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Ring-Opening Polymerization of Cyclic Esters and Trimethylene Carbonate Catalyzed by Aluminum Half-Salen Complexes

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Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States
E-mail: [email protected]
Cite this: Inorg. Chem. 2011, 50, 14, 6775–6787
Publication Date (Web):June 15, 2011
https://doi.org/10.1021/ic2008057
Copyright © 2011 American Chemical Society
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    Abstract

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    A series of ONO-tridentate Schiff base ligands derived from chiral and achiral amino alcohols and amino acids were synthesized and reacted with AlEt3 to provide dimeric aluminum complexes. These complexes were tested for the ring-opening polymerization (ROP) of rac-lactide at 70 °C in toluene, producing poly(lactide) with up to 82% isotacticity. The most active of these aluminum complexes was chosen to perform ring-opening homopolymerizations of rac-lactide, trimethylene carbonate (TMC), rac-β-butyrolactone (rac-β-BL), δ-valerolactone (δ-VL), and ε-caprolactone (ε-CL). Kinetic parameters were investigated, and each polymerization was found to be first order with respect to monomer concentration. Fractional orders were observed with respect to catalyst concentration, indicating catalyst aggregation during the polymerization processes. Activation parameters were determined for all monomers, with their ΔG⧧ values at 90 °C being in the order rac-lactide ≈ rac-β-BL > δ-VL > TMC ≈ ε-CL. Fineman–Ross and kinetic studies of the copolymerization of rac-lactide and δ-VL both indicate that the rate of rac-lactide enchainment is higher than that of δ-VL, resulting in a tapered copolymer. In addition, single crystals of one of these aluminum complexes were grown in the presence of rac-lactide and characterized using X-ray crystallography. The unit cell contains two lactide monomers, one d- and one l-lactide, adding further proof that polymerization takes place via an enantiomorphic site control mechanism.

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    Tables and CIF files giving crystallographic data for all complexes reported in this study. This material is available free of charge via the Internet at http://pubs.acs.org.

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    5. Yaqin Cui, Jinxing Jiang, Xiaoyang Mao, Jincai Wu. Mononuclear Salen–Sodium Ion Pairs as Catalysts for Isoselective Polymerization of rac-Lactide. Inorganic Chemistry 2019, 58 (1) , 218-227. https://doi.org/10.1021/acs.inorgchem.8b02290
    6. Changda Li, Haitong Tang, Yu Fang, Zhifeng Xiao, Kunyu Wang, Xiang Wu, Helin Niu, Chengfeng Zhu, Hong-cai Zhou. Bottom-Up Assembly of a Highly Efficient Metal–Organic Framework for Cooperative Catalysis. Inorganic Chemistry 2018, 57 (21) , 13912-13919. https://doi.org/10.1021/acs.inorgchem.8b02434
    7. Francisco M. García-Valle, Vanessa Tabernero, Tomás Cuenca, Marta E. G. Mosquera, Jesús Cano, Stefano Milione. Biodegradable PHB from rac-β-Butyrolactone: Highly Controlled ROP Mediated by a Pentacoordinated Aluminum Complex. Organometallics 2018, 37 (6) , 837-840. https://doi.org/10.1021/acs.organomet.7b00843
    8. Chieh-Ling Lee, Ya-Fan Lin, Man-Ting Jiang, Wei-Yi Lu, Jaya Kishore Vandavasi, Li-Fang Wang, Yi-Chun Lai, Michael Y. Chiang, and Hsuan-Ying Chen . Improvement in Aluminum Complexes Bearing Schiff Bases in Ring-Opening Polymerization of ε-Caprolactone: A Five-Membered-Ring System. Organometallics 2017, 36 (10) , 1936-1945. https://doi.org/10.1021/acs.organomet.7b00068
    9. Hsiu-Wei Ou, Kai-Hsuan Lo, Wei-Ting Du, Wei-Yi Lu, Wan-Jung Chuang, Bor-Hunn Huang, Hsuan-Ying Chen, and Chu-Chieh Lin . Synthesis of Sodium Complexes Supported with NNO-Tridentate Schiff Base Ligands and Their Applications in the Ring-Opening Polymerization of l-Lactide. Inorganic Chemistry 2016, 55 (4) , 1423-1432. https://doi.org/10.1021/acs.inorgchem.5b02043
    10. Yangyang Sun, Jiao Xiong, Zhongran Dai, Xiaobo Pan, Ning Tang, and Jincai Wu . Stereoselective Alkali-Metal Catalysts for Highly Isotactic Poly(rac-lactide) Synthesis. Inorganic Chemistry 2016, 55 (1) , 136-143. https://doi.org/10.1021/acs.inorgchem.5b02709
    11. Meng-Chih Chang, Wei-Yi Lu, Heng-Yi Chang, Yi-Chun Lai, Michael Y. Chiang, Hsing-Yin Chen, and Hsuan-Ying Chen . Comparative Study of Aluminum Complexes Bearing N,O- and N,S-Schiff Base in Ring-Opening Polymerization of ε-Caprolactone and l-Lactide. Inorganic Chemistry 2015, 54 (23) , 11292-11298. https://doi.org/10.1021/acs.inorgchem.5b01858
    12. Sittichoke Tabthong, Tanin Nanok, Pattarawut Sumrit, Palangpon Kongsaeree, Samran Prabpai, Pitak Chuawong, and Pimpa Hormnirun . Bis(pyrrolidene) Schiff Base Aluminum Complexes as Isoselective-Biased Initiators for the Controlled Ring-Opening Polymerization of rac-Lactide: Experimental and Theoretical Studies. Macromolecules 2015, 48 (19) , 6846-6861. https://doi.org/10.1021/acs.macromol.5b01381
    13. Weikai Gu, Pengfei Xu, Yaorong Wang, Yingming Yao, Dan Yuan, and Qi Shen . Synthesis and Characterization of Yttrium and Ytterbium Complexes Supported by Salen Ligands and Their Catalytic Properties for rac-Lactide Polymerization. Organometallics 2015, 34 (12) , 2907-2916. https://doi.org/10.1021/acs.organomet.5b00223
    14. Yunqing Zhu, Charles Romain, Valentin Poirier, and Charlotte K. Williams . Influences of a Dizinc Catalyst and Bifunctional Chain Transfer Agents on the Polymer Architecture in the Ring-Opening Polymerization of ε-Caprolactone. Macromolecules 2015, 48 (8) , 2407-2416. https://doi.org/10.1021/acs.macromol.5b00225
    15. J. P. MacDonald M. P. Shaver . Aluminum Salen and Salan Polymerization Catalysts: From Monomer Scope to Macrostructure Control. 2015, 147-167. https://doi.org/10.1021/bk-2015-1192.ch010
    16. Haobing Wang, Yang Yang, and Haiyan Ma . Stereoselectivity Switch between Zinc and Magnesium Initiators in the Polymerization of rac-Lactide: Different Coordination Chemistry, Different Stereocontrol Mechanisms. Macromolecules 2014, 47 (22) , 7750-7764. https://doi.org/10.1021/ma501896r
    17. Joice S. Klitzke, Thierry Roisnel, Evgeny Kirillov, Osvaldo de L. Casagrande, Jr., and Jean-François Carpentier . Discrete O-Lactate and β-Alkoxybutyrate Aluminum Pyridine–Bis(naphtholate) Complexes: Models for Mechanistic Investigations in the Ring-Opening Polymerization of Lactides and β-Lactones. Organometallics 2014, 33 (20) , 5693-5707. https://doi.org/10.1021/om401214q
    18. Charles Romain, Christophe Fliedel, Stéphane Bellemin-Laponnaz, and Samuel Dagorne . NHC Bis-Phenolate Aluminum Chelates: Synthesis, Structure, and Use in Lactide and Trimethylene Carbonate Polymerization. Organometallics 2014, 33 (20) , 5730-5739. https://doi.org/10.1021/om5004557
    19. Nicolas Maudoux, Thierry Roisnel, Jean-François Carpentier, and Yann Sarazin . Aluminum, Indium, and Mixed Yttrium–Lithium Complexes Supported by a Chiral Binap-Based Fluorinated Dialkoxide: Structural Features and Heteroselective ROP of Lactide. Organometallics 2014, 33 (20) , 5740-5748. https://doi.org/10.1021/om500458g
    20. Kimberly M. Osten, Dinesh C. Aluthge, Brian O. Patrick, and Parisa Mehrkhodavandi . Probing the Role of Secondary versus Tertiary Amine Donor Ligands for Indium Catalysts in Lactide Polymerization. Inorganic Chemistry 2014, 53 (18) , 9897-9906. https://doi.org/10.1021/ic501529f
    21. Ayellet Stopper, Konstantin Press, Jun Okuda, Israel Goldberg, and Moshe Kol . Zirconium Complexes of Phenylene-Bridged {ONSO} Ligands: Coordination Chemistry and Stereoselective Polymerization of rac-Lactide. Inorganic Chemistry 2014, 53 (17) , 9140-9150. https://doi.org/10.1021/ic501164c
    22. Joice S. Klitzke, Thierry Roisnel, Evgeny Kirillov, Osvaldo de L. Casagrande, Jr., and Jean-François Carpentier . Yttrium– and Aluminum–Bis(phenolate)pyridine Complexes: Catalysts and Model Compounds of the Intermediates for the Stereoselective Ring-Opening Polymerization of Racemic Lactide and β-Butyrolactone. Organometallics 2014, 33 (1) , 309-321. https://doi.org/10.1021/om401047r
    23. Solomon H. Reisberg, Harry J. Hurley, Robert T. Mathers, Joseph M. Tanski, and Yutan D. Y. L. Getzler . Lactide Cyclopolymerization Kinetics, X-ray Structure, and Solution Dynamics of (tBu-SalAmEE)Al and a Cautionary Tale Of Polymetalate Formation. Macromolecules 2013, 46 (9) , 3273-3279. https://doi.org/10.1021/ma400046x
    24. Mickael Normand, Vincent Dorcet, Evgeny Kirillov, and Jean-François Carpentier . {Phenoxy-imine}aluminum versus -indium Complexes for the Immortal ROP of Lactide: Different Stereocontrol, Different Mechanisms. Organometallics 2013, 32 (6) , 1694-1709. https://doi.org/10.1021/om301155m
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    27. Nduka Ikpo, Stephanie M. Barbon, Marcus W. Drover, Louise N. Dawe, and Francesca M. Kerton . Aluminum Methyl and Chloro Complexes Bearing Monoanionic Aminephenolate Ligands: Synthesis, Characterization, and Use in Polymerizations. Organometallics 2012, 31 (23) , 8145-8158. https://doi.org/10.1021/om300757u
    28. Insun Yu, Alberto Acosta-Ramírez, and Parisa Mehrkhodavandi . Mechanism of Living Lactide Polymerization by Dinuclear Indium Catalysts and Its Impact on Isoselectivity. Journal of the American Chemical Society 2012, 134 (30) , 12758-12773. https://doi.org/10.1021/ja3048046
    29. Courtney C. Roberts, Brandon R. Barnett, David B. Green, and Joseph M. Fritsch . Synthesis and Structures of Tridentate Ketoiminate Zinc Complexes That Act As l-Lactide Ring-Opening Polymerization Catalysts. Organometallics 2012, 31 (11) , 4133-4141. https://doi.org/10.1021/om200865w
    30. Hsiao-Li Chen, Saikat Dutta, Pei-Ying Huang, and Chu-Chieh Lin . Preparation and Characterization of Aluminum Alkoxides Coordinated on salen-Type Ligands: Highly Stereoselective Ring-Opening Polymerization of rac-Lactide. Organometallics 2012, 31 (5) , 2016-2025. https://doi.org/10.1021/om201281w
    31. Mickael Normand, Evgeny Kirillov, Thierry Roisnel, and Jean-François Carpentier . Indium Complexes of Fluorinated Dialkoxy-Diimino Salen-like Ligands for Ring-Opening Polymerization of rac-Lactide: How Does Indium Compare to Aluminum?. Organometallics 2012, 31 (4) , 1448-1457. https://doi.org/10.1021/om200906e
    32. Miloud Bouyahyi, Thierry Roisnel, and Jean-François Carpentier . Aluminum Complexes of Bidentate Fluorinated Alkoxy-Imino Ligands: Syntheses, Structures, and Use in Ring-Opening Polymerization of Cyclic Esters. Organometallics 2012, 31 (4) , 1458-1466. https://doi.org/10.1021/om200907x
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    35. Jan Podhorsky, Michal Babiak, Jiri Pinkas, Corinna Hegemann, Sanjay Mathur, Zdenek Moravec. New mixed-ligand organoaluminum heteroarylalkenolates. Polyhedron 2021, 194 , 114953. https://doi.org/10.1016/j.poly.2020.114953
    36. Xiao Wu, Katie J. Lamb, Agustín Lara-Sánchez, Carlos Alonso-Moreno, Michael North, José A. Castro-Osma. Homogeneous aluminum and iron catalysts for the synthesis of organic molecules and biodegradable polymers. 2021, 3-43. https://doi.org/10.1016/B978-0-12-818429-5.00002-8
    37. Kwanchanok Udomsasporn, Setsiri Haesuwannakij, Parichat Piromjitpong, Phongnarin Chumsaeng, Khamphee Phomphrai. Comparative bindings of lactones, lactide, and cyclic carbonates: experimental insights into the coordination step of polymerization. Dalton Transactions 2020, 49 (41) , 14378-14382. https://doi.org/10.1039/D0DT03323E
    38. Xiaofeng Yu, Cheng Zhang, Zhongxia Wang. Controlled Polymerization of ϵ‐Caprolactone using Aluminum and Zinc Complexes with Iminophosphorane Ligands. ChemistrySelect 2020, 5 (1) , 426-429. https://doi.org/10.1002/slct.201904185
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    43. Ting-Wei Huang, Rou-Rong Su, Yi-Chen Lin, Hsin-Yu Lai, Chien-Yi Yang, Gopal Chandru Senadi, Yi-Chun Lai, Michael Y. Chiang, Hsuan-Ying Chen. Improvement in aluminum complexes bearing a Schiff base in ring-opening polymerization of ε-caprolactone: the synergy of the N,S-Schiff base in a five-membered ring aluminum system. Dalton Transactions 2018, 47 (43) , 15565-15573. https://doi.org/10.1039/C8DT03285H
    44. Kirill V. Zaitsev, Valeriy S. Cherepakhin, Alexander Zherebker, Alexey Kononikhin, Eugene Nikolaev, Andrei V. Churakov. Aluminum Complexes Based on Tridentate Amidoalkoxide NNO-Ligands: Synthesis, Structure, and Properties. Journal of Organometallic Chemistry 2018, 875 , 11-23. https://doi.org/10.1016/j.jorganchem.2018.08.021
    45. Fabio A. Vengoechea-Gómez, Miguel-Ángel Velázquez-Carmona, Jorge Barroso, Gabriel Merino, Miguel-Ángel Muñoz-Hernández. Isomerization and luminescent properties of Schiff-base aluminum complexes containing 1H-pyrrole-2-carbaldehyde moieties. Inorganica Chimica Acta 2018, 482 , 535-541. https://doi.org/10.1016/j.ica.2018.06.048
    46. Jiao Xiong, Yangyang Sun, Jitao Jiang, Changjuan Chen, Xiaobo Pan, Cheng Wang, Jincai Wu. Metal-size influence of alkali metal complexes for polymerization of rac-lactide. Polyhedron 2018, 141 , 118-124. https://doi.org/10.1016/j.poly.2017.11.046
    47. Florence Isnard, Mario Carratù, Marina Lamberti, Vincenzo Venditto, Mina Mazzeo. Copolymerization of cyclic esters, epoxides and anhydrides: evidence of the dual role of the monomers in the reaction mixture. Catalysis Science & Technology 2018, 8 (19) , 5034-5043. https://doi.org/10.1039/C8CY01174E
    48. Jean-Marie E. P. Cols, Victoria G. Hill, Stella K. Williams, Ruaraidh D. McIntosh. Aggregated initiators: defining their role in the ROP of rac -lactide. Dalton Transactions 2018, 47 (31) , 10626-10635. https://doi.org/10.1039/C8DT01229F
    49. Tiziana Fuoco, Daniela Pappalardo. Aluminum Alkyl Complexes Bearing Salicylaldiminato Ligands: Versatile Initiators in the Ring-Opening Polymerization of Cyclic Esters. Catalysts 2017, 7 (12) , 64. https://doi.org/10.3390/catal7020064
    50. Iman Taraghi, Sandra Paszkiewicz, Janusz Grebowicz, Abdolhossein Fereidoon, Zbigniew Roslaniec. Nanocomposites of Polymeric Biomaterials Containing Carbonate Groups: An Overview. Macromolecular Materials and Engineering 2017, 302 (10) , 1700042. https://doi.org/10.1002/mame.201700042
    51. Xiu-Yan Dong, Lei Gao, Fei Wang, Yang Zhang, Wen-Kui Dong. Tri- and Mono-Nuclear Zinc(II) Complexes Based on Half- and Mono-Salamo Chelating Ligands. Crystals 2017, 7 (9) , 267. https://doi.org/10.3390/cryst7090267
    52. Danay Osorio Meléndez, José A. Castro-Osma, Agustín Lara-Sánchez, René S. Rojas, Antonio Otero. Ring-opening polymerization and copolymerization of cyclic esters catalyzed by amidinate aluminum complexes. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (14) , 2397-2407. https://doi.org/10.1002/pola.28629
    53. Chiao-Yin Hsu, Hsi-Ching Tseng, Jaya Kishore Vandavasi, Wei-Yi Lu, Li-Fang Wang, Michael Y. Chiang, Yi-Chun Lai, Hsing-Yin Chen, Hsuan-Ying Chen. Investigation of the dinuclear effect of aluminum complexes in the ring-opening polymerization of ε-caprolactone. RSC Advances 2017, 7 (31) , 18851-18860. https://doi.org/10.1039/C7RA02136D
    54. , V.V. Brei, A.M. Varvarin, , S.V. Prudius, . One-pot synthesis of δ-valerolactone from tetrahydrofurfuryl alcohol and δ-valerolactone amidation over Сu/ZnO-Al2O3 catalyst. Himia, Fizika ta Tehnologia Poverhni 2016, 7 (4) , 395-404. https://doi.org/10.15407/hftp07.04.395
    55. Jingwei Yang, Zhiqiang Sun, Ranlong Duan, Lili Li, Xuan Pang, Xuesi Chen. Copolymer of lactide and ε-caprolactone catalyzed by bimetallic Schiff base aluminum complexes. Science China Chemistry 2016, 59 (11) , 1384-1389. https://doi.org/10.1007/s11426-016-0118-9
    56. Yanfei Yu, Dan Yuan, Yaorong Wang, Yingming Yao. Lanthanide alkoxide complexes stabilized by a novel salen-type Schiff-base ligand: Synthesis, structure, and catalysis for the polymerization of lactide. Journal of Organometallic Chemistry 2016, 819 , 37-45. https://doi.org/10.1016/j.jorganchem.2016.06.020
    57. Miao Huang, Haiyan Ma. Magnesium and Zinc Complexes Supported by N,N,O Tridentate Ligands: Synthesis and Catalysis in the Ring‐Opening Polymerization of rac ‐Lactide and α‐Methyltrimethylene Carbonate. European Journal of Inorganic Chemistry 2016, 2016 (23) , 3791-3803. https://doi.org/10.1002/ejic.201600441
    58. Pattarawut Sumrit, Pitak Chuawong, Tanin Nanok, Tanwawan Duangthongyou, Pimpa Hormnirun. Aluminum complexes containing salicylbenzoxazole ligands and their application in the ring-opening polymerization of rac-lactide and ε-caprolactone. Dalton Transactions 2016, 45 (22) , 9250-9266. https://doi.org/10.1039/C6DT00990E
    59. Yen-Tzu Huang, Wei-Chu Wang, Chun-Pin Hsu, Wei-Yi Lu, Wan-Jung Chuang, Michael Y. Chiang, Yi-Chun Lai, Hsuan-Ying Chen. The ring-opening polymerization of ε-caprolactone and l -lactide using aluminum complexes bearing benzothiazole ligands as catalysts. Polymer Chemistry 2016, 7 (26) , 4367-4377. https://doi.org/10.1039/C6PY00569A
    60. Nicolas Maudoux, Eric Tan, Yuya Hu, Thierry Roisnel, Vincent Dorcet, Jean-François Carpentier, Yann Sarazin. Aluminium, gallium and indium complexes supported by a chiral phenolato-prolinolato dianionic ligand. Main Group Metal Chemistry 2016, 39 (5-6) https://doi.org/10.1515/mgmc-2016-0036
    61. Hsing-Yin Chen, Ying-Hsien Lee, Michael Y. Chiang, Wei-Yi Lu, Hsi-Ching Tseng, Hsin-Yi Tsai, Yu-Hsieh Chen, Yi-Chun Lai, Hsuan-Ying Chen. Coordinating effect in ring-opening polymerization of ε-caprolactone using aluminum complexes bearing bisphenolate as catalysts. RSC Advances 2015, 5 (100) , 82018-82026. https://doi.org/10.1039/C5RA10753A
    62. Yi-Liang Hsieh, Ning Huang, Gene-Hsiang Lee, Chi-How Peng. Bipyridine-phenolate based aluminum complexes mediated ring-opening polymerization of ε-caprolactone and lactides with a high stereoselectivity. Polymer 2015, 72 , 281-291. https://doi.org/10.1016/j.polymer.2015.02.026
    63. Alekha Kumar Sutar, Tungabidya Maharana, Anita Routaray, Nibedita Nath. Ring-Opening Polymerization of Lactide. 2015, 193-224. https://doi.org/10.1002/9781118998939.ch6
    64. Thomas R. Forder, Matthew D. Jones. Synthesis and characterisation of aluminium( iii ) imine bis(phenolate) complexes with application for the polymerisation of rac-LA. New Journal of Chemistry 2015, 39 (3) , 1974-1978. https://doi.org/10.1039/C4NJ02228A
    65. Stephanie M. Quan, Paula L. Diaconescu. High activity of an indium alkoxide complex toward ring opening polymerization of cyclic esters. Chemical Communications 2015, 51 (47) , 9643-9646. https://doi.org/10.1039/C5CC01312G
    66. Yu Cui, Weikai Gu, Yaorong Wang, Bei Zhao, Yingming Yao, Qi Shen. Synthesis and characterization of rare-earth metal complexes supported by a new pentadentate Schiff base and their application in heteroselective polymerization of rac-lactide. Catalysis Science & Technology 2015, 5 (6) , 3302-3312. https://doi.org/10.1039/C5CY00322A
    67. Miao Huang, Chen Pan, Haiyan Ma. Ring-opening polymerization of rac-lactide and α-methyltrimethylene carbonate catalyzed by magnesium and zinc complexes derived from binaphthyl-based iminophenolate ligands. Dalton Transactions 2015, 44 (27) , 12420-12431. https://doi.org/10.1039/C5DT00158G
    68. Christophe Fliedel, Vitor Rosa, Filipa M. Alves, Ana. M. Martins, Teresa Avilés, Samuel Dagorne. P,O-Phosphinophenolate zinc( ii ) species: synthesis, structure and use in the ring-opening polymerization (ROP) of lactide, ε-caprolactone and trimethylene carbonate. Dalton Transactions 2015, 44 (27) , 12376-12387. https://doi.org/10.1039/C5DT00458F
    69. Swarup Ghosh, Ravikumar R. Gowda, Rajamony Jagan, Debashis Chakraborty. Gallium and indium complexes containing the bis(imino)phenoxide ligand: synthesis, structural characterization and polymerization studies. Dalton Transactions 2015, 44 (22) , 10410-10422. https://doi.org/10.1039/C5DT00811E
    70. Marina M. Kireenko, Ekaterina A. Kuchuk, Kirill V. Zaitsev, Viktor A. Tafeenko, Yuri F. Oprunenko, Andrei V. Churakov, Elmira Kh. Lermontova, Galina S. Zaitseva, Sergey S. Karlov. Aluminum complexes based on pyridine substituted alcohols: synthesis, structure, and catalytic application in ROP. Dalton Transactions 2015, 44 (26) , 11963-11976. https://doi.org/10.1039/C5DT01001B
    71. Hsi-Ching Tseng, Michael Y. Chiang, Wei-Yi Lu, Yen-Jen Chen, Cheng-Jie Lian, Yu-Hsieh Chen, Hsin-Yi Tsai, Yi-Chun Lai, Hsuan-Ying Chen. A closer look at ε-caprolactone polymerization catalyzed by alkyl aluminum complexes: the effect of induction period on overall catalytic activity. Dalton Transactions 2015, 44 (26) , 11763-11773. https://doi.org/10.1039/C5DT01563D
    72. Yangyang Sun, Yaqin Cui, Jiao Xiong, Zhongran Dai, Ning Tang, Jincai Wu. Different mechanisms at different temperatures for the ring-opening polymerization of lactide catalyzed by binuclear magnesium and zinc alkoxides. Dalton Transactions 2015, 44 (37) , 16383-16391. https://doi.org/10.1039/C5DT01784J
    73. Yu-Hsieh Chen, Yen-Jen Chen, Hsi-Ching Tseng, Cheng-Jie Lian, Hsin-Yi Tsai, Yi-Chun Lai, Sodio C. N. Hsu, Michael Y. Chiang, Hsuan-Ying Chen. Comparing l -lactide and ε-caprolactone polymerization by using aluminum complexes bearing ketiminate ligands: steric, electronic, and chelating effects. RSC Advances 2015, 5 (121) , 100272-100280. https://doi.org/10.1039/C5RA15530D
    74. Hsi-Ching Tseng, Fu-Shen Chen, Michael Y. Chiang, Wei-Yi Lu, Yu-Hsieh Chen, Yi-Chun Lai, Hsuan-Ying Chen. Optimizing ring-opening polymerization of ε-caprolactone by using aluminum complexes bearing amide as catalysts and their application in synthesizing poly-ε-caprolactone with special initiators and other polycycloesters. RSC Advances 2015, 5 (110) , 90682-90690. https://doi.org/10.1039/C5RA21252A
    75. Yangyang Sun, Lei Wang, Dawei Yu, Ning Tang, Jincai Wu. Zinc/magnesium–sodium/lithium heterobimetallic triphenolates: Synthesis, characterization, and application as catalysts in the ring-opening polymerization of l-lactide and CO2/epoxide coupling. Journal of Molecular Catalysis A: Chemical 2014, 393 , 175-181. https://doi.org/10.1016/j.molcata.2014.06.017
    76. Ning Zhao, Qiuwen Wang, Guohua Hou, Haibin Song, Guofu Zi. Synthesis, structure, and catalytic activity of aluminum chloride complexes with chiral biaryl Schiff-base ligands. Inorganic Chemistry Communications 2014, 44 , 86-90. https://doi.org/10.1016/j.inoche.2014.03.009
    77. Ruan Jianming, Xiao Anguo, Wu Hongwei, Yang Hailin. Review – recent development of ring-opening polymerization of cyclic esters using aluminum complexes. Designed Monomers and Polymers 2014, 17 (4) , 345-355. https://doi.org/10.1080/15685551.2013.840509
    78. Nicolas Maudoux, Thierry Roisnel, Vincent Dorcet, Jean-François Carpentier, Yann Sarazin. Chiral (1,2)-Diphenylethylene-Salen Complexes of Triel Metals: Coordination Patterns and Mechanistic Considerations in the Isoselective ROP of Lactide. Chemistry - A European Journal 2014, 20 (20) , 6131-6147. https://doi.org/10.1002/chem.201304788
    79. Ning Zhao, Qiuwen Wang, Guohua Hou, Haibin Song, Guofu Zi. Synthesis, structure, and catalytic activity of organoaluminum complexes with chiral biaryl Schiff-base ligands. Inorganica Chimica Acta 2014, 413 , 128-135. https://doi.org/10.1016/j.ica.2014.01.009
    80. Ning Zhao, Qiuwen Wang, Guohua Hou, Haibin Song, Guofu Zi. Synthesis, structure, and catalytic activity of binuclear aluminum chloride complexes with chiral biaryl-based ligands. Inorganic Chemistry Communications 2014, 41 , 6-10. https://doi.org/10.1016/j.inoche.2013.12.023
    81. Ning Zhao, Qiuwen Wang, Guohua Hou, Haibin Song, Guofu Zi. Synthesis, structure, and catalytic activity of binuclear aluminum complexes with chiral biaryl-based N2O ligands. Journal of Organometallic Chemistry 2014, 754 , 51-58. https://doi.org/10.1016/j.jorganchem.2013.12.035
    82. Ilaria D'Auria, Marina Lamberti, Mina Mazzeo, Stefano Milione, Claudio Pellecchia. Phosphido-diphosphine pincer aluminum complexes as catalysts for ring opening polymerization of cyclic esters. Journal of Polymer Science Part A: Polymer Chemistry 2014, 52 (1) , 49-60. https://doi.org/10.1002/pola.26969
    83. Sittichoke Tabthong, Tanin Nanok, Palangpon Kongsaeree, Samran Prabpai, Pimpa Hormnirun. Monomethylaluminum and dimethylaluminum pyrrolylaldiminates for the ring-opening polymerization of rac-lactide: effects of ligand structure and coordination geometry. Dalton Trans. 2014, 43 (3) , 1348-1359. https://doi.org/10.1039/C3DT52455H
    84. Jakub Wojtaszak, Krzysztof Mierzwicki, Sławomir Szafert, Nurbey Gulia, Jolanta Ejfler. Homoleptic aminophenolates of Zn, Mg and Ca. Synthesis, structure, DFT studies and polymerization activity in ROP of lactides. Dalton Trans. 2014, 43 (6) , 2424-2436. https://doi.org/10.1039/C3DT52868E
    85. Tianjun Yu, Yi Zeng, Jinping Chen, Xiaohui Zhang, Guoqiang Yang, Yi Li. Efficient photochemical production of hydrogen in aqueous solution by simply incorporating a water-insoluble hydrogenase mimic into a hydrogel. J. Mater. Chem. A 2014, 2 (48) , 20500-20505. https://doi.org/10.1039/C4TA04914D
    86. Wei Yi, Haiyan Ma. Magnesium complexes containing biphenyl-based tridentate imino-phenolate ligands for ring-opening polymerization of rac-lactide and α-methyltrimethylene carbonate. Dalton Transactions 2014, 43 (13) , 5200. https://doi.org/10.1039/c3dt53513d
    87. Junpeng Liu, Haiyan Ma. Aluminum complexes with bidentate amido ligands: synthesis, structure and performance on ligand-initiated ring-opening polymerization of rac-lactide. Dalton Transactions 2014, 43 (24) , 9098. https://doi.org/10.1039/c4dt00353e
    88. Andreas Kapelski, Jun Okuda. Ring-opening polymerization of rac - and meso -lactide initiated by indium bis(phenolate) isopropoxy complexes. Journal of Polymer Science Part A: Polymer Chemistry 2013, 51 (23) , 4983-4991. https://doi.org/10.1002/pola.26925
    89. Chullikkattil P. Pradeep, Samar K. Das. Coordination and supramolecular aspects of the metal complexes of chiral N-salicyl-β-amino alcohol Schiff base ligands: Towards understanding the roles of weak interactions in their catalytic reactions. Coordination Chemistry Reviews 2013, 257 (11-12) , 1699-1715. https://doi.org/10.1016/j.ccr.2013.01.028
    90. Yuan Wang, Haiyan Ma. Aluminum complexes of bidentate phenoxy-amine ligands: Synthesis, characterization and catalysis in ring-opening polymerization of cyclic esters. Journal of Organometallic Chemistry 2013, 731 , 23-28. https://doi.org/10.1016/j.jorganchem.2013.02.012
    91. Edward D. Cross, Laura E. N. Allan, Andreas Decken, Michael P. Shaver. Aluminum salen and salan complexes in the ring-opening polymerization of cyclic esters: Controlled immortal and copolymerization of rac -β-butyrolactone and rac -lactide. Journal of Polymer Science Part A: Polymer Chemistry 2013, 51 (5) , 1137-1146. https://doi.org/10.1002/pola.26476
    92. Sungwoo Yoon, So Han Kim, Jungseok Heo, Youngjo Kim. Dimeric aluminum methyl complex bridged by 2-oxy-2-methyl-1-(phenylamino)propane: Synthesis, structure, and use in ring opening polymerization of lactide. Inorganic Chemistry Communications 2013, 29 , 157-159. https://doi.org/10.1016/j.inoche.2012.12.025
    93. Tzu-Lun Huang, Chi-Tien Chen. Aluminium complexes containing pyrazolyl–phenolate ligands as catalysts for ring opening polymerization of ε-caprolactone. Journal of Organometallic Chemistry 2013, 725 , 15-21. https://doi.org/10.1016/j.jorganchem.2012.12.003
    94. Zhongran Dai, Jinjin Zhang, Yuan Gao, Ning Tang, Yong Huang, Jincai Wu. Synthesis and structures of tridentate β-diketiminato zinc phenoxides as catalysts for immortal ring-opening polymerization of l-lactide. Catalysis Science & Technology 2013, 3 (12) , 3268. https://doi.org/10.1039/c3cy00482a
    95. Nduka Ikpo, Jenna C. Flogeras, Francesca M. Kerton. Aluminium coordination complexes in copolymerization reactions of carbon dioxide and epoxides. Dalton Transactions 2013, 42 (25) , 8998. https://doi.org/10.1039/c3dt00049d
    96. Di Li, Ying Peng, Chao Geng, Kaipeng Liu, Dexu Kong. Well-controlled ring-opening polymerization of cyclic esters initiated by dialkylaluminum β-diketiminates. Dalton Transactions 2013, 42 (31) , 11295. https://doi.org/10.1039/c3dt50372k
    97. Jinshui Qiu, Min Lu, Yingming Yao, Yong Zhang, Yaorong Wang, Qi Shen. Synthesis and characterization of bimetallic lanthanide–alkali metal complexes stabilized by aminophenoxy ligands and their catalytic activity for the polymerization of 2,2-dimethyltrimethylene carbonate. Dalton Transactions 2013, 42 (28) , 10179. https://doi.org/10.1039/c3dt50918d
    98. Stuart L. Hancock, Mary F. Mahon, Matthew D. Jones. Salen complexes based on 1,4-diaminocyclohexane and their exploitation for the polymerisation of rac-lactide. New Journal of Chemistry 2013, 37 (7) , 1996. https://doi.org/10.1039/c3nj00111c
    99. Dexu Kong, Ying Peng, Di Li, Yang Li, Pingping Chen, Jingping Qu. Dimethylaluminum complexes bearing a chiral diketiminate ligand: Synthesis, characterization and ring-opening polymerization of ε-caprolactone. Inorganic Chemistry Communications 2012, 22 , 158-161. https://doi.org/10.1016/j.inoche.2012.05.050
    100. Hui-Ju Chuang, Yu-Chu Su, Bao-Tsan Ko, Chu-Chieh Lin. Synthesis and structural characterization of aluminum complexes supported by NNO-tridentate ketiminate ligands: Efficient catalysts for ring-opening polymerization of l-lactide. Inorganic Chemistry Communications 2012, 18 , 38-42. https://doi.org/10.1016/j.inoche.2012.01.004
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