Download PDF
CC BY-NC-ND 4.0 · Organic Materials 2022; 4(04): 178-189
DOI: 10.1055/a-1945-0777
Emerging Stars in Organic and Polymer Materials
Short Review

Stereoselective Copolymerization of Olefin with Polar Monomers to Access Stereoregular Functionalized Polyolefins

Hongliang Mu 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Renmin Street 5625, Changchun 130022, P. R. of China
,
Zhongbao Jian 
a   State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Renmin Street 5625, Changchun 130022, P. R. of China
b   University of Science and Technology of China, Hefei 230026, P. R. of China
› Author Affiliations
› Further Information
   Permissions and Reprints All articles of this category


Abstract

Introducing polar functionalities to polyolefins such as polyethylene and polypropylene is highly desirable for improving physical properties of the otherwise non-polar material. The synthesis of stereoregular functionalized polyolefins, however, has been a relatively underdeveloped area compared to that of functionalized polyethylene because of the lack of suitable catalysts that tolerate polar groups while possessing stereoselectivity. This review summarizes recent advances concerning the access to stereoregular functionalized polyolefins, including synthetic strategies such as post-functionalization, chain transfer and direct copolymerization methods. The focus of the review lies in the copolymerization approach, in which various polar comonomers and versatile stereoselective polymerization catalysts based on both early and late transition metals are involved. Polymer properties and potential applications for these materials are simply discussed.

1. Introduction

2. Reactive-Intermediate-Polymer Approach to Stereoregular Functionalized Polypropylene

3. Preparation of Stereoregular Functionalized Polypropylene by Chain-End Functionalization

4. Stereoselective Copolymerization of Propylene and Polar Monomers by Early Transition Metal Catalysts

5. Stereoselective Copolymerization of Propylene with Polar Monomers by Late Transition Metal Catalysts

6. Stereoselective Copolymerization of α-Olefins with Polar Monomers

7. Stereoselective Homopolymerization of Polar Monomers

8. Polymer Properties and Potential Applications

9. Conclusion and Outlook

Key words

polypropylene - isotactic - stereoregularity - functionalized polyolefins - stereoselective polymerization - poly(α-olefin)s


Publication History

Received: 11 August 2022

Accepted after revision: 12 September 2022

Accepted Manuscript online:
15 September 2022

Article published online:
26 October 2022

© 2022. The authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 2 Worch JC, Prydderch H, Jimaja S, Bexis P, Becker ML, Dove AP. Nat. Rev. Chem. 2019; 3: 514
    CrossrefPubMed
    • 3a Biroš J, Larina T, Trekoval J, Pouchlý J. Colloid Polym. Sci. 1982; 260: 27
      CrossrefPubMed
    • 3b Fox TG, Garrett BS, Goode WE, Gratch S, Kincaid JF, Spell A, Stroupe JD. J. Am. Chem. Soc. 1958; 80: 1768
      CrossrefPubMed
    • 4a Tschan MJ, Gauvin RM, Thomas CM. Chem. Soc. Rev. 2021; 50: 13587
      CrossrefPubMed
    • 4b Stanford MJ, Dove AP. Chem. Soc. Rev. 2010; 39: 486
      CrossrefPubMed
    • 5a Varner TP, Teator AJ, Reddi Y, Jacky PE, Cramer CJ, Leibfarth FA. J. Am. Chem. Soc. 2020; 142: 17175
      CrossrefPubMed
    • 5b Teator AJ, Leibfarth FA. Science 2019; 363: 1439
      CrossrefPubMed
    • 6a Walters AJ, Troeppner O, Ivanovic-Burmazovic I, Tejel C, del Rio MP, Reek JN, de Bruin B. Angew. Chem. Int. Ed. 2012; 51: 5157
      CrossrefPubMed
    • 6b Hetterscheid DG, Hendriksen C, Dzik WI, Smits JM, van Eck ER, Rowan AE, Busico V, Vacatello M, Van Axel Castelli V, Segre A, Jellema E, Bloemberg TG, de Bruin B. J. Am. Chem. Soc. 2006; 128: 9746
      CrossrefPubMed
  • 7 Coates GW. Chem. Rev. 2000; 100: 1223
    CrossrefPubMed
  • 9 Williamson JB, Lewis SE, Johnson III RR, Manning IM, Leibfarth FA. Angew. Chem. Int. Ed. 2019; 58: 8654
    CrossrefPubMed
  • 11 Resconi L, Cavallo L, Fait A, Piemontesi F. Chem. Rev. 2000; 100: 1253
    CrossrefPubMed
  • 12 Woo EM, Chang L. Tacticity in Vinyl Polymers.. Encyclopedia of Polymer Science and Technology. New Jersey: John Wiley & Sons, Ltd.; 2011
    Google Scholar
  • 13 Chung TCM. Macromol. React. Eng. 2014; 8: 69
    CrossrefPubMed
    • 14a Chung TC. Functionalized Polyolefins via Copolymerization of Borane Monomers in Ziegler-Natta Process.. Advances in New Materials. Dordrecht: Springer; 1992: 323
      Google Scholar
    • 14b Chung TC. Macromol. Symp. 1995; 89: 151
      CrossrefPubMed
    • 14c Zou J, Cao C, Dong J, Hu Y, Chung TC. Macromol. Rapid Commun. 2004; 25: 1797
      CrossrefPubMed
  • 15 Chung TC, Rhubright D, Jiang GJ. Macromolecules 1993; 26: 3467
    CrossrefPubMed
  • 16 Chung TC, Rhubright D. Macromolecules 1994; 27: 1313
    CrossrefPubMed
  • 17 López-Barrón CR, Lambic NS, Throckmorton JA, Schaefer JJ, Smith A, Raushel FN, Lin T-P. Macromolecules 2022; 55: 284
    CrossrefPubMed
  • 18 Dong C, Wang N, Qin Y, Niu H, Dong J. Macromol. Chem. Phys. 2014; 215: 1776
    CrossrefPubMed
  • 19 Wang X, Wang Y, Li Y, Pan L. Macromolecules 2015; 48: 1991
    CrossrefPubMed
  • 20 Zhang D, Pan L, Li Y, Wang B, Li Y. Macromolecules 2017; 50: 2276
    CrossrefPubMed
  • 21 Li Y, Song D, Pan L, Ma Z, Li Y. Polym. Chem. 2019; 10: 6368
    CrossrefPubMed
  • 22 Doi Y, Suzuki S, Soga K. Macromolecules 1986; 19: 2896
    CrossrefPubMed
  • 24 Lin W, Dong J, Chung TCM. Macromolecules 2008; 41: 8452
    CrossrefPubMed
    • 25a Shiono T, Soga K. Macromolecules 1992; 25: 3356
      CrossrefPubMed
    • 25b Shiono T, Yoshida K, Soga K. Makromol. Chem. Rapid Commun. 1990; 11: 169
      CrossrefPubMed
    • 25c Kuo JC, Lin WF, Yu CH, Tsai JC, Wang TC, Chung TM, Ho RM. Macromolecules 2008; 41: 7967
      CrossrefPubMed
    • 25d Ye Y, Li P, Shangguan Y, Fu Z, Zheng Q, Fan Z. Chin. Chem. Lett. 2014; 25: 596
      CrossrefPubMed
  • 26 Fan G, Dong J. J. Mol. Catal. A: Chem. 2005; 236: 246
    CrossrefPubMed
    • 27a Huang H, Cao C, Niu H, Dong J. J. Polym. Sci., Part A: Polym. Chem. 2010; 48: 3709
      CrossrefPubMed
    • 27b Dong J, Wang Z, Hong H, Chung TC. Macromolecules 2002; 35: 9352
      CrossrefPubMed
  • 28 Chung TC. J. Organomet. Chem. 2005; 690: 6292
    CrossrefPubMed
  • 29 Lee JY, Tsai JC. J. Polym. Sci., Part A: Polym. Chem. 2011; 49: 3739
    CrossrefPubMed
  • 30 Lin W-F, Tsai J-C. J. Polym. Sci., Part A: Polym. Chem. 2008; 46: 2167
    CrossrefPubMed
  • 31 Yan T, Guironnet D. Angew. Chem. Int. Ed. 2020; 59: 22983
    CrossrefPubMed
  • 32 Stehling UM, Malmström EE, Waymouth RM, Hawker CJ. Macromolecules 1998; 31: 4396
    CrossrefPubMed
  • 33 Hagihara H, Tsuchihara K, Sugiyama J, Takeuchi K, Shiono T. Macromolecules 2004; 37: 5145
    CrossrefPubMed
  • 34 Hagihara H, Ishihara T, The Ban H, Shiono T. J. Polym. Sci., Part A: Polym. Chem. 2008; 46: 1738
    CrossrefPubMed
  • 35 Zhao P, Shpasser D, Eisen MS. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 523
    CrossrefPubMed
  • 36 Tanaka R, Fujii H, Kida T, Nakayama Y, Shiono T. Macromolecules 2021; 54: 1267
    CrossrefPubMed
  • 37 Zhang G, Li H, Antensteiner M, Chung TCM. Macromolecules 2015; 48: 2925
    CrossrefPubMed
  • 38 Kawahara N, Saito J, Matsuo S, Kaneko H, Matsugi T, Kojoh S-i, Kashiwa N. Polym. Bull. 2007; 59: 177
    CrossrefPubMed
    • 39a Wang X, Wang Y, Shi X, Liu J, Chen C, Li Y. Macromolecules 2014; 47: 552
      CrossrefPubMed
    • 39b Wang X, Li Y, Mu H, Pan L, Li Y. Polym. Chem. 2015; 6: 1150
      CrossrefPubMed
  • 40 Wang X, Long Y, Wang Y, Li Y. J. Polym. Sci., Part A: Polym. Chem. 2014; 52: 3421
    CrossrefPubMed
  • 41 Shang R, Gao H, Li Y, Wang B, Ma Z, Pan L, Li Y. Acta Polym. Sin. 2019; 50: 1187
    CrossrefPubMed
  • 42 Shang R, Gao H, Luo F, Li Y, Wang B, Ma Z, Pan L, Li Y. Macromolecules 2019; 52: 9280
    CrossrefPubMed
  • 43 Zhang M, Yuan X, Wang L, Chung TCM, Huang T, deGroot W. Macromolecules 2014; 47: 571
    CrossrefPubMed
  • 44 Huang M, Chen J, Wang B, Huang W, Chen H, Gao Y, Marks TJ. Angew. Chem. Int. Ed. 2020; 59: 20522
    CrossrefPubMed
  • 45 Weiss RA, Agarwal PK. J. Appl. Polym. Sci. 1981; 26: 449
    CrossrefPubMed
  • 46 Landoll LM, Breslow DS. J. Polym. Sci., Part A: Polym. Chem. 1989; 27: 2189
    CrossrefPubMed
  • 47 Dassaud JP, Gallot B, Guyot A, Spitz R, Beautemps JP, Williams C, Bourgaux C, Eisenberg A. Polym. Adv. Technol. 1994; 5: 79
    CrossrefPubMed
  • 48 Meng Q, Wang B, Pan L, Li Y, Ma Z. Acta Polym. Sin. 2017; 1762
    PubMed
  • 49 Luckham SLJ, Nozaki K. Acc. Chem. Res. 2021; 54: 344
    CrossrefPubMed
  • 50 Johnson LK, Mecking S, Brookhart M. J. Am. Chem. Soc. 1996; 118: 267
    CrossrefPubMed
    • 51a Cherian AE, Rose JM, Lobkovsky EB, Coates GW. J. Am. Chem. Soc. 2005; 127: 13770
      CrossrefPubMed
    • 51b Rose JM, Deplace F, Lynd NA, Wang Z, Hotta A, Lobkovsky EB, Kramer EJ, Coates GW. Macromolecules 2008; 41: 9548
      CrossrefPubMed
  • 52 Nakano R, Nozaki K. J. Am. Chem. Soc. 2015; 137: 10934
    CrossrefPubMed
  • 53 Park DA, Byun S, Ryu JY, Lee J, Lee J, Hong S. ACS Catal. 2020; 10: 5443
    CrossrefPubMed
  • 54 Ota Y, Ito S, Kobayashi M, Kitade S, Sakata K, Tayano T, Nozaki K. Angew. Chem. Int. Ed. 2016; 55: 7505
    CrossrefPubMed
  • 55 Chen Z, Zhao X, Gong X, Xu D, Ma Y. Macromolecules 2017; 50: 6561
    CrossrefPubMed
  • 56 Seidel FW, Tomizawa I, Nozaki K. Angew. Chem. Int. Ed. 2020; 59: 22591
    CrossrefPubMed
  • 57 Konishi Y, Tao W-j, Yasuda H, Ito S, Oishi Y, Ohtaki H, Tanna A, Tayano T, Nozaki K. ACS Macro Lett. 2018; 7: 213
    CrossrefPubMed
  • 58 Jung J, Yasuda H, Nozaki K. Macromolecules 2020; 53: 2547
    CrossrefPubMed
    • 59a Guo L, Zou C, Dai S, Chen C. Polymer 2017; 9: 122
      CrossrefPubMed
    • 59b Takeuchi D, Yamada T, Nakamaru Y, Osakada K, Aratani I, Suzuki Y. Organometallics 2019; 38: 2323
      CrossrefPubMed
  • 60 Stehling UM, Stein KM, Fischer D, Waymouth RM. Macromolecules 1999; 32: 14
    CrossrefPubMed
  • 61 Bruzaud S, Cramail H, Duvignac L, Deffieux A. Macromol. Chem. Phys. 1997; 198: 291
    CrossrefPubMed
  • 62 Cui X, Gu G, Li C, Liu N, Gong Y, Liu B. Polymer 2020; 202: 122739
    CrossrefPubMed
  • 63 Na Y, Chen C. Angew. Chem. Int. Ed. 2020; 59: 7953
    CrossrefPubMed
  • 64 Rodrigues AS, Kirillov E, Carpentier JF. Coord. Chem. Rev. 2008; 252: 2115
    CrossrefPubMed
  • 65 Shin J, Jensen SM, Ju J, Lee S, Xue Z, Noh SK, Bae C. Macromolecules 2007; 40: 8600
    CrossrefPubMed
  • 66 Liu D, Wang M, Wang Z, Wu C, Pan Y, Cui D. Angew. Chem. Int. Ed. 2017; 56: 2714
    CrossrefPubMed
  • 67 Wang H, Wu X, Yang Y, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2020; 59: 7173
    CrossrefPubMed
  • 69 Neuwald B, Caporaso L, Cavallo L, Mecking S. J. Am. Chem. Soc. 2013; 135: 1026
    CrossrefPubMed
  • 70 Nakamura A, Kageyama T, Goto H, Carrow BP, Ito S, Nozaki K. J. Am. Chem. Soc. 2012; 134: 12366
    CrossrefPubMed
  • 71 Wang C, Luo G, Nishiura M, Song G, Yamamoto A, Luo Y, Hou Z. Sci. Adv. 2017; 3: e1701011
    CrossrefPubMed
  • 72 Chai Y, Wu C, Liu D, Run M, Cui D. Sci. China Chem. 2019; 62: 761
    CrossrefPubMed
  • 73 Liu Z, Xu T. Polym. Chem. 2022; 13: 2477
    CrossrefPubMed
    • 74a Kim Y, Do Y. Macromol. Rapid Commun. 2000; 21: 1148
      CrossrefPubMed
    • 74b Kim Y, Park S, Han Y, Do Y. Bull. Korean Chem. Soc. 2004; 25: 1648
      CrossrefPubMed
  • 75 Wang Z, Liu D, Cui D. Macromolecules 2016; 49: 781
    CrossrefPubMed
  • 76 van de Wouw HL, Klausen RS. J. Org. Chem. 2019; 84: 1117
    CrossrefPubMed
  • 77 Wang R, Liu D, Li X, Zhang J, Cui D, Wan X. Macromolecules 2016; 49: 2502
    CrossrefPubMed
  • 78 Liu D, Wang M, Chai Y, Wan X, Cui D. ACS Catal. 2019; 9: 2618
    CrossrefPubMed
  • 79 Shi X, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2016; 55: 14812
    CrossrefPubMed
  • 80 Yuki H, Okamoto Y, Kuwae Y, Hatada K. J. Polym. Sci., Part A: Polym. Chem. 1969; 7: 1933
    CrossrefPubMed
    • 81a Liu D, Yao C, Wang R, Wang M, Wang Z, Wu C, Lin F, Li S, Wan X, Cui D. Angew. Chem. Int. Ed. 2015; 54: 5205
      CrossrefPubMed
    • 81b Chai Y, Wang L, Liu D, Wang Z, Run M, Cui D. Chem. Eur. J. 2019; 25: 2043
      CrossrefPubMed
    • 82a Roeder J, Oliveira RVB, Gonçalves MC, Soldi V, Pires ATN. Polym. Test. 2002; 21: 815
      CrossrefPubMed
    • 82b Lin Z, Guan Z, Xu B, Chen C, Guo G, Zhou J, Xian J, Cao L, Wang Y, Li M, Li W. J. Ind. Eng. Chem. 2013; 19: 692
      CrossrefPubMed
  • 83 Faisant JB, Aït-Kadi A, Bousmina M, Deschênes L. Polymer 1998; 39: 533
    CrossrefPubMed
    • 84a Hristov VN, Krumova M, Vasileva S, Michler GH. J. Appl. Polym. Sci. 2004; 92: 1286
      CrossrefPubMed
    • 84b Zhang X, Yang H, Lin Z, Tan S. J. Thermoplast. Compos. Mater. 2013; 26: 16
      CrossrefPubMed
    • 85a Ginzburg A, Ramakrishnan V, Rongo L, Rozanski A, Bouyahyi M, Jasinska-Walc L, Duchateau R. Rheol. Acta 2020; 59: 601
      CrossrefPubMed
    • 85b Jasinska-Walc L, Bouyahyi M, Kruszynski J, Tercjak A, Rozanski A, Troisi EM, Liu Y, Yang L, Ivashkiv O, Sienkiewicz M, Duchateau R. ACS Appl. Polym. Mater. 2021; 3: 5509
      CrossrefPubMed
    • 85c Rozanski A, Jasinska-Walc L, Bouyahyi M, Yang L, Duchateau R, Defize T, Bernaerts K. VWO2020/200688 (SABIC Global Technologies B.V.) 2020
      PubMed
  • 86 Jasinska-Walc L, Bouyahyi M, Duchateau R. Acc. Chem. Res. 2022; 55: 1985
    CrossrefPubMed
  • 87 Chung TCM. Macromolecules 2013; 46: 6671
    CrossrefPubMed
  • 88 Yuan X, Matsuyama Y, Chung TCM. Macromolecules 2010; 43: 4011
    CrossrefPubMed
    • 89a Yuan X, Chung TCM. Appl. Phys. Lett. 2011; 98: 062901
      CrossrefPubMed
    • 89b Martín A, Hoyos M, Gómez-Elvira JM. ACS Appl. Energy Mater. 2021; 4: 25
      CrossrefPubMed
  • 90 Zhang M, Li B, Wang J, Huang H, Zhang L, Chen L. Adv. Mater. 2021; 33: 2008198
    CrossrefPubMed