Citation: Zhong-bao Jian. Synthesis of Functionalized Polyolefins: Design from Catalysts to Polar Monomers[J]. Acta Polymerica Sinica, ;2018, 0(11): 1359-1371. doi: 10.11777/j.issn1000-3304.2018.18146 shu

Synthesis of Functionalized Polyolefins: Design from Catalysts to Polar Monomers

Zhong-bao Jian ^,

State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022

Corresponding author: Zhong-bao Jian, zbjian@ciac.ac.cn
Received Date: 26 June 2018
Available Online: 6 September 2018

Coordination-insertion copolymerization of olefins and polar monomers for the preparation of functionalized polyolefins is one of the most important project in the field of olefin polymerization in the past twenty years. Due to the incorporation of functional groups, functionalized polyolefins, as the high value-added polymer materials, are of better surface properties and compatibility than those without any functionality, thus leading to expanding the range of applications. However, the presence of functional groups can also accelerate the chain transfer and chelate to the active central metal in the copolymerization of olefin and polar monomers, therefore this type of copolymerization suffers from lower catalytic activity and lower polymer molecular weight than the corresponding homo-polymerization of the olefins. As a result, the key for the high performance synthesis of functionalized polyolefins is to overcome the problem related to the functional groups of the polar monomers. In this Feature Article, recent research progress on the copolymerization of olefins and polar monomers to achieve the functionalized polyolefins by using late transition metal catalysts will be mostly summarized. Firstly, the milestone catalysts for the synthesis of functionalized polyolefins are introduced, and the latest research progresses on how to overcome the problem of polar monomer by designing nickel and palladium catalysts are highlighted. Then a series of our findings in recent years on the design of the polar monomers for the synthesis of functionalized polyolefins are revealed in detail, including the concept of polar di-vinyl monomers to overcome the problems related to polar monomers (rapid chain transfer reaction and chelation of functional group to active central metal) and the strategy of vinyl furan monomer with secondary coordination effect to synthesize novel functionalized polyolefins (telechelic polyolefin with two reactive endgroups). Finally, future development and long-standing challenges in the community of functionalized polyolefins by the copolymerization of olefins and polar monomers are out looked.
- Functionalized polyolefin,
- Late transition metal catalyst,
- Polar monomer,
- Coordination insertion polymerization,
- Catalytic activity and molecular weight
1. [1]
  Dong J Y, Hu Y L. Coord Chem Rev, 2006, 250(1-2): 47 − 65
2. [2]
  Boaen N K, Hillmyer M A. Chem Soc Rev, 2005, 34(3): 267 − 275
3. [3]
  Franssen N M G, Reek J N H, de Bruin B. Chem Soc Rev, 2013, 42(13): 5809 − 5832
4. [4]
  Boffa L S, Novak B M. Chem Rev, 2000, 100(4): 1479 − 1494
5. [5]
  Chen E Y X. Chem Rev, 2009, 109(11): 5157 − 5214
6. [6]
  Nakamura A, Ito S, Nozaki K. Chem Rev, 2009, 109(11): 5215 − 5244
7. [7]
  Nakamura A, Anselment T M J, Claverie J, Goodall B, Jordan R F, Mecking S, Rieger B, Sen A, van Leeuwen P W N M, Nozaki K. Acc Chem Res, 2013, 46(7): 1438 − 1449
8. [8]
  Terao H, Ishii S, Mitani M, Tanaka H, Fujita T. J Am Chem Soc, 2008, 130(52): 17636 − 17637
9. [9]
  Yang X, Liu C, Wang C, Sun X, Guo Y, Wang X, Wang Z, Xie Z, Tang Y. Angew Chem Int Ed, 2009, 48(43): 8099 − 8102
10. [10]
  Chen Z, Li J, Tao W, Sun X, Yang X, Tang Y. Macromolecules, 2013, 46(7): 2870 − 2875
11. [11]
  Wang X Y, Wang Y, Shi X C, Liu J Y, Chen C L, Li Y S. Macromolecules, 2014, 47(2): 552 − 559
12. [12]
  Liu D T, Yao C G, Wang R, Wang M Y, Wang Z C, Wu C J, Lin F, Li S H, Wan X H, Cui D M. Angew Chem Int Ed, 2015, 54(17): 5205 − 5209
13. [13]
  Liu D T, Wang M Y, Wang Z C, Wu C J, Pan Y P, Cui D M. Angew Chem Int Ed, 2017, 56(10): 2714 − 2719
14. [14]
  Wang C X, Luo G, Nishiura M, Song G Y, Yamamoto A, Luo Y, Hou Z M. Sci Adv, 2017, 3(7): e1701011
15. [15]
16. [16]
  Chen J, Gao Y, Wang B, Lohr T L, Marks T J. Angew Chem Int Ed, 2017, 56(50): 15964 − 15968
17. [17]
  Keim W, Kowaldt F H, Goddard R, Krüger C. Angew Chem Int Ed Engl, 1978, 17(6): 466 − 467
18. [18]
  Johnson, L K, Mecking S, Brookhart M. J Am Chem Soc, 1996, 118(1): 267 − 268
19. [19]
  Drent E, van Dijk R, van Ginkel R, van Oort B, Pugh R I. Chem Commun, 2002: 744 − 745
20. [20]
  Camacho D H, Salo E V, Ziller J W, Guan Z. Angew Chem Int Ed, 2004, 43(14): 1821 − 1825
21. [21]
  Popeney C S, Camacho D H, Guan Z. J Am Chem Soc, 2007, 129(33): 10062 − 10063
22. [22]
  Vaidya T, Klimovica K, LaPointe A M, Keresztes I, Lobkovsky E B, Daugulis O, Coates G W. J Am Chem Soc, 2014, 136(20): 7213 − 7216
23. [23]
  Allen K E, Campos J, Daugulis O, Brookhart M. ACS Catal, 2015, 5(1): 456 − 464
24. [24]
  Rhinehart J L, Brown L A, Long B K. J Am Chem Soc, 2013, 135(44): 16316 − 16319
25. [25]
  Dai S Y, Sui X L, Chen C L. Angew Chem Int Ed, 2015, 54(34): 9948 − 9953
26. [26]
  Dai S Y, Chen C L. Angew Chem Int Ed, 2016, 55(42): 13281 − 13285
27. [27]
  Long B K, Eagan J M, Mulzer M, Coates G W. Angew Chem Int Ed, 2016, 55(25): 7106 − 7110
28. [28]
  Zhong L, Li G, Liang G, Gao H, Wu Q. Macromolecules, 2017, 50(7): 2675 − 2682
29. [29]
  Zhong S, Tan Y, Zhong L, Gao J, Liao H, Jiang L, Gao H, Wu Q. Macromolecules, 2017, 50(15): 5661 − 5669
30. [30]
  Guo L, Gao H, Guan Q, Hu H, Deng J, Liu J, Liu F, Wu Q. Organometallics, 2012, 31(17): 6054 − 6062
31. [31]
  Skupov K M, Marella P R, Simard M, Yap G P A, Allen N, Conner D, Goodall B L, Claverie J P. Macromol Rapid Commun, 2007, 28(20): 2033 − 2038
32. [32]
  Guironnet D, Roesle P, Rünzi T, Göttker-Schnetmann I, Mecking S. J Am Chem Soc, 2009, 131(2): 422 − 423
33. [33]
  Neuwald B, Caporaso L, Cavallo L, Mecking S. J Am Chem Soc, 2013, 135(3): 1026 − 1036
34. [34]
  Wucher P, Goldbach V, Mecking S. Organometallics, 2013, 32(16): 4516 − 4522
35. [35]
  Ota Y, Ito S, Kuroda J, Okumura Y, Nozaki K. J Am Chem Soc, 2014, 136(34): 11898 − 11901
36. [36]
  Chen M, Chen C L. ACS Catal, 2017, 7(2): 1308 − 1312
37. [37]
  Carrow B P, Nozaki K. J Am Chem Soc, 2012, 134(21): 8802 − 8805
38. [38]
  Xin B S, Sato N, Tanna A, Oishi Y, Konishi Y, Shimizu F. J Am Chem Soc, 2017, 139(10): 3611 − 3614
39. [39]
  Chen M, Chen C L. Angew Chem Int Ed, 2018, 57(12): 3094 − 3098
40. [40]
  Mitsushige Y, Yasuda H, Carrow B P, Ito S, Kobayashi M, Tayano T, Watanabe Y, Okuno Y, Hayashi S, Kuroda J, Okumura Y, Nozaki K. ACS Macro Lett, 2018, 7(3): 305 − 311
41. [41]
  Zhang Y P, Mu H L, Pan L, Wang X L, Li Y S. ACS Catal, 2018, 8: 5963 − 5976
42. [42]
  Yasuda H, Nakano R, Ito S, Nozaki K. J Am Chem Soc, 2018, 140(10): 1876 − 1883
43. [43]
  Chen Z, Liu W, Daugulis O, Brookhart M. J Am Chem Soc, 2016, 138(49): 16120 − 16129
44. [44]
  Chen Z, Leatherman M D, Daugulis O, Brookhart M. J Am Chem Soc, 2017, 139(44): 16013 − 16022
45. [45]
  Radlauer M R, Buckley A K, Henling L M, Agapie T. J Am Chem Soc, 2013, 135(10): 3784 − 3787
46. [46]
  Takeuchi D, Chiba Y, Takano S, Osakada K. Angew Chem Int Ed, 2013, 52(48): 12536 − 12540
47. [47]
  Takano S, Takeuchi D, Osakada K, Akamatsu N, Shishido A. Angew Chem Int Ed, 2014, 53(35): 9246 − 9250
48. [48]
  Li M, Wang X B, Luo Y, Chen C L. Angew Chem Int Ed, 2017, 56(38): 11604 − 11609
49. [49]
  Zhang D, Chen C L. Angew Chem Int Ed, 2017, 56(46): 14672 − 14676
50. [50]
  Chen M, Yang B P, Chen C L. Angew Chem Int Ed, 2015, 54(51): 15520 − 15524
51. [51]
  Mu H L, Pan L, Song D P, Li Y S. Chem Rev, 2015, 115(22): 12091 − 12137
52. [52]
  Guo L H, Liu W J, Chen C L. Mater Chem Front, 2017, 1(12): 2487 − 2494
53. [53]
  Chen C L. Nat Rev Chem, 2018, 2(5): 6 − 14
54. [54]
  Chen C L. ACS Catal, 2018, 8(6): 5506 − 5514
55. [55]
  Daigle J C, Piche L, Arnold A, Claverie J P. ACS Macro Lett, 2012, 1(3): 343 − 346
56. [56]
  Rünzi T, Guironnet D, Göttker-Schnetmann I, Mecking S. J Am Chem Soc, 2010, 132(46): 16623 − 16630
57. [57]
  Jian Z, Baier M C, Mecking S. J Am Chem Soc, 2015, 137(8): 2836 − 2839
58. [58]
  Jian Z, Mecking S. Angew Chem Int Ed, 2015, 54(52): 15845 − 15849
59. [59]
  Wimmer F P, Caporaso L, Cavallo L, Mecking S, Falivene L. Macromolecules, 2018, 51(12): 4525 − 4531
60. [60]
  Luo S, Vela J, Lief G R, Jordan R F. J Am Chem Soc, 2007, 129(29): 8946 − 8947
61. [61]
  Chen C L, Luo S, Jordan R F. J Am Chem Soc, 2010, 132(14): 5273 − 5284
62. [62]
  Jian Z, Mecking S. Macromolecules, 2016, 49(42): 4395 − 4403
63. [63]
  Jian Z, Falivene L, Boffa G, Ortega Sánchez S, Caporaso L, Grassi A, Mecking S. Angew Chem Int Ed, 2016, 55(46): 14378 − 14383
64. [64]
  Dai S Y, Zhou S X, Zhang W, Chen C L. Macromolecules, 2016, 49(23): 8855 − 8862
65. [65]
  Na Y N, Dai S Y, Chen C L. Macromolecules, 2018, 51(12): 4040 − 4048
1. [1]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
2. [2]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
3. [3]
  Fangxuan Liu , Ziyan Liu , Guowei Zhou , Tingting Gao , Wenyu Liu , Bin Sun . Hollow structured photocatalysts. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-. doi: 10.1016/j.actphy.2025.100071
4. [4]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
5. [5]
  Xueqi Yang , Juntao Zhao , Jiawei Ye , Desen Zhou , Tingmin Di , Jun Zhang . 调节NNU-55(Fe)的d带中心以增强CO₂吸附和光催化活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100074-. doi: 10.1016/j.actphy.2025.100074
6. [6]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
7. [7]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
8. [8]
  Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . 具有富电子Pt^δ^-壳层的空心AgPt@Pt核壳催化剂：提升光催化H₂O₂生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-. doi: 10.1016/j.actphy.2025.100081
9. [9]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
10. [10]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
11. [11]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
12. [12]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
13. [13]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
14. [14]
  Yuchen Zhou , Huanmin Liu , Hongxing Li , Xinyu Song , Yonghua Tang , Peng Zhou . Designing thermodynamically stable noble metal single-atom photocatalysts for highly efficient non-oxidative conversion of ethanol into high-purity hydrogen and value-added acetaldehyde. Acta Physico-Chimica Sinica, 2025, 41(6): 100067-. doi: 10.1016/j.actphy.2025.100067
15. [15]
  Pingping Zhu , Qiang Zhou , Yu Huang , Haiyang Yang , Pingsheng He , Shiyan Xiao . Design and Practice of Ideological and Political Cases in the Course of Polymer Physics Experiments: Molecular Weight Determination of Polymers by Dilute Solution Viscosity Method as an Example. University Chemistry, 2025, 40(4): 94-99. doi: 10.12461/PKU.DXHX202405170
16. [16]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
17. [17]
  Lilong Gao , Yuhao Zhai , Dongdong Zhang , Linjun Huang , Kunyan Sui . Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching. University Chemistry, 2025, 40(4): 87-93. doi: 10.12461/PKU.DXHX202405143
18. [18]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
19. [19]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
20. [20]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(134)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142