沸石咪唑酯骨架-67高效催化L-丙交酯的开环聚合反应
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摘要
为了探究沸石咪唑酯骨架材料(Zeolitic Imidazolate Frameworks,ZIFs)结构中的金属单元对其催化活性的影响,我们采用室温法合成了ZIF-8、Zn/Co-ZIF和ZIF-67,并用其催化L-丙交酯的本体开环聚合反应。在相同的反应条件下,ZIF-67具有最高的催化活性。与2-甲基咪唑(配体)作为催化剂相比,ZIF-67催化得到的聚乳酸具有高度全同立构结构。此外,基质辅助激光解吸-飞行时间(MALDI-TOF)质谱表明,ZIF-67催化得到的聚乳酸主要为线状结构。经过3次循环反应后,ZIF-67的催化活性没有明显降低。
To explore the metal effecting in structure of zeolitic imidazolate frameworks( ZIFs) influenced to its catalytic activity,we have synthesized ZIF-8,Zn/Co-ZIF and ZIF-67 by room temperature method and applied them as catalysts for the bulk ring-opening polymerization of L-lactide. Under the same reaction condition,ZIF-67 shows the highest catalytic activity. Compared to 2-methylimidazolate( linker) as a catalyst under the same reaction condition,the poly( lactic acid) obtained with ZIF-67 has highly isotactic structure.In addition,the matrix assisted laser desorption ionization-time of flight( MALDI-TOF) mass spectrum indicate that the poly( lactic acid) obtained with ZIF-67 has an almost linear structure. ZIF-67 can be reused for three times without significantly loss of catalytic activity.
To explore the metal effecting in structure of zeolitic imidazolate frameworks( ZIFs) influenced to its catalytic activity,we have synthesized ZIF-8,Zn/Co-ZIF and ZIF-67 by room temperature method and applied them as catalysts for the bulk ring-opening polymerization of L-lactide. Under the same reaction condition,ZIF-67 shows the highest catalytic activity. Compared to 2-methylimidazolate( linker) as a catalyst under the same reaction condition,the poly( lactic acid) obtained with ZIF-67 has highly isotactic structure.In addition,the matrix assisted laser desorption ionization-time of flight( MALDI-TOF) mass spectrum indicate that the poly( lactic acid) obtained with ZIF-67 has an almost linear structure. ZIF-67 can be reused for three times without significantly loss of catalytic activity.
引文
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[5] Dechy-Cabaret O,Martin-Vaca B,Bourissou D. Controlled Ring-Opening Polymerization of Lactide and Glycolide[J].Chem Rev,2004,104(12):6147-6176.
[6]Kricheldorf H R. Synthesis and Application of Polylactide[J]. Chemosphere,2001,43(1):49-54.
[7]Platel R H,Hodgson L M,Williams C K. Biocompatible Initiators for Lactide Polymerization[J]. Polym Rev,2008,48(1):11-63.
[8]Tschan M J L,Brule E,Haquette P,et al. Synthesis of Biodegradable Polymer from Renewable Resource[J]. Polym Chem,2012,3(4):836-851.
[9]Achmad F,Yamanishi K,Liu Z Y,et al. The Effect of the Impurities in Refinery Process from Fermentation Broth on Lactic Acid Polymerization[J]. J Chem Eng Jpn,2009,42(8):632-635.
[10]Abdel-Fattah T M,Pinnavaia T J. Tin-Substituted Mesoporous Silica Molecular Sieve(Sn-HMS):Synthesis and Properties as a Heterogeneous Catalyst for Lactide Ring-Opening Polymerization[J]. Chem Commun,1996,(5):665-666.
[11]Yu K,Jones C W. Elucidating the Role of Silica Surfaces in the Ring-Opening Polymerization of Lactide:Catalytic Behavior of Silica-Immobilized Zincβ-Diiminate Complexes[J]. J Catal,2004,222(2):558-564.
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[13]Kim E,Shin E W,Yoo I K,et al. Characteristics of Heterogeneous Titanium Alkoxide Catalysts for Ring-Opening Polymerization of Lactide to Produce Polylactide[J]. J Mol Catal A:Chem,2009,298(1/2):36-39.
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[15]Jones M D,Keir C G,Johnson A L,et al. Crystallographic Characterization of Novel Zn(Ⅱ)Silsesquioxane Complexes and Their Application as Initiators for the Production of Polylactide[J]. Polyhedron,2010,29(1):312-316.
[16]Di Iulio C,Jones M D,Mahon M F,et al. Zinc(Ⅱ)Silsesquioxane Complexes and Their Application for the Ring-Opening Polymerization of rac-Lactide[J]. Inorg Chem,2010,49(22):10232-10234.
[17]Di Iulio C,Jones M D,Mahon M F. Synthesis of Al(Ⅲ)Silsesquioxane Complexes and Their Exploitation for the Ring Opening Polymerization of rac-Lactide[J]. J Organomet Chem,2012,718:96-100.
[18]Wanna N,Kraithong T,Khamnaen T,et al. Aluminum-and Calcium-Incorporated MCM-41-Type Silica as Supports for the Immobilization of Titanium(Ⅳ)Isopropoxide in Ring-Opening Polymerization of L-Lactide andε-Caprolactone[J]. Catal Commun,2014,45:118-123.
[19]Lee E J,Lee K M,Jang J,et al. Characteristics of Silica-Supported Tin(Ⅱ)Methoxide Catalysts for Ring-Opening Polymerization(ROP)of L-Lactide[J]. J Mol Catal A:Chem,2014,385:68-72.
[20]Chaemchuen S,Kabir N A,Zhou K,et al. Metal-Organic Frameworks for Upgrading Biogas via CO2Adsorption to Biogas Green Energy[J]. Chem Soc Rev,2013,42(24):9304-9332.
[21]XIAO Fan,CUI Yuanjing,QIAN Guodong. Metal-Organic Frameworks for Fluorescence Detection Applications[J]. Chinese J Appl Chem,2018,35(9):1113-1125(in Chinese).肖帆,崔元靖,钱国栋.金属-有机框架材料的荧光探测应用进展[J].应用化学,2018,35(9):1113-1125.
[22]Chaemchuen S,Luo Z,Zhou K,et al. Defect Formation in Metal-Organic Frameworks Initiated by the Crystal Growth-Rate and Effect on Catalytic Performance[J]. J Catal,2017,354:84-91.
[23]Chughtai A H,Ahmad N,Younns H A,et al. Metal-Organic Frameworks:Versatile Heterogeneous Catalysts for Efficient Catalytic Organic Transformations[J]. Chem Soc Rev,2015,44(19):6804-6849.
[24]Chuck C J,Davidson M G,Jones M D,et al. Air-Stable Titanium Alkoxide Based Metal-Organic Frameworks as an Initiator for Ring-Opening Polymerization of Cyclic Esters[J]. Inorg Chem,2006,45(17):6595-6597.
[25]Wu C Y,Raja D S,Yang C C,et al. Evaluation of Structural Transformation in 2D Metal-Organic Frameworks Based on a4,4'-Sulfonyldibenzoate Linker:Microwave-assisted Solvothermal Synthesis, Characterization and Applications[J].Cryst Eng Comm,2014,16(39):9308-9319.
[26]Luo Z,Chaemchuen S,Zhou K,et al. Influence of Lactic Acid on the Catalytic Performance of MDABCO for Ring-Opening Polymerization of L-Lactide[J]. Appl Catal A:Gen,2017,546:15-21.
[27]Luo Z,Chaemchuen S,Zhou K,et al. Ring-Opening Polymerization of L-Lactide to Cyclic Poly(Lactide)by Zeolitic Imidazole Framework ZIF-8 Catalyst[J]. Chem Sus Chem,2017,10(21):4135-4139.
[28]Phan A,Doonan C J,Uribe-Romo F J,et al. Synthesis,Structure,and Carbon Dioxide Capture Properties of Zeolitic Imidazolate Frameworks[J]. Acc Chem Res,2010,43(1):58-67.
[29]Chen B,Yang Z,Zhu Y,et al. Zeolitic Imidazolate Framework Materials:Recent Progress in Synthesis and Applications[J]. J Mater Chem A,2004,2(40):16811-16831.
[30]Chizallet C,Lazare S,Bazer-Bachi D,et al. Catalysis of Transesterification by a Nonfunctionalized Metal-Organic Framework:Acido-Basicity at the External Surface of ZIF-8 Probed by FTIR and Ab Initio Calculations[J]. J Am Chem Soc,2010,132(35):12365-12377.
[31]Tran U P N,Le K K A,Phan N T S. Expanding Applications of Metal-Organic Frameworks:Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction[J]. ACS Catal,2011,1(2):120-127.
[32]Kalidindi S B,Esken D,Fischer R A. B-N Chemistry@ZIF-8:Dehydrocoupling of Dimethylamine Borane at Room Temperature by Size-Confinement Effects[J]. Chem Eur J,2011,17(24):6594-6597.
[33]Mousavi B,Chaemchuen S,Moosavi B,et al. Zeolitic Imidazole Framework-67 as an Efficient Heterogeneous Catalyst for the Conversion of CO2to Cyclic Carbonates[J]. New J Chem,2016,40(6):5170-5176.
[34]Lin K Y A,Chang H A. Zeolitic Imidazole Framework-67(ZIF-67)as a Heterogeneous Catalyst to Activate Peroxymonosulfate for Degradation of Rhodamine B in Water[J]. J Taiwan Inst Chem Eng,2015,53:40-45.
[35]Coulembier O,Meyer F,Dubois P. Controlled Room Temperature ROP of L-Lactide by ICl3:A Simple Halogen-Bonding Catalyst[J]. Polym Chem,2010,1(4):434-437.
[36]Pietrangelo A,Hillmyer M A,Tolman W B. Stereoselective and Controlled Polymerization of DL-Lactide Using Indium(Ⅲ)Trichloride[J]. Chem Commun,2009,(19):2736-2737.
[37]Pietrangelo A,Knight S C,Gupta A K,et al. Mechanistic Study of the Stereoselective Polymerization of D,L-Lactide Using Indium(Ⅲ)Halides[J]. J Am Chem Soc,2010,132(33):11649-11657.
[38]Kricheldorf H R,Lomadze N,Schwarz G. Cyclic Polylactides by Imidazole-Catalyzed Polymerization of L-Lactide[J].Macromolecules,2008,41(21):7812-7816.
[39]Blakey I,Yu A,Howdle S M,et al. Controlled Polymerization of Lactide Using an Organo-Catalyst in Supercritical Carbon Dioxide[J]. Green Chem,2011,13(8):2032-2037.
[40]Coulembier O,Josse T,Guillerm B,et al. An Imidazole-Based Organocatalyst Designed for Bulk Polymerization of Lactide Isomers:Inspiration from Nature[J]. Chem Commun,2012,48(95):11695-11697.
[41]Nederberg F,Connor E F,Moeller M,et al. New Paradigms for Organic Catalysts:The First Organocatalytic Living Polymerization[J]. Angew Chem Int Ed,2001,40(14):2712-2715.
[42]Chizallet C,Bats N. External Surface of Zeolite Imidazolate Frameworks Viewed Ab Initio:Multifunctionality at the Organic-Inorganic Interface[J]. J Phys Chem Lett,2010,1(1):349-353.
[43]Kuruppathparambil R R,Babu R,Jeong H M,et al. A Solid Solution Zeolitic Imidazolate Framework as a Room Temperature Efficient Catalyst for the Chemical Fixation of CO2[J]. Green Chem,2016,18(23):6349-6356.
[44]Zhou K,Mousavi B,Luo Z,et al. Characterization and Properties of Zn/Co Zeolitic Imidazolate Frameworks vs. ZIF-8 and ZIF-67[J]. J Mater Chem A,2017,5(3):952-957.
[45]Chen Y Z,Wang C,Wu Z Y,et al. From Bimetallic Metal-Organic Framework to Porous Carbon:High Surface Area and Multicomponent Active Dopants for Excellent Electrocatalysis[J]. Adv Mater,2015,27(34):5010-5016.
[46]Kowalski A,Duda A,Penczek S. Polymerization of L,L-Lactide Initiated by Aluminum Isopropoxide Trimer or Tetramer[J]. Macromolecules,1998,31(7):2114-2122.
[47]Katiyar V,Nanavati H. Ring-Opening Polymerization of L-Lactide Using N-Heterocyclic Molecules:Mechanistic,Kinetics and DFT Studies[J]. Polym Chem,2010,1(9):1491-1500.
[48]Frediani M,Semeril D,Mariotti A,et al. Ring Opening Polymerization of Lactide Under Solvent-Free Conditions Catalyzed by a Chlorotitanium Calix[4]arene Complex[J]. Macromol Rapid Commun,2008,29(18):1554-1560.
[49]Zhang M,Ni X,Shen Z. Synthesis of Bimetallic Bis(phenolate)N-Heterocyclic Carbene Lanthanide Complexes and Their Applications in the Ring-Opening Polymerization of L-Lactide[J]. Organometallics,2014,33(23):6861-6867.
[2]Lim L T,Auras R,Rubino M. Processing Technologies for Poly(Lactic Acid)[J]. Prog Polym Sci,2008,33(8):820-852.
[3]Van Wouwe P,Dusselier M,Vanleeuw E,et al. Lactide Synthesis and Chirality Control for Polylactic Acid Production[J].Chem Sus Chem,2016,9(9):907-921.
[4]Terrade F G,Van Krieken J,Verkuijl B J V,et al. Catalytic Cracking of Lactide and Poly(Lactic acid)to Acrylic Acid at Low Temperatures[J]. Chem Sus Chem,2017,10(9):1904-1908.
[5] Dechy-Cabaret O,Martin-Vaca B,Bourissou D. Controlled Ring-Opening Polymerization of Lactide and Glycolide[J].Chem Rev,2004,104(12):6147-6176.
[6]Kricheldorf H R. Synthesis and Application of Polylactide[J]. Chemosphere,2001,43(1):49-54.
[7]Platel R H,Hodgson L M,Williams C K. Biocompatible Initiators for Lactide Polymerization[J]. Polym Rev,2008,48(1):11-63.
[8]Tschan M J L,Brule E,Haquette P,et al. Synthesis of Biodegradable Polymer from Renewable Resource[J]. Polym Chem,2012,3(4):836-851.
[9]Achmad F,Yamanishi K,Liu Z Y,et al. The Effect of the Impurities in Refinery Process from Fermentation Broth on Lactic Acid Polymerization[J]. J Chem Eng Jpn,2009,42(8):632-635.
[10]Abdel-Fattah T M,Pinnavaia T J. Tin-Substituted Mesoporous Silica Molecular Sieve(Sn-HMS):Synthesis and Properties as a Heterogeneous Catalyst for Lactide Ring-Opening Polymerization[J]. Chem Commun,1996,(5):665-666.
[11]Yu K,Jones C W. Elucidating the Role of Silica Surfaces in the Ring-Opening Polymerization of Lactide:Catalytic Behavior of Silica-Immobilized Zincβ-Diiminate Complexes[J]. J Catal,2004,222(2):558-564.
[12]Jones M D,Davidson M G,Keir C G,et al. Heterogeneous Catalysts for the Controlled Ring-Opening Polymerization of rac-Lactide and Homogeneous Silsesquioxane Model Complexes[J]. Dalton Trans,2008,(28):3655-3657.
[13]Kim E,Shin E W,Yoo I K,et al. Characteristics of Heterogeneous Titanium Alkoxide Catalysts for Ring-Opening Polymerization of Lactide to Produce Polylactide[J]. J Mol Catal A:Chem,2009,298(1/2):36-39.
[14]Jones M D,Davidson M G,Keir C G,et al. Zinc(Ⅱ)Homogeneous and Heterogeneous Species and Their Application for the Ring-Opening Polymerization of rac-Lactide[J]. Eur J Inorg Chem,2009,(5):635-642.
[15]Jones M D,Keir C G,Johnson A L,et al. Crystallographic Characterization of Novel Zn(Ⅱ)Silsesquioxane Complexes and Their Application as Initiators for the Production of Polylactide[J]. Polyhedron,2010,29(1):312-316.
[16]Di Iulio C,Jones M D,Mahon M F,et al. Zinc(Ⅱ)Silsesquioxane Complexes and Their Application for the Ring-Opening Polymerization of rac-Lactide[J]. Inorg Chem,2010,49(22):10232-10234.
[17]Di Iulio C,Jones M D,Mahon M F. Synthesis of Al(Ⅲ)Silsesquioxane Complexes and Their Exploitation for the Ring Opening Polymerization of rac-Lactide[J]. J Organomet Chem,2012,718:96-100.
[18]Wanna N,Kraithong T,Khamnaen T,et al. Aluminum-and Calcium-Incorporated MCM-41-Type Silica as Supports for the Immobilization of Titanium(Ⅳ)Isopropoxide in Ring-Opening Polymerization of L-Lactide andε-Caprolactone[J]. Catal Commun,2014,45:118-123.
[19]Lee E J,Lee K M,Jang J,et al. Characteristics of Silica-Supported Tin(Ⅱ)Methoxide Catalysts for Ring-Opening Polymerization(ROP)of L-Lactide[J]. J Mol Catal A:Chem,2014,385:68-72.
[20]Chaemchuen S,Kabir N A,Zhou K,et al. Metal-Organic Frameworks for Upgrading Biogas via CO2Adsorption to Biogas Green Energy[J]. Chem Soc Rev,2013,42(24):9304-9332.
[21]XIAO Fan,CUI Yuanjing,QIAN Guodong. Metal-Organic Frameworks for Fluorescence Detection Applications[J]. Chinese J Appl Chem,2018,35(9):1113-1125(in Chinese).肖帆,崔元靖,钱国栋.金属-有机框架材料的荧光探测应用进展[J].应用化学,2018,35(9):1113-1125.
[22]Chaemchuen S,Luo Z,Zhou K,et al. Defect Formation in Metal-Organic Frameworks Initiated by the Crystal Growth-Rate and Effect on Catalytic Performance[J]. J Catal,2017,354:84-91.
[23]Chughtai A H,Ahmad N,Younns H A,et al. Metal-Organic Frameworks:Versatile Heterogeneous Catalysts for Efficient Catalytic Organic Transformations[J]. Chem Soc Rev,2015,44(19):6804-6849.
[24]Chuck C J,Davidson M G,Jones M D,et al. Air-Stable Titanium Alkoxide Based Metal-Organic Frameworks as an Initiator for Ring-Opening Polymerization of Cyclic Esters[J]. Inorg Chem,2006,45(17):6595-6597.
[25]Wu C Y,Raja D S,Yang C C,et al. Evaluation of Structural Transformation in 2D Metal-Organic Frameworks Based on a4,4'-Sulfonyldibenzoate Linker:Microwave-assisted Solvothermal Synthesis, Characterization and Applications[J].Cryst Eng Comm,2014,16(39):9308-9319.
[26]Luo Z,Chaemchuen S,Zhou K,et al. Influence of Lactic Acid on the Catalytic Performance of MDABCO for Ring-Opening Polymerization of L-Lactide[J]. Appl Catal A:Gen,2017,546:15-21.
[27]Luo Z,Chaemchuen S,Zhou K,et al. Ring-Opening Polymerization of L-Lactide to Cyclic Poly(Lactide)by Zeolitic Imidazole Framework ZIF-8 Catalyst[J]. Chem Sus Chem,2017,10(21):4135-4139.
[28]Phan A,Doonan C J,Uribe-Romo F J,et al. Synthesis,Structure,and Carbon Dioxide Capture Properties of Zeolitic Imidazolate Frameworks[J]. Acc Chem Res,2010,43(1):58-67.
[29]Chen B,Yang Z,Zhu Y,et al. Zeolitic Imidazolate Framework Materials:Recent Progress in Synthesis and Applications[J]. J Mater Chem A,2004,2(40):16811-16831.
[30]Chizallet C,Lazare S,Bazer-Bachi D,et al. Catalysis of Transesterification by a Nonfunctionalized Metal-Organic Framework:Acido-Basicity at the External Surface of ZIF-8 Probed by FTIR and Ab Initio Calculations[J]. J Am Chem Soc,2010,132(35):12365-12377.
[31]Tran U P N,Le K K A,Phan N T S. Expanding Applications of Metal-Organic Frameworks:Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction[J]. ACS Catal,2011,1(2):120-127.
[32]Kalidindi S B,Esken D,Fischer R A. B-N Chemistry@ZIF-8:Dehydrocoupling of Dimethylamine Borane at Room Temperature by Size-Confinement Effects[J]. Chem Eur J,2011,17(24):6594-6597.
[33]Mousavi B,Chaemchuen S,Moosavi B,et al. Zeolitic Imidazole Framework-67 as an Efficient Heterogeneous Catalyst for the Conversion of CO2to Cyclic Carbonates[J]. New J Chem,2016,40(6):5170-5176.
[34]Lin K Y A,Chang H A. Zeolitic Imidazole Framework-67(ZIF-67)as a Heterogeneous Catalyst to Activate Peroxymonosulfate for Degradation of Rhodamine B in Water[J]. J Taiwan Inst Chem Eng,2015,53:40-45.
[35]Coulembier O,Meyer F,Dubois P. Controlled Room Temperature ROP of L-Lactide by ICl3:A Simple Halogen-Bonding Catalyst[J]. Polym Chem,2010,1(4):434-437.
[36]Pietrangelo A,Hillmyer M A,Tolman W B. Stereoselective and Controlled Polymerization of DL-Lactide Using Indium(Ⅲ)Trichloride[J]. Chem Commun,2009,(19):2736-2737.
[37]Pietrangelo A,Knight S C,Gupta A K,et al. Mechanistic Study of the Stereoselective Polymerization of D,L-Lactide Using Indium(Ⅲ)Halides[J]. J Am Chem Soc,2010,132(33):11649-11657.
[38]Kricheldorf H R,Lomadze N,Schwarz G. Cyclic Polylactides by Imidazole-Catalyzed Polymerization of L-Lactide[J].Macromolecules,2008,41(21):7812-7816.
[39]Blakey I,Yu A,Howdle S M,et al. Controlled Polymerization of Lactide Using an Organo-Catalyst in Supercritical Carbon Dioxide[J]. Green Chem,2011,13(8):2032-2037.
[40]Coulembier O,Josse T,Guillerm B,et al. An Imidazole-Based Organocatalyst Designed for Bulk Polymerization of Lactide Isomers:Inspiration from Nature[J]. Chem Commun,2012,48(95):11695-11697.
[41]Nederberg F,Connor E F,Moeller M,et al. New Paradigms for Organic Catalysts:The First Organocatalytic Living Polymerization[J]. Angew Chem Int Ed,2001,40(14):2712-2715.
[42]Chizallet C,Bats N. External Surface of Zeolite Imidazolate Frameworks Viewed Ab Initio:Multifunctionality at the Organic-Inorganic Interface[J]. J Phys Chem Lett,2010,1(1):349-353.
[43]Kuruppathparambil R R,Babu R,Jeong H M,et al. A Solid Solution Zeolitic Imidazolate Framework as a Room Temperature Efficient Catalyst for the Chemical Fixation of CO2[J]. Green Chem,2016,18(23):6349-6356.
[44]Zhou K,Mousavi B,Luo Z,et al. Characterization and Properties of Zn/Co Zeolitic Imidazolate Frameworks vs. ZIF-8 and ZIF-67[J]. J Mater Chem A,2017,5(3):952-957.
[45]Chen Y Z,Wang C,Wu Z Y,et al. From Bimetallic Metal-Organic Framework to Porous Carbon:High Surface Area and Multicomponent Active Dopants for Excellent Electrocatalysis[J]. Adv Mater,2015,27(34):5010-5016.
[46]Kowalski A,Duda A,Penczek S. Polymerization of L,L-Lactide Initiated by Aluminum Isopropoxide Trimer or Tetramer[J]. Macromolecules,1998,31(7):2114-2122.
[47]Katiyar V,Nanavati H. Ring-Opening Polymerization of L-Lactide Using N-Heterocyclic Molecules:Mechanistic,Kinetics and DFT Studies[J]. Polym Chem,2010,1(9):1491-1500.
[48]Frediani M,Semeril D,Mariotti A,et al. Ring Opening Polymerization of Lactide Under Solvent-Free Conditions Catalyzed by a Chlorotitanium Calix[4]arene Complex[J]. Macromol Rapid Commun,2008,29(18):1554-1560.
[49]Zhang M,Ni X,Shen Z. Synthesis of Bimetallic Bis(phenolate)N-Heterocyclic Carbene Lanthanide Complexes and Their Applications in the Ring-Opening Polymerization of L-Lactide[J]. Organometallics,2014,33(23):6861-6867.
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