Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide

Tong Shi; Quan-De Zheng; Wei-Wei Zuo; Shao-Feng Liu; Zhi-Bo Li

doi:10.1007/s10118-018-2039-5

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Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide

Articles | Updated：2021-02-18

- Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide
- Bimetallic Aluminum Complexes Supported by Bis(salicylaldimine) Ligand: Synthesis, Characterization and Ring-opening Polymerization of Lactide
- Chinese Journal of Polymer Science 2018年36卷第2期页码：149-156
- Affiliations：
  
  a.Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department; School of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  b.State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Donghua University, Shanghai 201620, China
- Author bio：
  
  E-mail shaofengliu@qust.edu.cn (S.F.L.)
  E-mail zbli@qust.edu.cn (Z.B.L.)
- Funds：
  
  Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://dx.doi.org/10.1007/s10118-018-2039-5.
- DOI：10.1007/s10118-018-2039-5
  中图分类号：
- 收稿：2017-08-10，
  
  录用：2017-9-8，
  
  网络首发：2017-11-01，
  
  纸质出版：2018-02-05
- Accepted：
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Tong Shi, Quan-De Zheng, Wei-Wei Zuo, 等. 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.

Tong Shi, Quan-De Zheng, Wei-Wei Zuo, et al. 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.
Tong Shi, Quan-De Zheng, Wei-Wei Zuo, 等. 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.

Tong Shi, Quan-De Zheng, Wei-Wei Zuo, et al. 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.

摘要

Abstract

Two types of bifunctional bis(salicylaldimine) ligands (

syn

-L

and

anti

-L

) were designed and synthesized to support bimetallic aluminum complexes. Owing to the rigid anthracene skeleton

syn

-L

and

anti

-L

successfully locked two Al centers in close proximity (

syn

-Al

) and far apart (

anti

-Al

)

respectively. The distance between two Al centers in

syn

-Al

was defined by X-ray diffraction as 6.665 Å

which is far shorter than that in

anti

-Al

. In the presence of stoichiometrical BnOH

syn

-Al

and

anti

-Al

were both efficient for ring-opening polymerization (ROP) of

rac

-LA with the former being more active. In the presence of excess BnOH

syn

-Al

showed an efficient and immortal feature

consistent with high conversions

matched

narrow molecular weight distributions and end group fidelity

while

anti

-Al

had a much lower activity or even became entirely inactive due to rapid decomposition

indicated by

in situ

H-NMR experiments of Al complexes with BnOH.

关键词

Keywords

references

P. Buchwalter , J. Rosé , P. Braunstein . Multimetallic catalysis based on heterometallic complexes and clusters . Chem. Rev. , 2015 . 115 ( 1 ): 28 - 126 . DOI: 10.1021/cr500208k http://doi.org/10.1021/cr500208k .

D. G. H. Hetterscheid , S. H. Chikkali , B. de Bruin , J. N. H. Reek . Binuclear cooperative catalysts for the hydrogenation and hydroformylation of olefins . ChemCatChem , 2013 . 5 ( 10 ): 2785 - 2793 . DOI: 10.1002/cctc.v5.10 http://doi.org/10.1002/cctc.v5.10 .

T. Sone , A. Yamaguchi , S. Matsunaga , M. Shibasaki . Catalytic asymmetric synthesis of 2, 2-disubstituted terminal epoxides via dimethyloxosulfonium methylide addition to ketones . J. Am. Chem. Soc. , 2008 . 130 ( 31 ): 10078 - 10079 . DOI: 10.1021/ja803864p http://doi.org/10.1021/ja803864p .

S. Matsunaga , M. Shibasaki . Recent advances in cooperative bimetallic asymmetric catalysis:dinuclear Schiff base complexes . Chem. Commun. , 2014 . 50 ( 9 ): 1044 - 1057 . DOI: 10.1039/C3CC47587E http://doi.org/10.1039/C3CC47587E .

H. H. Huang , C. H. Zhang , Y. W. Qin , H. Niu , J. Y. Dong . Synthesis of styryl-capped polypropylene via metallocenemediated coordination polymerization:apply to polypropylene macromolecular engineering . Chinese J. Polym. Sci. , 2013 . 31 ( 4 ): 550 - 562 . DOI: 10.1007/s10118-013-1261-4 http://doi.org/10.1007/s10118-013-1261-4 .

J. Wang , H. M. Li , J. P. Guo , Q. G. Huang , J. J. Yi , Y. F. Liu , K. J. Gao , W. T. Yang . Coral-shaped and core-shell structure copolyethylene nanocomposites particles prepared by in situ coordination polymerization . Chinese J. Polym. Sci. , 2015 . 33 ( 12 ): 1650 - 1660 . DOI: 10.1007/s10118-015-1719-7 http://doi.org/10.1007/s10118-015-1719-7 .

M. Delferro , T. J. Marks . Multinuclear olefin polymerization catalysts . Chem. Rev. , 2011 . 111 ( 3 ): 2450 - 2485 . DOI: 10.1021/cr1003634 http://doi.org/10.1021/cr1003634 .

J. Zhang , S. Liu , W. Zuo , H. Ye , Z. Li . Synthesis of dinuclear aluminum complexes bearing bis-phenolate ligand and application in ring-opening polymerization of ε -caprolactone . New J. Chem. , 2017 . 41 ( 6 ): 2358 - 2363 . DOI: 10.1039/C6NJ03818B http://doi.org/10.1039/C6NJ03818B .

S. Xiang , J. Shao , G. Li , X. C. Bian , L. D. Feng , X. S. Chen , F. Q. Liu , S. Y. Huang . Effects of molecular weight on the crystallization and melting behaviors of poly(L-lactide) . Chinese J. Polym. Sci. , 2016 . 34 ( 1 ): 69 - 76 . DOI: 10.1007/s10118-016-1727-2 http://doi.org/10.1007/s10118-016-1727-2 .

H. C. Huang , B. Wang , Y. P. Zhang , Y. S. Li . Bimetallic aluminum complexes with cyclic β -ketiminato ligands:the cooperative effect improves their capability in polymerization of lactide and ε -caprolactone . Polym. Chem. , 2016 . 7 ( 37 ): 5819 - 5827 . DOI: 10.1039/C6PY01092J http://doi.org/10.1039/C6PY01092J .

L. Y. Wu , D. D. Fan , X. Q. Lu , R. Lu . Ring-opening copolymerization of cyclohexene oxide and maleic anhydride catalyzed by mononuclear[Zn(L)(H 2 O)] or binuclear[Zn 2 (L)(OAc) 2 (H 2 O)] complex based on the Salen-type Schiff-base ligand . Chinese J. Polym. Sci. , 2014 . 32 ( 6 ): 768 - 777 . DOI: 10.1007/s10118-014-1425-x http://doi.org/10.1007/s10118-014-1425-x .

S. Sun , K. Nie , Y. Tan , B. Zhao , Y. Zhang , Q. Shen , Y. Yao . Bimetallic lanthanide amido complexes as highly active initiators for the ring-opening polymerization of lactides . Dalton Trans. , 2013 . 42 ( 8 ): 2870 - 2878 . DOI: 10.1039/C2DT31597A http://doi.org/10.1039/C2DT31597A .

Y. Wang , H. Ma . Exploitation of dinuclear salan aluminum complexes for versatile copolymerization of ε -caprolactone and L-lactide . Chem. Commun. , 2012 . 48 ( 53 ): 6729 - 6731 . DOI: 10.1039/c2cc31716h http://doi.org/10.1039/c2cc31716h .

T. K. Saha , V. Ramkumar , D. Chakraborty . Salen complexes of zirconium and hafnium:synthesis, structural characterization, controlled hydrolysis, and solvent-free ring-opening polymerization of cyclic esters and lactides . Inorg. Chem. , 2011 . 50 ( 7 ): 2720 - 2722 . DOI: 10.1021/ic1025262 http://doi.org/10.1021/ic1025262 .

W. Li , W. Wu , Y. Wang , Y. Yao , Y. Zhang , Q. Shen . Bimetallic aluminum alkyl complexes as highly active initiators for the polymerization of ε-caprolactone . Dalton Trans. , 2011 . 40 ( 43 ): 11378 - 11381 . DOI: 10.1039/c1dt11380a http://doi.org/10.1039/c1dt11380a .

W. Yao , Y. Mu , A. Gao , W. Gao , L. Ye . Bimetallic anilido-aldimine Al or Zn complexes for efficient ring-opening polymerization of ε-caprolactone . Dalton Trans. , 2008 . 3199 - 3206 . .

A. Arbaoui , C. Redshaw , D. L. Hughes . Multinuclear alkylaluminum macrocyclic Schiff base complexes:influence of procatalyst structure on the ring opening polymerisation of ε-caprolactone . Chem. Commun. , 2008 . 4717 - 4719 . https://www.researchgate.net/publication/23295115_Multinuclear_alkylaluminium_macrocyclic_Schiff_base_complexes_Influence_of_procatalyst_structure_on_the_ring_opening_polymerisation_of_e-caprolactone https://www.researchgate.net/publication/23295115_Multinuclear_alkylaluminium_macrocyclic_Schiff_base_complexes_Influence_of_procatalyst_structure_on_the_ring_opening_polymerisation_of_e-caprolactone , .

C. K. Williams , N. R. Brooks , M. A. Hillmyer , W. B. Tolman . Metalloenzyme inspired dizinc catalyst for the polymerization of lactide . Chem. Commun. , 2002 . 2132 - 2133 . https://www.researchgate.net/publication/11099369_Metalloenzyme_inspired_dizinc_catalyst_for_the_polymerization_of_lactide https://www.researchgate.net/publication/11099369_Metalloenzyme_inspired_dizinc_catalyst_for_the_polymerization_of_lactide , .

C. Kan , H. Ma . 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 . RSC Adv. , 2016 . 6 ( 53 ): 47402 - 47409 . DOI: 10.1039/C6RA07374C http://doi.org/10.1039/C6RA07374C .

L. Chen , W. Li , D. Yuan , Y. Zhang , Q. Shen , Y. Yao . Syntheses of mononuclear and dinuclear aluminum complexes stabilized by Phenolato ligands and their applications in the polymerization of ε -caprolactone:a comparative study . Inorg. Chem. , 2015 . 54 ( 10 ): 4699 - 4708 . DOI: 10.1021/acs.inorgchem.5b00022 http://doi.org/10.1021/acs.inorgchem.5b00022 .

Y. Wei , S. Wang , S. Zhou . Aluminum alkyl complexes:synthesis, structure, and application in ROP of cyclic esters . Dalton Trans. , 2016 . 45 ( 11 ): 4471 - 4485 . DOI: 10.1039/C5DT04240B http://doi.org/10.1039/C5DT04240B .

W. Li , H. Ouyang , L. Chen , D. Yuan , Y. Zhang , Y. Yao . A comparative study on dinuclear and mononuclear aluminum methyl complexes bearing piperidyl-phenolato ligands in ROP of epoxides . Inorg. Chem. , 2016 . 55 ( 13 ): 6520 - 6524 . DOI: 10.1021/acs.inorgchem.6b00639 http://doi.org/10.1021/acs.inorgchem.6b00639 .

L. Li , B. Liu , D. Liu , C. Wu , S. Li , B. Liu , D. Cui . Copolymerization of ε -caprolactone and L-lactide catalyzed by multinuclear aluminum complexes:an immortal approach . Organometallics , 2014 . 33 ( 22 ): 6474 - 6480 . DOI: 10.1021/om5008264 http://doi.org/10.1021/om5008264 .

S. Liu , A. Motta , A. R. Mouat , M. Delferro , T. J. Marks . Very large cooperative effects in heterobimetallic titanium-chromium catalysts for ethylene polymerization/copolymerization . J. Am. Chem. Soc. , 2014 . 136 ( 29 ): 10460 - 10469 . DOI: 10.1021/ja5046742 http://doi.org/10.1021/ja5046742 .

S. Liu , A. Motta , M. Delferro , Marks , J. T. . Synthesis, characterization, and heterobimetallic cooperation in a titanium-chromium catalyst for highly branched polyethylenes. . J. Am. Chem. Soc. , 2013 . 135 ( 24 ): 8830 - 8833 . DOI: 10.1021/ja4039505 http://doi.org/10.1021/ja4039505 .

S. Inoue . Immortal polymerization:the outset, development, and application . J. Polym. Sci., Part A:Polym. Chem. , 2000 . 38 ( 16 ): 2861 - 2871 . DOI: 10.1002/(ISSN)1099-0518 http://doi.org/10.1002/(ISSN)1099-0518 .

K. C. Cheung , W. L. Wong , M. H. So , Z. Y. Zhou , S. C. Yan , K. Y. Wong . A dinuclear ruthenium catalyst with a confined cavity:selectivity in the addition of aliphatic carboxylic acids to phenylacetylene . Chem. Commun. , 2013 . 49 ( 7 ): 710 - 712 . DOI: 10.1039/C2CC38454J http://doi.org/10.1039/C2CC38454J .

J. K. Kendall , H. Shechter . Intramolecular behaviors of anthryldicarbenic systems:dibenzo[b, f]pentalene and 1H, 5Hdicyclobuta[de, kl]anthracene . J. Org. Chem. , 2001 . 66 ( 20 ): 6643 - 6649 . DOI: 10.1021/jo010404p http://doi.org/10.1021/jo010404p .

O. V. Dolomanov , L. J. Bourhis , R. J. Gildea , J. A. K. Howard , H. Puschmann . OLEX2:a complete structure solution, refinement and analysis program . J. Appl. Cryst. , 2009 . 42 339 - 341 . DOI: 10.1107/S0021889808042726 http://doi.org/10.1107/S0021889808042726 .

G. M. Sheldrick . A short story of SHELX . Acta Cryst. A , 2008 . 64 112 - 122 . DOI: 10.1107/S0108767307043930 http://doi.org/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.

F. Ulatowski , J. Jurczak . Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms . J. Org. Chem. , 2015 . 80 ( 9 ): 4235 - 4243 . DOI: 10.1021/acs.joc.5b00403 http://doi.org/10.1021/acs.joc.5b00403 .

Y. K. Kim , H. N. Lee , N. J. Singh , H. J. Choi , J. Y. Xue , K. S. Kim , J. Yoon , M. H. Hyun . Anthracene derivatives bearing thiourea and glucopyranosyl groups for the highly selective chiral recognition of amino acids:opposite chiral selectivities from similar binding units . J. Org. Chem. , 2008 . 73 ( 1 ): 301 - 304 . DOI: 10.1021/jo7022813 http://doi.org/10.1021/jo7022813 .

M. R. Salata , T. J. Marks . Catalyst nuclearity effects in olefin polymerization . enhanced activity and comonomer enchainment in ethylene + olefin copolymerizations mediated by bimetallic group 4 phenoxyiminato catalysts. Macromolecules , 2009 . 42 ( 6 ): 1920 - 1933 . .

H. L. Han , Y. Liu , J. Y. Liu , K. Nomura , Y. S. Li . Synthesis of binuclear phenoxyimino organoaluminum complexes and their use as the catalyst precursors for efficient ring-opening polymerisation of ε-caprolactone . Dalton Trans. , 2013 . 42 ( 34 ): 12346 - 12353 . DOI: 10.1039/c3dt50264c http://doi.org/10.1039/c3dt50264c .

W. Zhang , Y. Wang , W. H. Sun , L. Wang , C. Redshaw . Dimethylaluminium aldiminophenolates:synthesis, characterization and ring-opening polymerization behavior towards lactides . Dalton Trans. , 2012 . 41 ( 38 ): 11587 - 11596 . DOI: 10.1039/c2dt31215h http://doi.org/10.1039/c2dt31215h .

W. Zhao , Y. Wang , X. Liu , X. Chen , D. Cui , E. Y. X. Chen . Protic compound mediated living cross-chain-transfer polymerization of rac -lactide:synthesis of isotactic (crystalline)-heterotactic (amorphous) stereomultiblock polylactide . Chem. Commun. , 2012 . 48 ( 51 ): 6375 - 6377 . DOI: 10.1039/c2cc32680a http://doi.org/10.1039/c2cc32680a .

W. Zhao , D. Cui , X. Liu , X. Chen . Facile synthesis of hydroxyl-ended, highly stereoregular, star-shaped poly(lactide) from immortal ROP of rac -lactide and kinetics study . Macromolecules , 2010 . 43 ( 16 ): 6678 - 6684 . DOI: 10.1021/ma101202g http://doi.org/10.1021/ma101202g .

M. Helou , O. Miserque , J. M. Brusson , J. F. Carpentier , S. M. Guillaume . Ultraproductive, zinc-mediated, immortal ring-opening polymerization of trimethylene carbonate . Chem. Eur. J. , 2008 . 14 ( 29 ): 8772 - 8775 . DOI: 10.1002/chem.200801416 http://doi.org/10.1002/chem.200801416 .

J. Liu , N. Iwasa , K. Nomura . Synthesis of Al complexes containing phenoxy-imine ligands and their use as the catalyst precursors for efficient living ring-opening polymerisation of ε-caprolactone . Dalton Trans. , 2008 . 3978 - 3988 . .

S. Liu , J. Zhang , W. Zuo , W. Zhang , W. H. Sun , H. Ye , Z. Li . Synthesis of aluminum complexes bearing 8-anilide-5, 6, 7-trihydroquinoline ligands:highly active catalyst precursors for ring-opening polymerization of cyclic esters . Polymers , 2017 . 9 ( 3 ): DOI: 10.3390/polym9030083 http://doi.org/10.3390/polym9030083 .

W. Luo , T. Shi , S. Liu , W. Zuo , Z. Li . Well-designed unsymmetrical Salphen-Al complexes:synthesis, characterization, and ring-opening polymerization catalysis . Organometallics , 2017 . 36 ( 9 ): 1736 - 1742 . DOI: 10.1021/acs.organomet.7b00106 http://doi.org/10.1021/acs.organomet.7b00106 .

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