crystallogr.2015, C71,3−8..

Zhang,Q.;Zuo,Z.;Ma,Y.;Liang,T.;Yang,X.;Sun,W.H.Fluorinated2,6-bis(arylimino)pyridylironcomplexestargetingbimodaldispersivepolyethylenes:probingchainterminationpathwaysviaacombinedexperimentalandDFTstudy.Dalton Trans.2022, 51,8290–8302..

Crans,D.C.;Tarlton,M.L.;McLauchlan,C.C.Trigonalbipyramidalorsquarepyramidalcoordinationgeometry?Investigatingthemostpotentgeometryforvanadiumphosphataseinhibitors.Eur. J. Inorg. Chem. 2014 ,4450–4468..

Cantalupo,S.A.;Ferreira,H.E.;Bataineh,E.;King,A.J.;Petersen,M.V.;Wojtasiewicz,T.;DiPasquale,A.G.;Rheingold,A.L.;Doerrer,L.H.SynthesiswithstructuralandelectroniccharacterizationofhomolepticFe(II)-andFe(III)-fluorinatedphenolatecomplexes.Inorg. Chem.2011, 50,6584–6596..

Addison,A.W.;Rao,T.N.;Reedijk,J.;Van,R.J.;Verschoor,G.C.Synthesis,structure,andspectroscopicpropertiesofcopper(II)compoundscontainingnitrogen-sulphurdonorligands;thecrystalandmolecularstructureofaqua[l,7-bis(N-methylbenzimidazol-2'-yl)-2,6-dithiaheptane]copper(II)perchlorate.J. Chem. Soc., Dalton Trans.1 984 ,1349–1356..

Britovsek,G.P.;Gibson,V.C.;Kimberley,B.S.;Mastroianni,S.;Redshaw,C.;Solan,G.A.;White,A.J.P.;Williams,D.J.Bis(imino)pyridylironandcobaltcomplexes:theeffectofnitrogensubstituentsonethyleneoligomerisationandpolymerization.J. Chem. Soc., Dalton Trans. 2001 ,1639–1644..

Britovsek,G.J.P.;Gibson,V.C.;Spitzmesser,S.K.;Tellmann,K.P.;White,A.J.P.;Williams,D.J.Cationic2,6-bis(imino)pyridineironandcobaltcomplexes:synthesis,structures,ethylenepolymerisationandethylene/polarmonomerco-polymerisationstudies.J. Chem. Soc., Dalton Trans. 2002 ,1159–1171..

Deng,L.;Margl,P.;Ziegler,T.Mechanisticaspectsofethylenepolymerizationbyiron(II)-bisiminepyridinecatalysts:acombineddensityfunctionaltheoryandmolecularmechanicsstudy.J. Am. Chem. Soc.1999, 121,6479–6487..

Wang,Q.;Yang,H.;Fan,Z.Efficientactivatorsforanironcatalystinthepolymerizationofethylene.Macromol. Rapid Commun.2002, 23,639–642..

Rhinehart,J.L.;Brown,L.A.;Long,K.ArobustNi(II) α-diiminecatalystforhightemperatureethylenepolymerization.J. Am. Chem. Soc.2013, 135,16316–16319..

Shen,Y.;Zhu,S.Atomtransferradicalpolymerizationofmethylmethacrylatemediatedbycopperbromide-tetraethyldiethylenetriaminegraftedonsolubleandrecoverablepoly(ethylene- b-ethyleneglycol)supports.Macromolecules2001, 34,8603–8609..

Britovsek,G.J.P.;Gibson,V.C.;Hoarau,O.D.;Spitzmesser,S.K.;White,A,J.P.;Williams,D.J.Ironandcobaltethylenepolymerizationcatalysts:variationsonthecentraldonor.Inorg. Chem.2003, 42,3454–3465..

Semikolenova,N.V.;Sun,W.H.;Soshnikov,I.E.;Matsko,M.A.;Kolesova,O.V.;Zakharov,V.A.;Bryliakov,K.P.Originof“multisite-like”ethylenepolymerizationbehaviorofthesingle-sitenonsymmetricalbis(imino)pyridineiron(II)complexinthepresenceofmodifiedmethylaluminoxane.ACS Catal.2017, 7,2868–2877..

Sun,W.H.;Tang,X.;Cao,T.;Wu,B.;Zhang,W.;Ma,H.Synthesis,characterization,andethyleneoligomerizationandpolymerizationofferrousandcobaltous2-(ethylcarboxylato)-6-iminopyridylcomplexes.Organometallics2004, 23,5037–5047..

Gates,D.P.;Svejda,S.A.;Oñate,E.;Killian,C.M.;Johnson,L.K.;White,P.S.;Brookhart,M.Synthesisofbranchedpolyethyleneusing( α-diimine)nickel(II)catalysts:influenceoftemperature,ethylenepressure,andligandstructureonpolymerproperties.Macromolecules2000, 33,2320–2334..

Popeney,C.S.;Rheingold,A.L.;Guan,Z.Nickel(II)andpalladium(II)polymerizationcatalystsbearingafluorinatedcyclophaneligand:stabilizationofthereactiveintermediate.Organometallics2009, 28,4452–4463..

Lee,L.S.;Ou,H.J.;Hsu,H.F.Theexperimentsandcorrelationsofthesolubilityofethyleneintoluenesolvent.Fluid. Phase. Equilib.2005, 231,221–230..

Yu,J.;Huang,W.;Wang,L.;Redshaw,C.;Sun,W.H.2-[1-(2,6-Dibenzhydryl-4-methylphenyl-imino)ethyl]-6-[1-(arylimino)ethyl]-pyridylcobalt(II)dichlorides:synthesis,characterizationandethylenepolymerizationbehavior.Dalton Trans. 2011 ,40,10209–10214..

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,characterizationandethylenepolymerizationbehavior.Polym. Chem. 2012 ,3,787–793..

He,F.;Zhao,W.;Yang,W.;Cao,X.P.;Liang,T.;Redshaw,C.;Sun,W.H.2-[1-(2,6-dibenzhydryl-4-chlorophenylimino)ethyl]-6-[1-aryliminoethyl]pyridylcobaltdichlorides:synthesis,characterizationandethylenepolymerizationbehavior.J. Organomet. Chem. 2012 ,713,209–216..

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]pyridylcobaltdichlorides:synthesis,characterizationandethylenepolymerizationbehavior.J. Organomet. Chem. 2013 ,731,78–84..

Yuan,J.;Shi,W.B.;Kou,H.Z.Syntheses,crystalstructuresandmagnetismofazide-bridgedfive-coordinatebinuclearnickel(II)andcobalt(II)complexes.Transition Met. Chem.2015, 40,807–811..

Huang,C.;Zhang,Y.;Solan,G.A.;Ma,Y.;Hu,X.;Sun,Y.;Sun,W.H.Vinyl-polyethylenewaxeswithnarrowdispersityobtainedbyusingathermallyrobust[bis(imino)trihydroquinolyl]chromium.Catalyst Eur. J. Inorg. Chem. 2017 ,4158–4166..

Zhang,S.;Vystorop,I.;Tang,Z.;Sun,W.H.Bimetallic(ironorcobalt)complexesbearing2-methyl-2,4-bis(6-iminopyridin-2-yl)-1 H-1,5-benzodiazepinesforethylenereactivity.Organometallics2007, 26,2456–2460..

Zhang,S.;Sun,W.H.;Kuang,X.;Vystorop,I.;Yi,Unsymmetricbimetal(II)complexes:synthesis,structuresandcatalyticbehaviorstowardethylene.J. Organomet. Chem. 2007 ,692,5307–5316..

Sweet,G.E.;Bell,J.P.Multipleendothermmeltingbehaviorinrelationtopolymermorphology.J. Polym. Sci., Part A-21972, 10,1273–1283..

Hay,J.N.;Langford,J.L.;Lloyd,J.R.Variationinunitcellparametersofaromaticpolymerswithcrystallizationtemperature.Polymer1989, 30,489–493..

Bassett,D.C.;Hodge,A.M.;Olley,R.H.Lamellarmorphologiesinmelt-crystallizedpolyethylene.Discuss. Faraday Soc.1979, 68,218–224..

Bassett,D.C.;Hodge,A.M.Onlamellarorganizationincertainpolyethylenespherulites.Proc. R. Soc. London, Ser. A1978, 359,121–132..

Chung,J.S;Cebe,P.Meltingbehaviourofpoly(phenylenesulphide):2.Multiplestagemeltcrystallization.Polymer1992, 33,2325–2333..

Jie,S.;Zhang,D.;Zhang,T.;Sun,W.H.;Chen,J.;Ren,Q.;Liu,D.;Zheng,G.;Chen,W.Bridgedbispyridinyliminodinickel(II)complexes:syntheses,characterization,ethyleneoligomerizationandpolymerization.J. Organomet. Chem.2005, 690,1739–1749..

Zhang,Q.;Lin,W.;Liu,T.;Ye,Z.;Liang,T.;Sun,W.H.Fluorinatedstericallybulkymononuclearandbinuclear2-iminopyridylnickelhalidesforethylenepolymerization:effectsofligandframeworksandremotesubstituents.ACS Omega2021, 6,30157–30172..

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

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

Phosphine/Benzocyclone-based Neutral Nickel Catalysts for Ethylene Polymerization and Copolymerization with Polar Monomers

High-Performance α-Diimine Nickel Complexes for Facile Access of PE Elastomers with Exceptional Material Properties

Peculiarities of Ethylene Polymerization Reactions with Bis(imino)pyridyl Complexes of CoCl₂ and FeCl₂

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

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

DOI：10.1007/s10118-023-3037-9

摘要

Abstract

关键词

Keywords

references