Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide
- Corresponding author: Shao-Feng Liu, shaofengliu@qust.edu.cn Zhi-Bo Li, zbli@qust.edu.cn
Citation: Tong Shi, Quan-De Zheng, Wei-Wei Zuo, Shao-Feng Liu, Zhi-Bo Li. Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 149-156. doi: 10.1007/s10118-018-2039-5
Buchwalter P., Rosé J., Braunstein P.. Multimetallic catalysis based on heterometallic complexes and clusters[J]. Chem. Rev., 2015,115(1):28-126. doi: 10.1021/cr500208k
Hetterscheid D. G. H., Chikkali S. H., de Bruin B., Reek J. N. H.. Binuclear cooperative catalysts for the hydrogenation and hydroformylation of olefins[J]. ChemCatChem, 2013,5(10):2785-2793. doi: 10.1002/cctc.v5.10
Sone T., Yamaguchi A., Matsunaga S., Shibasaki M.. Catalytic asymmetric synthesis of 2, 2-disubstituted terminal epoxides via dimethyloxosulfonium methylide addition to ketones[J]. J. Am. Chem. Soc., 2008,130(31):10078-10079. doi: 10.1021/ja803864p
Matsunaga S., Shibasaki M.. Recent advances in cooperative bimetallic asymmetric catalysis:dinuclear Schiff base complexes[J]. Chem. Commun., 2014,50(9):1044-1057. doi: 10.1039/C3CC47587E
Huang H. H., Zhang C. H., Qin Y. W., Niu H., Dong J. Y.. Synthesis of styryl-capped polypropylene via metallocenemediated coordination polymerization:apply to polypropylene macromolecular engineering[J]. Chinese J. Polym. Sci., 2013,31(4):550-562. doi: 10.1007/s10118-013-1261-4
Wang J., Li H. M., Guo J. P., Huang Q. G., Yi J. J., Liu Y. F., Gao K. J., Yang W. T.. Coral-shaped and core-shell structure copolyethylene nanocomposites particles prepared by in situ coordination polymerization[J]. Chinese J. Polym. Sci., 2015,33(12):1650-1660. doi: 10.1007/s10118-015-1719-7
Delferro M., Marks T. J.. Multinuclear olefin polymerization catalysts[J]. Chem. Rev., 2011,111(3):2450-2485. doi: 10.1021/cr1003634
Zhang J., Liu S., Zuo W., Ye H., Li Z.. Synthesis of dinuclear aluminum complexes bearing bis-phenolate ligand and application in ring-opening polymerization of ε-caprolactone[J]. New J. Chem., 2017,41(6):2358-2363. doi: 10.1039/C6NJ03818B
Xiang S., Shao J., Li G., Bian X. C., Feng L. D., Chen X. S., Liu F. Q., Huang S. Y.. Effects of molecular weight on the crystallization and melting behaviors of poly(L-lactide)[J]. Chinese J. Polym. Sci., 2016,34(1):69-76. doi: 10.1007/s10118-016-1727-2
Huang H. C., Wang B., Zhang Y. P., Li Y. S.. Bimetallic aluminum complexes with cyclic β-ketiminato ligands:the cooperative effect improves their capability in polymerization of lactide and ε-caprolactone[J]. Polym. Chem., 2016,7(37):5819-5827. doi: 10.1039/C6PY01092J
Wu L. Y., Fan D. D., Lu X. Q., Lu R.. Ring-opening copolymerization of cyclohexene oxide and maleic anhydride catalyzed by mononuclear[Zn(L)(H2O)] or binuclear[Zn2(L)(OAc)2 (H2O)] complex based on the Salen-type Schiff-base ligand[J]. Chinese J. Polym. Sci., 2014,32(6):768-777. doi: 10.1007/s10118-014-1425-x
Sun S., Nie K., Tan Y., Zhao B., Zhang Y., Shen Q., Yao Y.. Bimetallic lanthanide amido complexes as highly active initiators for the ring-opening polymerization of lactides[J]. Dalton Trans., 2013,42(8):2870-2878. doi: 10.1039/C2DT31597A
Wang Y., Ma H.. Exploitation of dinuclear salan aluminum complexes for versatile copolymerization of ε-caprolactone and L-lactide[J]. Chem. Commun., 2012,48(53):6729-6731. doi: 10.1039/c2cc31716h
Saha T. K., Ramkumar V., Chakraborty D.. Salen complexes of zirconium and hafnium:synthesis, structural characterization, controlled hydrolysis, and solvent-free ring-opening polymerization of cyclic esters and lactides[J]. Inorg. Chem., 2011,50(7):2720-2722. doi: 10.1021/ic1025262
Li W., Wu W., Wang Y., Yao Y., Zhang Y., Shen Q.. Bimetallic aluminum alkyl complexes as highly active initiators for the polymerization of ε-caprolactone[J]. Dalton Trans., 2011,40(43):11378-11381. doi: 10.1039/c1dt11380a
Yao W., Mu Y., Gao A., Gao W., Ye L.. Bimetallic anilido-aldimine Al or Zn complexes for efficient ring-opening polymerization of ε-caprolactone[J]. Dalton Trans., 2008:3199-3206.
Arbaoui A., Redshaw C., Hughes D. L.. Multinuclear alkylaluminum macrocyclic Schiff base complexes:influence of procatalyst structure on the ring opening polymerisation of ε-caprolactone[J]. Chem. Commun., 2008:4717-4719.
Williams C. K., Brooks N. R., Hillmyer M. A., Tolman W. B.. Metalloenzyme inspired dizinc catalyst for the polymerization of lactide[J]. Chem. Commun., 2002:2132-2133.
Kan C., Ma H.. Copolymerization of L-lactide and ε-caprolactone catalyzed by mono-and dinuclear salen aluminum complexes bearing bulky 6, 6'-dimethylbiphenyl-bridge:random and tapered copolymer[J]. RSC Adv., 2016,6(53):47402-47409. doi: 10.1039/C6RA07374C
Chen L., Li W., Yuan D., Zhang Y., Shen Q., Yao Y.. Syntheses of mononuclear and dinuclear aluminum complexes stabilized by Phenolato ligands and their applications in the polymerization of ε-caprolactone:a comparative study[J]. Inorg. Chem., 2015,54(10):4699-4708. doi: 10.1021/acs.inorgchem.5b00022
Wei Y., Wang S., Zhou S.. Aluminum alkyl complexes:synthesis, structure, and application in ROP of cyclic esters[J]. Dalton Trans., 2016,45(11):4471-4485. doi: 10.1039/C5DT04240B
Li W., Ouyang H., Chen L., Yuan D., Zhang Y., Yao Y.. A comparative study on dinuclear and mononuclear aluminum methyl complexes bearing piperidyl-phenolato ligands in ROP of epoxides[J]. Inorg. Chem., 2016,55(13):6520-6524. doi: 10.1021/acs.inorgchem.6b00639
Li L., Liu B., Liu D., Wu C., Li S., Liu B., Cui D.. Copolymerization of ε-caprolactone and L-lactide catalyzed by multinuclear aluminum complexes:an immortal approach[J]. Organometallics, 2014,33(22):6474-6480. doi: 10.1021/om5008264
Liu S., Motta A., Mouat A. R., Delferro M., Marks T. J.. Very large cooperative effects in heterobimetallic titanium-chromium catalysts for ethylene polymerization/copolymerization[J]. J. Am. Chem. Soc., 2014,136(29):10460-10469. doi: 10.1021/ja5046742
Liu S., Motta A., Delferro M., Marks , T. J.. Synthesis, characterization, and heterobimetallic cooperation in a titanium-chromium catalyst for highly branched polyethylenes.[J]. J. Am. Chem. Soc., 2013,135(24):8830-8833. doi: 10.1021/ja4039505
Inoue S.. Immortal polymerization:the outset, development, and application[J]. J. Polym. Sci., Part A:Polym. Chem., 2000,38(16):2861-2871. doi: 10.1002/(ISSN)1099-0518
Cheung K. C., Wong W. L., So M. H., Zhou Z. Y., Yan S. C., Wong K. Y.. A dinuclear ruthenium catalyst with a confined cavity:selectivity in the addition of aliphatic carboxylic acids to phenylacetylene[J]. Chem. Commun., 2013,49(7):710-712. doi: 10.1039/C2CC38454J
Kendall J. K., Shechter H.. Intramolecular behaviors of anthryldicarbenic systems:dibenzo[b, f]pentalene and 1H, 5Hdicyclobuta[de, kl]anthracene[J]. J. Org. Chem., 2001,66(20):6643-6649. doi: 10.1021/jo010404p
Dolomanov O. V., Bourhis L. J., Gildea R. J., Howard J. A. K., Puschmann H.. OLEX2:a complete structure solution, refinement and analysis program[J]. J. Appl. Cryst., 2009,42:339-341. doi: 10.1107/S0021889808042726
Sheldrick G. M.. A short story of SHELX[J]. Acta Cryst. A, 2008,64:112-122. doi: 10.1107/S0108767307043930
Sheldrick, G. M., "Shelxtl PC: an integrated system for solving, refining, and displaying crystal structures from diffraction data", Version 6. 014, Bruker AXS, Madison, WI, 2000.
Ulatowski F., Jurczak J.. Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms[J]. J. Org. Chem., 2015,80(9):4235-4243. doi: 10.1021/acs.joc.5b00403
Kim Y. K., Lee H. N., Singh N. J., Choi H. J., Xue J. Y., Kim K. S., Yoon J., Hyun M. H.. Anthracene derivatives bearing thiourea and glucopyranosyl groups for the highly selective chiral recognition of amino acids:opposite chiral selectivities from similar binding units[J]. J. Org. Chem., 2008,73(1):301-304. doi: 10.1021/jo7022813
Salata M. R., Marks T. J.. Catalyst nuclearity effects in olefin polymerization[J]. enhanced activity and comonomer enchainment in ethylene + olefin copolymerizations mediated by bimetallic group 4 phenoxyiminato catalysts. Macromolecules, 2009,42(6):1920-1933.
Han H. L., Liu Y., Liu J. Y., Nomura K., Li Y. S.. Synthesis of binuclear phenoxyimino organoaluminum complexes and their use as the catalyst precursors for efficient ring-opening polymerisation of ε-caprolactone[J]. Dalton Trans., 2013,42(34):12346-12353. doi: 10.1039/c3dt50264c
Zhang W., Wang Y., Sun W. H., Wang L., Redshaw C.. Dimethylaluminium aldiminophenolates:synthesis, characterization and ring-opening polymerization behavior towards lactides[J]. Dalton Trans., 2012,41(38):11587-11596. doi: 10.1039/c2dt31215h
Zhao W., Wang Y., Liu X., Chen X., Cui D., Chen E. Y. X.. Protic compound mediated living cross-chain-transfer polymerization of rac-lactide:synthesis of isotactic (crystalline)-heterotactic (amorphous) stereomultiblock polylactide[J]. Chem. Commun., 2012,48(51):6375-6377. doi: 10.1039/c2cc32680a
Zhao W., Cui D., Liu X., Chen X.. Facile synthesis of hydroxyl-ended, highly stereoregular, star-shaped poly(lactide) from immortal ROP of rac-lactide and kinetics study[J]. Macromolecules, 2010,43(16):6678-6684. doi: 10.1021/ma101202g
Helou M., Miserque O., Brusson J. M., Carpentier J. F., Guillaume S. M.. Ultraproductive, zinc-mediated, immortal ring-opening polymerization of trimethylene carbonate[J]. Chem. Eur. J., 2008,14(29):8772-8775. doi: 10.1002/chem.200801416
Liu J., Iwasa N., Nomura K.. Synthesis of Al complexes containing phenoxy-imine ligands and their use as the catalyst precursors for efficient living ring-opening polymerisation of ε-caprolactone[J]. Dalton Trans., 2008:3978-3988.
Liu S., Zhang J., Zuo W., Zhang W., Sun W. H., Ye H., Li Z.. Synthesis of aluminum complexes bearing 8-anilide-5, 6, 7-trihydroquinoline ligands:highly active catalyst precursors for ring-opening polymerization of cyclic esters[J]. Polymers, 2017,9(3). doi: 10.3390/polym9030083
Luo W., Shi T., Liu S., Zuo W., Li Z.. Well-designed unsymmetrical Salphen-Al complexes:synthesis, characterization, and ring-opening polymerization catalysis[J]. Organometallics, 2017,36(9):1736-1742. doi: 10.1021/acs.organomet.7b00106
Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Jun LI , Huipeng LI , Hua ZHAO , Qinlong LIU . Preparation and photocatalytic performance of AgNi bimetallic modified polyhedral bismuth vanadate. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 601-612. doi: 10.11862/CJIC.20230401
Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
Zimo Peng , Quan Zhang , Gaocan Qi , Hao Zhang , Qian Liu , Guangzhi Hu , Jun Luo , Xijun Liu . Nanostructured Pt@RuOx catalyst for boosting overall acidic seawater splitting. Chinese Journal of Structural Chemistry, 2024, 43(1): 100191-100191. doi: 10.1016/j.cjsc.2023.100191
Wen LUO , Lin JIN , Palanisamy Kannan , Jinle HOU , Peng HUO , Jinzhong YAO , Peng WANG . Preparation of high-performance supercapacitor based on bimetallic high nuclearity titanium-oxo-cluster based electrodes. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 782-790. doi: 10.11862/CJIC.20230418
Yufei Jia , Fei Li , Ke Fan . Surface reconstruction of Cu-based bimetallic catalysts for electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100255-100255. doi: 10.1016/j.cjsc.2024.100255
Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
Ji Chen , Yifan Zhao , Shuwen Zhao , Hua Zhang , Youyu Long , Lingfeng Yang , Min Xi , Zitao Ni , Yao Zhou , Anran Chen . Heterogeneous bimetallic oxides/phosphides nanorod with upshifted d band center for efficient overall water splitting. Chinese Chemical Letters, 2024, 35(9): 109268-. doi: 10.1016/j.cclet.2023.109268
Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
Lumin Zheng , Ying Bai , Chuan Wu . Multi-electron reaction and fast Al ion diffusion of δ-MnO2 cathode materials in rechargeable aluminum batteries via first-principle calculations. Chinese Chemical Letters, 2024, 35(4): 108589-. doi: 10.1016/j.cclet.2023.108589