Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO<sub>2</sub> and Propylene Oxide

Chun-Wei Zhuo; Yu-Sheng Qin; Xian-Hong Wang; Fo-Song Wang

doi:10.1007/s10118-018-2093-z

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Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO₂ and Propylene Oxide

Articles | Updated：2021-02-18

- Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO₂ and Propylene Oxide
- Chinese Journal of Polymer Science Vol. 36, Issue 2, Pages: 252-260(2018)
- Affiliations：
  
  a.Key Laboratory of Polymer Ecomaterial, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  b.University of Science and Technology of China, Hefei 230026, China
- Author bio：
  
  Yu-Sheng Qin, E-mail ysqin@ciac.ac.cn
  Xian-Hong Wang, E-mail xhwang@ciac.ac.cn
- Funds：
- DOI：10.1007/s10118-018-2093-z
  CLC：
- Received：06 November 2017，
  
  Accepted：15 November 2017，
  
  Online First：29 November 2017，
  
  Published：05 February 2018
- Accepted：
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Chun-Wei Zhuo, Yu-Sheng Qin, Xian-Hong Wang, et al. Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO₂ and Propylene Oxide[J]. Chinese Journal of Polymer Science, 2018, 36(2): 252-260. DOI: 10.1007/s10118-018-2093-z.
DOI：

Chun-Wei Zhuo, Yu-Sheng Qin, Xian-Hong Wang, et al. Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO₂ and Propylene Oxide[J]. Chinese Journal of Polymer Science, 2018, 36(2): 252-260. DOI: 10.1007/s10118-018-2093-z. DOI：

摘要

Abstract

Aluminum porphyrin complexes are heavy-metal-free and soil-tolerant green catalysts for the copolymerization of CO

and propylene oxide (PO)

but they suffer from relatively poor poly(propylene carbonate) (PPC) selectivity. Herein

steric hindrance porphyrin ligand was used to enhance the PPC selectivity. Typically

a bulky anthracene-like group was incorporated into the porphyrin ring to form 5

20-tetra(1

8-octahydro-1

4:5

8-dimethanoanthracen-9-yl) porphyrin

the aluminum porphyrin complex with this ligand

in combination with bis(triphenylphosphine) iminium chloride as a co-catalyst

produced completely alternate PPC. Additionally

the obtained PPC showed high regioselectivity

with a head-to-tail linkage content (HT) of 92%. Therefore

we demonstrated that introduction of bulky steric ligand into the porphyrin ring could reduce the propylene oxide homopolymerization activity leading to excellent PPC selectivity

and improve regioselectivity for the PO ring-opening during the copolymerization.

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references

S Inoue , H Koinuma , T Tsuruta . Copolymerization of carbon dioxide and epoxide with organometallic compounds . Makromol. Chem. , 1969 . 130 210 - 220 . DOI: 10.1002/macp.1969.021300112 http://doi.org/10.1002/macp.1969.021300112 .

S Inoue , H Koinuma , T Tsuruta . Copolymerization of carbon dioxide and epoxide . J. Polym. Sci., Part B:Polym. Lett. , 1969 . 7 287 - 292 . DOI: 10.1002/pol.1969.110070408 http://doi.org/10.1002/pol.1969.110070408 .

B. Y. Liu , X. J. Zhao , X. H. Wang , F. S. Wang . Copolymerization of carbon dioxide and propylene oxidewith Ln(CCl 3 COO) 3 -based catalyst:the role of rare-earth compound in the catalytic system . J. Polym. Sci., Part A:Polym. Chem. , 2001 . 39 2751 - 2754 . http://www.whxb.pku.edu.cn/EN/abstract/abstract22893.shtml http://www.whxb.pku.edu.cn/EN/abstract/abstract22893.shtml , .

Z. L. Quan , X. H. Wang , X. J. Zhao , F. S. Wang . Copolymerization of CO 2 and propylene oxide under rare earth ternarycatalyst:design of ligand in yttrium complex . Polymer , 2003 . 44 5605 - 5610 . DOI: 10.1016/S0032-3861(03)00561-5 http://doi.org/10.1016/S0032-3861(03)00561-5 .

R. L. Paddock , S. T. Nguyen . Chemical CO 2 fixation:Cr(Ⅲ) salen complexes as highly efficient catalysts for the coupling of CO 2 and epoxides . J. Am. Chem. Soc. , 2001 . 123 11498 - 11499 . DOI: 10.1021/ja0164677 http://doi.org/10.1021/ja0164677 .

D. J. Darensbourg , J. C. Yarbrough . Mechanistic aspects of the copolymerization reaction of carbon dioxide and epoxides, using a chiral salen chromium chloride catalyst . J. Am. Chem. Soc. , 2002 . 124 6335 - 6342 . DOI: 10.1021/ja012714v http://doi.org/10.1021/ja012714v .

D. J. Darensbourg , J. C. Yarbrough , C. Ortiz , C. C. Fang . Comparative kinetic studies of the copolymerization of cyclohexene oxide and propylene oxide with carbon dioxide in the presence of chromium salen derivatives. In situ FTIR measurements of copolymer vs cyclic carbonate production . J. Am. Chem. Soc. , 2003 . 125 7586 - 7591 . .

Z.Q. Qin , C. M. Thomas , S. Lee , G. W. Coates . Cobalt-based complexes for the copolymerization of propylene oxide and CO 2 :active and selective catalysts for polycarbonate synthesis . Angew. Chem. Int. Ed. , 2003 . 42 5484 - 5487 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

K. Nakano , T. Kamada , K. Nozaki . Selective formation of polycarbonate over cyclic carbonate:copolymerization of epoxides with carbon dioxide catalyzed by a cobalt(Ⅲ) complex with a piperidiniumend-capping arm . Angew. Chem. Int. Ed. , 2006 . 45 7274 - 7277 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

W. M. Ren , Z. W. Liu , Y. Q. Wen , R. Zhang , X. B. Lu . Mechanistic aspects of the copolymerization of CO 2 withepoxides using a thermally stable single-site cobalt(Ⅲ)catalyst . J. Am. Chem. Soc. , 2009 . 131 11509 - 11518 . DOI: 10.1021/ja9033999 http://doi.org/10.1021/ja9033999 .

E. K. Noh , S. J. Na , S. Sujith , S. W. Kim , B. Y. Lee . Two components in a molecule:highly efficient and thermally robust catalytic system for CO 2 /epoxide copolymerization . J. Am. Chem. Soc. , 2007 . 129 8082 - 8083 . DOI: 10.1021/ja071290n http://doi.org/10.1021/ja071290n .

S. Sujith , J. K. Min , J. E. Seong , S. J. Na , B. Y. Lee . A highly active and recyclable catalytic system for CO 2 /propylene oxide copolymerization . Angew. Chem. Int. Ed. , 2008 . 47 7306 - 7309 . DOI: 10.1002/anie.v47:38 http://doi.org/10.1002/anie.v47:38 .

S. J. Na , S. Sujith , A. Cyriac , B. E. Kim , J. Yoo , Y. K. Kang , S. J. Han , C. Lee , B. Y. Lee . Elucidation of the structure of a highly active catalytic system for CO 2 /epoxide copolymerization:a salen-cobaltate complex of an unusual binding mode . Inorg. Chem. , 2009 . 48 10455 - 10465 . DOI: 10.1021/ic901584u http://doi.org/10.1021/ic901584u .

A. Cyriac , J. Y. Jeon , J. K. Varghese , J. H. Park , S. Y. Choi , Y. K. Chung , B. Y. Lee . Unusual coordination mode of tetradentate Schiff base cobalt(Ⅲ) complexes . Dalton Trans. , 2012 . 41 1444 - 1447 . DOI: 10.1039/C2DT11871H http://doi.org/10.1039/C2DT11871H .

N Takeda , S. Inoue . Polymerization of 1, 2-epoxypropane and copolymerizationwith carbon dioxide catalyzed by metalloporphyrins . Makromol Chem. , 1978 . 179 1377 - 1381 . DOI: 10.1002/macp.1978.021790529 http://doi.org/10.1002/macp.1978.021790529 .

D. J. Darensbourg , D. R. Billodeaux . Aluminum salen complexes and tetrabutylammonium salts:abinary catalytic system for production of polycarbonates from CO 2 and cyclohexene oxide . Inorg. Chem. , 2005 . 44 1433 - 1442 . DOI: 10.1021/ic048508g http://doi.org/10.1021/ic048508g .

M. R. Kember , P. D. Knight , P. T. R. Reung , C. K. Williams . Highly active dizinc catalyst for the copolymerization of carbondioxide and cyclohexene oxide at one atmosphere pressure . Angew. Chem. Int. Ed. , 2009 . 48 931 - 933 . DOI: 10.1002/anie.v48:5 http://doi.org/10.1002/anie.v48:5 .

M. R. Kember , A. J. P. White , C. K. Williams . Di-and tri-zinc catalysts for the low-pressure copolymerization of CO 2 and cyclohexene oxide . Inorg. Chem. , 2009 . 48 9535 - 9542 . DOI: 10.1021/ic901109e http://doi.org/10.1021/ic901109e .

T. Ema , Y. Miyazaki , S. Koyama , Y. Yano , T. Sakai . A bifunctional catalyst for carbon dioxide fixation:cooperative double activation of epoxides for the synthesis of cyclic carbonates . Chem. Commun. , 2012 . 48 4489 - 4491 . DOI: 10.1039/c2cc30591g http://doi.org/10.1039/c2cc30591g .

J. E. Dengler , M. W. Lehenmeier , S. Klaus , C. E. Anderson , E. Herdtweck , B. Rieger . A one-component iron catalyst for cyclic propylene carbonate synthesis . Eur. J. Inorg. Chem. , 2011 . ( 3 ): 336 - 343 . https://www.researchgate.net/publication/264762652_A_One-Component_Iron_Catalyst_for_Cyclic_Propylene_Carbonate_Synthesis https://www.researchgate.net/publication/264762652_A_One-Component_Iron_Catalyst_for_Cyclic_Propylene_Carbonate_Synthesis , .

A. Buchard , M. R. Kember , K. G. Sandeman , C. K. Williams . A bimetallic iron(Ⅲ) catalyst for CO 2 /epoxide coupling . Chem. Commun. , 2011 . 47 212 - 214 . DOI: 10.1039/C0CC02205E http://doi.org/10.1039/C0CC02205E .

K. Nakano , K. Kobayashi , K. Nozaki . Tetravalent metal complexes as a new family of catalysts forcopolymerization of epoxides with carbon dioxide . J. Am. Chem. Soc. , 2011 . 133 10720 - 10723 . DOI: 10.1021/ja203382q http://doi.org/10.1021/ja203382q .

Y. Wang , Y. S. Qin , X. H. Wang , F. S. Wang . Trivalent titanium salen complex:thermally robust and highlyactive catalyst for copolymerization of CO 2 and cyclohexene oxide . ACS Catal. , 2015 . 393 - 396 . .

M. R. Kember , C. K. Williams . Efficient magnesium catalysts for the copolymerization of epoxidesand CO 2 ; using water to synthesize polycarbonate polyols . J. Am. Chem. Soc. , 2012 . 134 15676 - 15679 . DOI: 10.1021/ja307096m http://doi.org/10.1021/ja307096m .

K. Nakano , K. Kobayashi , T. Ohkawara , H. Imoto , K. Nozaki . Copolymerization of epoxides with carbon dioxide catalyzed by iron-corrole complexes:synthesis of a crystalline copolymer . J. Am. Chem. Soc. , 2013 . 135 8456 - 8459 . DOI: 10.1021/ja4028633 http://doi.org/10.1021/ja4028633 .

Y. L. Dong , X. H. Wang , X. J. Zhao , F. S. Wang . Facile synthesis of poly(ether carbonate)s via copolymerization of CO 2 and propylene oxide under combinatorial catalyst of rare earth ternary complex and double metal cyanide complex . J. Polym. Sci., Part A:Polym. Chem. , 2011 . 50 362 - 370 . https://www.researchgate.net/publication/257609186_Zinc_adipatetertiary_amine_catalytic_system_Efficient_synthesis_of_high_molecular_weight_polypropylene_carbonate https://www.researchgate.net/publication/257609186_Zinc_adipatetertiary_amine_catalytic_system_Efficient_synthesis_of_high_molecular_weight_polypropylene_carbonate , .

T. Aida , S. Inoue . Activation of carbon dioxide with aluminum porphyrin andreaction with epoxide. studies on(tetraphenylporphinato)aluminum alkoxide having a longoxyalkylene chain as the alkoxide group . J. Am. Chem. Soc. , 1983 . 105 1304 - 1309 . .

Y. S. Qin , X. H. Wang , S. B. Zhang , X. J. Zhao , F. S. Wang . Fixation of carbon dioxide into aliphatic polycarbonate, cobalt porphyrin catalyzed regio-specificpoly(propylene carbonate) with high molecular weight . J. Polym. Sci., Part A:Polym. Chem. , 2008 . 46 5959 - 5967 . DOI: 10.1002/pola.v46:17 http://doi.org/10.1002/pola.v46:17 .

W. Wu , X. F. Sheng , Y. S. Qin , L. J. Qiao , Y. Y. Miao , X. H. Wang , F. S. Wang . Bifunctional aluminum porphyrin complex:soil tolerant catalyst forcopolymerization of CO 2 and propylene oxide . J. Polym. Sci., Part A:Polym. Chem. , 2014 . 52 2346 - 2355 . DOI: 10.1002/pola.v52.16 http://doi.org/10.1002/pola.v52.16 .

C. Chatterjee , M. H. Chisholm . The Influence of the metal (Al, Cr, and Co) and the substituents of the porphyrin in controlling the reactions involved in the copolymerization of propylene oxide and carbon dioxide by porphyrin metal(Ⅲ) complexes. 1. aluminum chemistry . Inorg. Chem. , 2011 . 50 4481 - 4492 . https://www.researchgate.net/publication/256831616_Influence_of_the_Metal_Al_Cr_and_Co_and_the_Substituents_of_the_Porphyrin_in_Controlling_the_Reactions_Involved_in_the_Copolymerization_of_Propylene_Oxide_and_Carbon_Dioxide_by_Porphyrin_MetalIII_Comp https://www.researchgate.net/publication/256831616_Influence_of_the_Metal_Al_Cr_and_Co_and_the_Substituents_of_the_Porphyrin_in_Controlling_the_Reactions_Involved_in_the_Copolymerization_of_Propylene_Oxide_and_Carbon_Dioxide_by_Porphyrin_MetalIII_Comp , .

T. Ohkawara , K. Suzuki , K. Nakano , S. Mori , K. Nozaki . Facile estimation of catalytic activity and selectivities incopolymerization of propylene oxide with carbon dioxide mediatedby metal complexes with planar tetradentate ligand . J. Am. Chem. Soc. , 2014 . 136 10728 - 10735 . DOI: 10.1021/ja5046814 http://doi.org/10.1021/ja5046814 .

A. D. Adler , F. R. Longo , J. D. Finarelli , J. Goldmacher , J. Assour , L. Korsakoff . A simplified synthesis for meso-tetraphenylporphine . J. Org. Chem. , 1967 . 32 476 http://pubs.acs.org/doi/pdf/10.1021/jo01288a053 http://pubs.acs.org/doi/pdf/10.1021/jo01288a053 , .

R. L. Halterman , S. T. Jan . Catalytic asymmetric epoxidation of unfunctionalized alkenes using the 1 st D 4 -symmetrical metallotetraphenylporphyrin . J. Org. Chem. , 1991 . 56 5253 - 5254 . DOI: 10.1021/jo00018a008 http://doi.org/10.1021/jo00018a008 .

M. H. Chisholm , Z. P. Zhou . Concerning the mechanism of the ring opening of propylene oxide in the copolymerization of propylene oxide and carbon dioxide to give poly(propylene carbonate) . J. Am. Chem. Soc. , 2004 . 126 11030 - 11039 . DOI: 10.1021/ja0394232 http://doi.org/10.1021/ja0394232 .

M. H. Chisholm , D. Navarro-Llobet . NMR assignments of regioregular poly(propylene oxide) at the triad and tetrad level . Macromolecules , 2002 . 35 2389 - 2392 . DOI: 10.1021/ma0119934 http://doi.org/10.1021/ma0119934 .

X. B. Lu , Y. Wang . Highly active, binary catalyst systems for the alternating copolymerization of CO 2 and epoxides under mild conditions . Angew. Chem. Int. Ed. , 2004 . 43 3574 - 3577 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

C. T. Cohen , T. Chu , G. W. Coates . Cobalt catalysts for the alternating copolymerization of propylene oxide and carbon dioxide:combining high activity and selectivity . J. Am. Chem. Soc. , 2005 . 127 10869 - 10878 . DOI: 10.1021/ja051744l http://doi.org/10.1021/ja051744l .

W. M. Ren , W. Z Zhang , X. B. Lu . Highly regio-and stereo-selective copolymerization of CO 2 with racemic propylene oxide catalyzed by unsymmetrical (S, S, S)-salenCo(Ⅲ) complexes . Sci. China Chem. , 2010 . 53 1646 - 1652 . DOI: 10.1007/s11426-010-4049-1 http://doi.org/10.1007/s11426-010-4049-1 .

Y. S. Qin , L. J. Chen , X. H. Wang , X. J. Zhao , F. S. Wang . Alternating copolymerization of cyclohexene oxide and carbon sioxide under cobalt porphyrin catalyst . Chinese J. Polym. Sci. , 2011 . 29 602 - 608 . DOI: 10.1007/s10118-011-1073-3 http://doi.org/10.1007/s10118-011-1073-3 .

C. Chatterjee , M. H. Chisholm , A. El-Khaldy , R. D. McIntosh , J. T. Miller , T. Wu . Influence of the metal (Al, Cr, and Co) and substituents of the porphyrin in controlling reactions involved in copolymerization of propylene oxide and carbon dioxide by porphyrin metal(Ⅲ) complexes. 3. cobaltchemistry . Inorg. Chem. , 2013 . 52 4547 - 4553 . DOI: 10.1021/ic400068y http://doi.org/10.1021/ic400068y .

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Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO2 and Propylene Oxide

DOI：10.1007/s10118-018-2093-z

摘要

Abstract

关键词

Keywords

references

Steric Hindrance Ligand Strategy to Aluminum Porphyrin Catalyst for Completely Alternative Copolymerization of CO₂ and Propylene Oxide