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

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Chinese Journal of Polymer Science 2024年第2期42卷 202-212,I0007页

作者： Fei Wang Li Pan Vladislav A.Tuskaev Svetlana Ch.Gagieva Yue-Sheng Li Tianjin Key Lab of Composite&Functional Materials School of Material Science and EngineeringTianjin UniversityTianjin300072China Department of Chemistry Lomonosov Moscow State UniversityRussian Federation InstitutionLeninskie Gory 1Moscow119991Russian Federation A N Nesmeyanov Institute of Organoelement Compounds Russian Academy of SciencesVavilova st.28Moscow119991Russian Federation

The efficient Copolymerization of olefin with polar monomers using nickel-based catalysts presents a longstanding challenge. In this contribution, three phosphine-benzocyclone ligands and corresponding neutral nickel catalysts(Ni1: Ar = Ph;Ni2: Ar = 2-(C_(6)H_(5))C_(6)H_(4);Ni3: Ar = 2-[2',6'-(Me O)_(2)-C_(6)H3]C_(6)H_(4)) were prepared and applied for the ethylene polymerization and Copolymerization with polar monomers without any cocatalyst. The bulky substituent groups in complexes Ni2 and Ni3 contributed to high catalytic activities(up to 7.24×10^(6) and 9.04×10^(6)g·mol Ni^(-1)·h^(-1), respectively), and produced high-molecular-weight polyethylene(Mw up to 545.7 k Da). Complex Ni3 exhibited high activities for ethylene polymerization at the level of 10^(6) g·mol Ni^(-1)·h^(-1) across a wide range from 30 ℃ to 120 ℃, exhibiting excellent high temperature tolerance. These nickel complexes were also effectively employed in the Copolymerization of ethylene with methyl acrylate, ethyl acrylate, butyl acrylate and lauryl acrylate, producing copolymers with high molecular weights(Mw up to 80.5 k Da) and high polar monomer incorporation(up to 8.2 mol%). Microstructure analyses revealed that the introduction of large sterically hindered substituents facilitated the incorporation of polar functional units into the polymer backbone. This study demonstrates the potential of these nickel-based catalysts for efficient Copolymerization of olefin with polar monomers.

关键词： Neutral nickel catalyst Ethylene polymerization Copolymerization Polar acrylate monomers

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Alternating Copolymerization of CO_(2) and cyclohexene oxide initiated by rare-earth metal complexes stabilized by o-phenylenediamine-bridged tris(phenolate)ligand

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Journal of Rare Earths 2022年第9期40卷 1471-1479,I0005页

作者： Quanyou Yao Yongjie Chen Yaorong Wang Dan Yuan Hongpeng You Yingming Yao Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials ScienceDushu Lake CampusSoochow UniversitySuzhou 215123China State Key Laboratory of Rare-Earth Resource Utilization Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China

A series of o-phenylenediamine bridged tris(phenolate)ligand-stabilized rare-earth metal complexes were synthesized and characterized.Lanthanum(complex 1),neodymium(complex 2^(tBu)),and yttrium(complex 3)complexes stabilized by ligand of buiky tert-butyl substituents are mononuclear,whereas neodymium complexes 2^(Me)and 2^(C1)bearing smaller methyl and chloro substituents are dinuclear,respectively.They were applied in the alternating Copolymerization of CO_(2)and cyclohexene oxide.The addition of benzyl alcohol is beneficial to improving yields(up to 86%)and selectivity of poly(carbonate)(up to 99%).Stoichiometric reaction of benzyl alcohol with rare-earth metal complexes 1 and 2^(tBu)results in formation of complexes 4 and 5 as dinuclear complexes with benzyl alcohol coordination,which was confirmed via single crystal X-ray diffraction analysis,and nuclear magnetic resonance(NMR)spectroscopy(for 4).Complex 5 shows equally good activity and selectivity of that of complex 2^(tBu)and benzyl alcohol,consolidating that complex 5 is indeed generated during polymerization.The neodymium tris(phenolate)5 is one of the few examples of rare-earth metal complex as a single-component initiator for Copolymerization of epoxide and CO_(2).Matrix-assisted laser desorption ionization-time of flight(MALDI-TOF)mass spectrometry analysis proves benzyloxy group as the chain end.^(1)H NMR monitoring suggests that the insertion of CO_(2)may be the first step in the growth of the polymer chain.

关键词： Rare earths CO_(2) Copolymerization Polycarbonate Single-component initiator

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Efficient Copolymerization of Ethylene with Polar Divinyl Monomer by Phosphino-Phenolate Nickel Catalyst

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Chinese Journal of Chemistry 2023年第9期41卷 1037-1044页

作者： Fei Wang Xu-ling Wang Li Pan Bin Wang Yue-Sheng Li Tianjin Key Lab of Composite&Functional Materials School of Material Science and EngineeringTianjin UniversityTianjin 300072China College of Chemistry and Chemical Engineering Yantai UniversityYantaiShandong 264005China

Direct Copolymerization of olefin with polar monomers via a coordination-insertion mechanism appears as the most efficient and at-tractive method to prepare functionalized polyolefins.Herein,we carried out direct Copolymerization of ethylene and allyl acrylate by a bulky phosphino-phenolate nickel catalyst,in which high-molecular-weight copolymers bearing polar five-membered and six-membered ring structures were afforded.Comprehensive NMR and FT-I R analyses revealed multiplex structure of the obtained copolymers,in which both the noncyclic structural units bearing pendant allyl moiety(A)as well as acrylate moiety(B)and the cyclic structural units,y-butyrolactones(C)andδ-valerolactone(D)were found.Exhilaratingly,the content of different structural units of the produced copolymer could be tuned by adjusting the concentration of the comonomer.Moreover,we also proved that the nick-el-based catalyst could produce related copolymers with significantly enhanced copolymer molecular weights in the copolymeriza-tion of allyl acrylate and ethylene compared with the palladium-based catalyst under the same conditions.

关键词： Coordination and insertion Copolymerization Nickel Polar monomer Polyolefin

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Oxygen/Sulfur Atom Exchange Copolymerization of Carbon Disulfide and Propylene Oxide by a Highly Effective Heterogeneous Berlin Green Catalyst

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Chemical Research in Chinese Universities 2023年第5期39卷 790-796页

作者： Munir Ullah KHAN Safir Ullah KHAN CAO Xiaohan Muhammad USMAN Muhammad Naeem SHAH Abdul GHAFFAR Muhammad HASSAN ZHANG Chengjian ZHANG Xinghong State Key Laboratory of Motor Vehicle Biofuel Technology International Research Center for X PolymersDepartment of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027P.R.China Shanxi-Zheda Institute of Advanced Materials and Chemical Engineering Shanxi 030013P.R.China Hefei National Laboratory for Physical Science at the Microscale School of Life SciencesUniversity of Science and Technology of ChinaHefei 230027P.R.China Key Laboratory of Macromolecular Synthesis and Functionalization(Ministry of Education) International Research Center for X PolymersDepartment of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027P.R.China College of Information Science and Electronic Engineering Zhejiang UniversityHangzhou 310027P.R.China Advanced Materials Research Center Zhejiang University-University of Illinois at Urbana-Champaign Institute(ZJU-UIUC)Haining 314400P.R.China

In this study,we report that Berlin Green(FeFe-BG)framework exhibits superior performance in the catalytic coupling of carbon disulfide(CS_(2))and propylene oxide(PO)to generate a random copolymer containing thioether,propylene monothiocarbonate and ether units.Oxygen and sulfur atom exchange was detected in polymeric and cyclic thiocarbonate byproducts and utilized to modulate the Copolymerization of CS_(2)and propylene oxide.The coupling of PO and CS_(2)was selective for copolymer formation under various reaction conditions.^(1)H and^(13)C NMR spectroscopy determined two distinct polymer linkages and two cyclic byproducts.Copolymer number average molecular weights ranged from 6.4 kg/mol to 10.5 kg/mol,with a comparatively low polydispersity of 1.3-1.7.The CS_(2)/PO molar feed ratio had a significant impact on the O/S exchange process;the ratio of cyclic thiocarbonate byproducts could be efficiently regulated by tuning the CS_(2)molar feed ratio.

关键词： Carbon disulfide Copolymerization Prussian Blue analogue Heterogeneous catalysis Berlin Green

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Implementing an“Impracticable”Copolymerization to Fabricate a Desired Polymer Precursor for N-doped Porous Carbons

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Engineering 2022年第9期16卷 154-161页

作者： Shi-Chao Qi Xiao-Jie Lu Yin-Cong Lou Rui Zhou Ding-Ming Xue Xiao-Qin Liu Lin-Bing Sun State Key Laboratory of Materials-Oriented Chemical Engineering Jiangsu National Synergetic Innovation Center for Advanced Material(SICAM)College of Chemical EngineeringNanjing Tech UniversityNanjing 211816China

It is common that a proof-of-concept of a desired reaction,which might generate materials with new functions or application potential,is eventually proved impracticable or commercially unfeasible.Considerable efforts have been made but wasted in searching for unknown reaction conditions in solvent environments because it was believed that the activity of reactants can be enhanced to facilitate reactions by dissolving them in solvents.However,an abnormal case was discovered in this study.A desired Copolymerization reaction between 1,3,5-tris(chloromethyl)-2,4,6-trimethylbenzene and melamine was confirmed to be impracticable under various solvent conditions;however,it was successfully implemented using a solvent-free method.Using first-principle calculations and molecular dynamics simulations,two decisive factors that the reaction in solvents cannot possess,namely the reaction equilibrium being pushed by the timely release of by-products and the confined thermal motions of the activated monomer molecules in the solid phase,were demonstrated to make the Copolymerization successful in the solvent-free method.Owing to the high aromaticity and azacyclo-content,the as-synthetic copolymer exhibited good application potential as a precursor to fabricate N-doped porous carbons with satisfactory carbon yields,ideal N contents,desired textural properties,and competitive CO_(2)capture abilities compared to other representative counterparts reported recently.

关键词： Solvent-free method Solvent effect Copolymerization N-doped porous carbon

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Recyclable polymer functionalization via end-group modification and block/random Copolymerization

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Green Energy & Environment 2021年第4期6卷 578-584页

作者： Yihuan Liu Jiaqi Wu Huan Liang Zhao Jin Lianzhu Sheng Xin Hu Ning Zhu Kai Guo College of Biotechnology and Pharmaceutical Engineering Nanjing Tech UniversityNanjingJiangsu 211800China College of Materials Science and Engineering Nanjing Tech UniversityNanjingJiangsu 211800China State Key Laboratory of Materials-Oriented Chemical Engineering Nanjing Tech UniversityNanjingJiangsu 211800China

Recyclable polymers offer a great opportunity to address the environmental issues of plastics.Herein,functionalization of recyclable polymers,poly((R)-3,4-trans six-membered ring-fused GBL)(P((R)-M)),were reported via end-group modifications and block/random Copolymerizations.Di-n-butylmagnesium was selected to catalyze ring-opening polymerization(ROP)of(R)-M in the presence of a series of functional alcohols as the initiators.Block/random Copolymerizations of(R)-M andε-caprolactone(ε-CL),L-lactide(L-LA)and trimethylene carbonate(TMC)were performed to control the onset decomposition temperature(T_(d)),melting temperature(T_(m))and glass transition temperature(T_(g)).These functionalized recyclable polymers would find broad applications as the sustainable plastics.

关键词： Recyclable polymers End-group modification Copolymerization Ring-opening polymerization

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The Effect of Oxygen to Salen-Co Complexes for the Copolymerization of PO/C02

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Chinese Journal of Polymer Science 2020年第10期38卷 1124-1130,I0007页

作者： Ran-Long Duan Yan-Chuan Zhou Zhi-Qiang Sun Yue-Zhou Huang Xuan Pang Xue-Si Chen Key Llaboratory ofPolymer Eomaterials ChangchunIntitute of Apied ChemistyChinese Academy ofSciencesChangchun 130022 China University of Science and Technology of China Hefei 230026 China

A series of Salen-Co(Ⅱ)complexes were synthesized to study the effect of O2 on the catalytic performance of Salen-Co complexes for the Copolymerization of PO/CO2 The Salen-Co(Ⅱ) complexes showed low activity on the cyclo addition of CO2 to PO with the aid of a cocatalyst such as PPNCI Unexpectedly,with the addition of O2 the activity of Salen-C(Ⅱ)complexes was obviously increased and 100%cylic carbonate was obtained.As the pressure of O2 increased,the activity of the complex also increased.With the existence of 02 the activity of the complexes was influenced by their structures and the pressure of 02,and the camplexes with the conjugated structure showed higher activity.The structures of cocatalyst also played a crucial role as for the change of the activity By altering the electrophilit of Salen-Co(Ⅲ),O2 can also be used as cocatalyst for the Copolymerization of PO/CO2。

关键词： Salen-cobalt Epoxides Carbon dioxide Copolymerization

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Mechanism-inspired Design of Heterodinuclear Catalysts for Copolymerization of Epoxide and Lactone

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Chinese Journal of Polymer Science 2020年第9期38卷 950-957,I0006页

作者： Wei-Min Ren Rui-Jing Wang Bai-Hao Ren Ge-Ge Gu Tian-Jun Yue State Key Laboratory of Fine Chemicals Dalian University of TechnologyDalian 116024China

Polyesters,as a class of high-performance and versatile polymer materials,often suffer from some drawbacks,such as hydrophobicity and brittleness due to their single structure nature.Thus,modifications have attracted much attention for enhancing their desirable properties,of which one efficient way is incorporating the aliphatic polyether segment into the main chain of the polyester.However,this approach is of much challenge because the obtained polyesters are problematic in either low alternating degree or low molecular weight.Herein,we describe an efficient strategy to incorporate polyether fragment into polyester by developing a novel Co-Al based heterodinuclear complex for mediating the Copolymerization of propylene oxide(PO)withε-caprolactone(CL).The tracking experiments reveal that PO and CL convert into the polymer chain throughout the polymerization process.Especially,the linear increase in the molecular weight with conversion of CL indicates the controllable nature of the Copolymerization.The competition polymerization,offering the monomer reactivity ratios of rCL=0.96 and rPO=1.04,suggests that the tendency of self-propagation or incorporation of monomers is nearly identical.interestingly,the obtained polymers with different ether contents exhibit tunable thermal properties with enhanced decomposition temperature for the polymer with higher ether content.The newly developed heterodinuclear complex for new polymerization provides an idea to synthesize new functional polymeric materials.

关键词： Heterodinuclear catalysis Polyester-polyether copolymer Lactone Epoxide Copolymerization

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

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Chinese Journal of Polymer Science 2020年第9期38卷 941-949,I0005页

作者： Yan-Qing Li Jian Zhou Ru Xiao Zheng-Guo Cai State Key Laboratory for Modification of Chemical Fibers and Polymer Materials College of Material Science and EngineeringDonghua UniversityShanghai 201620China College of Biological and Chemical Engineering Guangxi University of Science and TechnologyLiuzhou 545006China

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 CI 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).

关键词： Imidazolidin-2-imine ligand Nickel complex Norbornene para-Chlorostyrene Copolymerization

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Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene(EDOT): Improved Electrochemical Performance for Electrochromic Device Applications

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Chinese Journal of Polymer Science 2020年第2期38卷 109-117,I0004页

作者： Serife O.Hacioglu Iskenderun Technical University Department of Engineering Science

In this study,novel electrochromic copolymers of 3,4-ethylenedioxythiophene(EDOT)and(E)-1,2-bis(2-fluoro-4-(4-hexylthiophen-2-yl)phenyl)diazene(M1)with different monomer feed ratios were designed and synthesized electrochemically.Electrochemical and spectroelectrochemical characterizations were performed using voltammetry and UV-Vis-NIR spectrophotometry techniques to test the applicability of copolymers for electrochromic applications.In terms of electrochemical behaviors,addition of an electron-rich EDOT unit into the azobenzenecontaining copolymer increased the electron density on the polymer chain and afforded copolymers with very low oxidation potentials at around0.30 V.While the homopolymers(P1 and PEDOT)exhibited neutral state absorptions centered at 510 and 583 nm,EDOT-bearing copolymers showed red shifted absorptions compared to those of P1 with narrower optical band gaps.In addition,the poor optical contrast and switching times of azobenzene-bearing homopolymer were significantly improved with EDOT addition into the copolymer chain.As a result of the promising electrochromic and kinetic preperties,Co P1.5-bearing single layer electrochromic device that works between purple and light greenish blue colors was constructed and characterized.

关键词： Azobenzene EDOT Copolymerization Electrochromic device

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