Citation: Chun-Wei Zhuo, Yu-Sheng Qin, Xian-Hong Wang, Fo-Song Wang. 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 shu

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

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

Corresponding author: Yu-Sheng Qin, ysqin@ciac.ac.cn Xian-Hong Wang, xhwang@ciac.ac.cn
Received Date: 6 November 2017
Accepted Date: 15 November 2017
Available Online: 29 November 2017

Aluminum porphyrin complexes are heavy-metal-free and soil-tolerant green catalysts for the copolymerization of CO₂ 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, 10, 15, 20-tetra(1, 2, 3, 4, 5, 6, 7, 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.
- Carbon dioxide,
- Propylene oxide,
- Porphyrin,
- Aluminum,
- Steric hindrance
1. [1]
  Inoue S, Koinuma H, Tsuruta T. Copolymerization of carbon dioxide and epoxide with organometallic compounds[J]. Makromol. Chem., 1969,130:210-220. doi: 10.1002/macp.1969.021300112
2. [2]
  Inoue S, Koinuma H, Tsuruta T. Copolymerization of carbon dioxide and epoxide[J]. J. Polym. Sci., Part B:Polym. Lett., 1969,7:287-292. doi: 10.1002/pol.1969.110070408
3. [3]
  Liu B. Y., Zhao X. J., Wang X. H., Wang F. S.. Copolymerization of carbon dioxide and propylene oxidewith Ln(CCl₃COO)₃-based catalyst:the role of rare-earth compound in the catalytic system[J]. J. Polym. Sci., Part A:Polym. Chem., 2001,39:2751-2754.
4. [4]
  Quan Z. L., Wang X. H., Zhao X. J., Wang F. S.. Copolymerization of CO₂ and propylene oxide under rare earth ternarycatalyst:design of ligand in yttrium complex[J]. Polymer, 2003,44:5605-5610. doi: 10.1016/S0032-3861(03)00561-5
5. [5]
  Paddock R. L., Nguyen S. T.. Chemical CO₂ fixation:Cr(Ⅲ) salen complexes as highly efficient catalysts for the coupling of CO₂ and epoxides[J]. J. Am. Chem. Soc., 2001,123:11498-11499. doi: 10.1021/ja0164677
6. [6]
  Darensbourg D. J., Yarbrough J. C.. Mechanistic aspects of the copolymerization reaction of carbon dioxide and epoxides, using a chiral salen chromium chloride catalyst[J]. J. Am. Chem. Soc., 2002,124:6335-6342. doi: 10.1021/ja012714v
7. [7]
  Darensbourg D. J., Yarbrough J. C., Ortiz C., Fang C. C.. 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]. J. Am. Chem. Soc., 2003,125:7586-7591.
8. [8]
  Qin Z.Q., Thomas C. M., Lee S., Coates G. W.. Cobalt-based complexes for the copolymerization of propylene oxide and CO₂:active and selective catalysts for polycarbonate synthesis[J]. Angew. Chem. Int. Ed., 2003,42:5484-5487. doi: 10.1002/(ISSN)1521-3773
9. [9]
  Nakano K., Kamada T., Nozaki K.. Selective formation of polycarbonate over cyclic carbonate:copolymerization of epoxides with carbon dioxide catalyzed by a cobalt(Ⅲ) complex with a piperidiniumend-capping arm[J]. Angew. Chem. Int. Ed., 2006,45:7274-7277. doi: 10.1002/(ISSN)1521-3773
10. [10]
  Ren W. M., Liu Z. W., Wen Y. Q., Zhang R., Lu X. B.. Mechanistic aspects of the copolymerization of CO₂ withepoxides using a thermally stable single-site cobalt(Ⅲ)catalyst[J]. J. Am. Chem. Soc., 2009,131:11509-11518. doi: 10.1021/ja9033999
11. [11]
  Noh E. K., Na S. J., Sujith S., Kim S. W., Lee B. Y.. Two components in a molecule:highly efficient and thermally robust catalytic system for CO₂/epoxide copolymerization[J]. J. Am. Chem. Soc., 2007,129:8082-8083. doi: 10.1021/ja071290n
12. [12]
  Sujith S., Min J. K., Seong J. E., Na S. J., Lee B. Y.. A highly active and recyclable catalytic system for CO₂/propylene oxide copolymerization[J]. Angew. Chem. Int. Ed., 2008,47:7306-7309. doi: 10.1002/anie.v47:38
13. [13]
  Na S. J., Sujith S., Cyriac A., Kim B. E., Yoo J., Kang Y. K., Han S. J., Lee C., Lee B. Y.. Elucidation of the structure of a highly active catalytic system for CO₂/epoxide copolymerization:a salen-cobaltate complex of an unusual binding mode[J]. Inorg. Chem., 2009,48:10455-10465. doi: 10.1021/ic901584u
14. [14]
  Cyriac A., Jeon J. Y., Varghese J. K., Park J. H., Choi S. Y., Chung Y. K., Lee B. Y.. Unusual coordination mode of tetradentate Schiff base cobalt(Ⅲ) complexes[J]. Dalton Trans., 2012,41:1444-1447. doi: 10.1039/C2DT11871H
15. [15]
  Takeda N, Inoue S.. Polymerization of 1, 2-epoxypropane and copolymerizationwith carbon dioxide catalyzed by metalloporphyrins[J]. Makromol Chem., 1978,179:1377-1381. doi: 10.1002/macp.1978.021790529
16. [16]
  Darensbourg D. J., Billodeaux D. R.. Aluminum salen complexes and tetrabutylammonium salts:abinary catalytic system for production of polycarbonates from CO₂ and cyclohexene oxide[J]. Inorg. Chem., 2005,44:1433-1442. doi: 10.1021/ic048508g
17. [17]
  Kember M. R., Knight P. D., Reung P. T. R., Williams C. K.. Highly active dizinc catalyst for the copolymerization of carbondioxide and cyclohexene oxide at one atmosphere pressure[J]. Angew. Chem. Int. Ed., 2009,48:931-933. doi: 10.1002/anie.v48:5
18. [18]
  Kember M. R., White A. J. P., Williams C. K.. Di-and tri-zinc catalysts for the low-pressure copolymerization of CO₂ and cyclohexene oxide[J]. Inorg. Chem., 2009,48:9535-9542. doi: 10.1021/ic901109e
19. [19]
  Ema T., Miyazaki Y., Koyama S., Yano Y., Sakai T.. A bifunctional catalyst for carbon dioxide fixation:cooperative double activation of epoxides for the synthesis of cyclic carbonates[J]. Chem. Commun., 2012,48:4489-4491. doi: 10.1039/c2cc30591g
20. [20]
  Dengler J. E., Lehenmeier M. W., Klaus S., Anderson C. E., Herdtweck E., Rieger B.. A one-component iron catalyst for cyclic propylene carbonate synthesis[J]. Eur. J. Inorg. Chem., 2011(3):336-343.
21. [21]
  Buchard A., Kember M. R., Sandeman K. G., Williams C. K.. A bimetallic iron(Ⅲ) catalyst for CO₂/epoxide coupling[J]. Chem. Commun., 2011,47:212-214. doi: 10.1039/C0CC02205E
22. [22]
  Nakano K., Kobayashi K., Nozaki K.. Tetravalent metal complexes as a new family of catalysts forcopolymerization of epoxides with carbon dioxide[J]. J. Am. Chem. Soc., 2011,133:10720-10723. doi: 10.1021/ja203382q
23. [23]
  Wang Y., Qin Y. S., Wang X. H., Wang F. S.. Trivalent titanium salen complex:thermally robust and highlyactive catalyst for copolymerization of CO₂ and cyclohexene oxide[J]. ACS Catal., 2015:393-396.
24. [24]
  Kember M. R., Williams C. K.. Efficient magnesium catalysts for the copolymerization of epoxidesand CO₂; using water to synthesize polycarbonate polyols[J]. J. Am. Chem. Soc., 2012,134:15676-15679. doi: 10.1021/ja307096m
25. [25]
  Nakano K., Kobayashi K., Ohkawara T., Imoto H., Nozaki K.. Copolymerization of epoxides with carbon dioxide catalyzed by iron-corrole complexes:synthesis of a crystalline copolymer[J]. J. Am. Chem. Soc., 2013,135:8456-8459. doi: 10.1021/ja4028633
26. [26]
  Dong Y. L., Wang X. H., Zhao X. J., Wang F. S.. Facile synthesis of poly(ether carbonate)s via copolymerization of CO₂ and propylene oxide under combinatorial catalyst of rare earth ternary complex and double metal cyanide complex[J]. J. Polym. Sci., Part A:Polym. Chem., 2011,50:362-370.
27. [27]
  Aida T., Inoue S.. Activation of carbon dioxide with aluminum porphyrin andreaction with epoxide. studies on(tetraphenylporphinato)aluminum alkoxide having a longoxyalkylene chain as the alkoxide group[J]. J. Am. Chem. Soc., 1983,105:1304-1309.
28. [28]
  Qin Y. S., Wang X. H., Zhang S. B., Zhao X. J., Wang F. S.. Fixation of carbon dioxide into aliphatic polycarbonate, cobalt porphyrin catalyzed regio-specificpoly(propylene carbonate) with high molecular weight[J]. J. Polym. Sci., Part A:Polym. Chem., 2008,46:5959-5967. doi: 10.1002/pola.v46:17
29. [29]
  Wu W., Sheng X. F., Qin Y. S., Qiao L. J., Miao Y. Y., Wang X. H., Wang F. S.. Bifunctional aluminum porphyrin complex:soil tolerant catalyst forcopolymerization of CO₂ and propylene oxide[J]. J. Polym. Sci., Part A:Polym. Chem., 2014,52:2346-2355. doi: 10.1002/pola.v52.16
30. [30]
  Chatterjee C., Chisholm M. H.. 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[J]. Inorg. Chem., 2011,50:4481-4492.
31. [31]
  Ohkawara T., Suzuki K., Nakano K., Mori S., Nozaki K.. Facile estimation of catalytic activity and selectivities incopolymerization of propylene oxide with carbon dioxide mediatedby metal complexes with planar tetradentate ligand[J]. J. Am. Chem. Soc., 2014,136:10728-10735. doi: 10.1021/ja5046814
32. [32]
  Adler A. D., Longo F. R., Finarelli J. D., Goldmacher J., Assour J., Korsakoff L.. A simplified synthesis for meso-tetraphenylporphine[J]. J. Org. Chem., 1967,32476.
33. [33]
  Halterman R. L., Jan S. T.. Catalytic asymmetric epoxidation of unfunctionalized alkenes using the 1^st D₄-symmetrical metallotetraphenylporphyrin[J]. J. Org. Chem., 1991,56:5253-5254. doi: 10.1021/jo00018a008
34. [34]
  Chisholm M. H., Zhou Z. P.. 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]. J. Am. Chem. Soc., 2004,126:11030-11039. doi: 10.1021/ja0394232
35. [35]
  Chisholm M. H., Navarro-Llobet D.. NMR assignments of regioregular poly(propylene oxide) at the triad and tetrad level[J]. Macromolecules, 2002,35:2389-2392. doi: 10.1021/ma0119934
36. [36]
  Lu X. B., Wang Y.. Highly active, binary catalyst systems for the alternating copolymerization of CO₂ and epoxides under mild conditions[J]. Angew. Chem. Int. Ed., 2004,43:3574-3577. doi: 10.1002/(ISSN)1521-3773
37. [37]
  Cohen C. T., Chu T., Coates G. W.. Cobalt catalysts for the alternating copolymerization of propylene oxide and carbon dioxide:combining high activity and selectivity[J]. J. Am. Chem. Soc., 2005,127:10869-10878. doi: 10.1021/ja051744l
38. [38]
  Ren W. M., Zhang W. Z, Lu X. B.. Highly regio-and stereo-selective copolymerization of CO₂ with racemic propylene oxide catalyzed by unsymmetrical (S, S, S)-salenCo(Ⅲ) complexes[J]. Sci. China Chem., 2010,53:1646-1652. doi: 10.1007/s11426-010-4049-1
39. [39]
  Qin Y. S., Chen L. J., Wang X. H., Zhao X. J., Wang F. S.. Alternating copolymerization of cyclohexene oxide and carbon sioxide under cobalt porphyrin catalyst[J]. Chinese J. Polym. Sci., 2011,29:602-608. doi: 10.1007/s10118-011-1073-3
40. [40]
  Chatterjee C., Chisholm M. H., El-Khaldy A., McIntosh R. D., Miller J. T., Wu T.. 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[J]. Inorg. Chem., 2013,52:4547-4553. doi: 10.1021/ic400068y
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沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

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