Recent Progress on COS-derived Polymers

Cheng-Jian Zhang; Xing-Hong Zhang

doi:10.1007/s10118-019-2288-y

Your Location：

Home >

Browse articles >

Recent Progress on COS-derived Polymers

REVIEW | Updated：2021-02-18

- Recent Progress on COS-derived Polymers
- Chinese Journal of Polymer Science Vol. 37, Issue 10, Pages: 951-958(2019)
- Affiliations：
  
  Key Laboratory of Macromolecular Synthesis and Functionalization (Ministry of Education), Department of Polymer Science & Engineering, Zhejiang University, Hangzhou 310027, China
- Author bio：
  
  xhzhang@zju.edu.cn
- Funds：
- DOI：10.1007/s10118-019-2288-y
  CLC：
- Received：28 March 2019，
  
  Revised：2019-4-23，
  
  Accepted：29 April 2019，
  
  Online First：01 July 2019，
  
  Published：2019-10
- Accepted：
Scan QR Code
Zhang, C. J.; Zhang, X. H. Recent progress on COS-derived polymers. Chinese J. Polym. Sci. 2019, 37, 951–958.

Cheng-Jian Zhang, Xing-Hong Zhang. Recent Progress on COS-derived Polymers[J]. Chinese Journal of Polymer Science, 2019, 37(10): 951-958.
Zhang, C. J.; Zhang, X. H. Recent progress on COS-derived polymers. Chinese J. Polym. Sci. 2019, 37, 951–958. DOI： 10.1007/s10118-019-2288-y.

Cheng-Jian Zhang, Xing-Hong Zhang. Recent Progress on COS-derived Polymers[J]. Chinese Journal of Polymer Science, 2019, 37(10): 951-958. DOI： 10.1007/s10118-019-2288-y.

摘要

Abstract

The synthesis of sulfur-containing polymer

a very promising functional material

has made a great progress in the past several years. This review is focused on the very recent advances in poly(monothiocarbonate)s derived from carbonyl sulfide (COS) and epoxides including biomass-derived epoxides. Of significance

metal-free catalyst systems

including triethyl borane/Lewis base pair and thiourea/Lewis base pair are developed for the alternating copolymerization of COS with epoxides. Thereof

the thiourea/Lewis base pair is highly active to the copolymerization of COS with epoxide in a living manner. Moreover

a series of crystalline poly(monothiocarbonate)s are presented

including the copolymers derived from COS with oxetane

ethylene oxide

enantiopure epichlorohydrin

and achiral

meso

-epoxides

via

enantioselective copolymerization. Based on these COS/epoxide copolymerization process

a variety of COS-based block copolymers with well-defined structure are presented.

关键词

Keywords

references

Zhang, X.; Fevre, M.; Jones, G. O.; Waymouth, R. M . Catalysis as an enabling science for sustainable polymers . Chem. Rev. , 2018 . 118 839 - 885 . DOI: 10.1021/acs.chemrev.7b00329 http://doi.org/10.1021/acs.chemrev.7b00329 .

Zhu, Y.; Romain, C.; Williams, C. K . Sustainable polymers from renewable resources . Nature , 2016 . 540 354 DOI: 10.1038/nature21001 http://doi.org/10.1038/nature21001 .

Raffa, P.; Wever, D. A. Z.; Picchioni, F.; Broekhuis, A. A . Polymeric surfactants: Synthesis, properties, and links to applications . Chem. Rev. , 2015 . 115 8504 - 8563 . DOI: 10.1021/cr500129h http://doi.org/10.1021/cr500129h .

Zhu, J. B.; Watson, E. M.; Tang, J.; Chen, E. Y. X . A synthetic polymer system with repeatable chemical recyclability . Science , 2018 . 360 398 - 403 . DOI: 10.1126/science.aar5498 http://doi.org/10.1126/science.aar5498 .

Hong, M.; Chen, J.; Chen, E. Y. X . Polymerization of polar monomers mediated by main-group Lewis acid–base pairs . Chem. Rev. , 2018 . 118 10551 - 10616 . DOI: 10.1021/acs.chemrev.8b00352 http://doi.org/10.1021/acs.chemrev.8b00352 .

Mutlu, H.; Ceper, E. B.; Li, X.; Yang, J.; Dong, W.; Ozmen, M. M.; Theato, P . Sulfur chemistry in polymer and materials science . Macromol. Rapid Commun. , 2019 . 40 1800650 DOI: 10.1002/marc.201800650 http://doi.org/10.1002/marc.201800650 .

Sarapas, J. M.; Tew, G. N . Thiol-ene step-growth as a versatile route to functional polymers . Angew. Chem. Int. Ed. , 2016 . 55 15860 - 15863 . DOI: 10.1002/anie.201609023 http://doi.org/10.1002/anie.201609023 .

Ochiai, B.; Endo, T . Carbon dioxide and carbon disulfide as resources for functional polymers . Prog. Polym. Sci. , 2005 . 30 183 - 215 . DOI: 10.1016/j.progpolymsci.2005.01.005 http://doi.org/10.1016/j.progpolymsci.2005.01.005 .

Luo, M.; Li, Y.; Zhang, Y. Y.; Zhang, X. H . Using carbon dioxide and its sulfur analogues as monomers in polymer synthesis . Polymer , 2016 . 82 406 - 431 . DOI: 10.1016/j.polymer.2015.11.011 http://doi.org/10.1016/j.polymer.2015.11.011 .

He, L.; Zhao, H.; Theato, P . No heat, no light—The future of sulfur polymers prepared at room temperature is bright . Angew. Chem. Int. Ed. , 2018 . 57 13012 - 13014 . DOI: 10.1002/anie.201807005 http://doi.org/10.1002/anie.201807005 .

Yuan, J.; Xiong, W.; Zhou, X.; Zhang, Y.; Shi, D.; Li, Z.; Lu, H . 4-Hydroxyproline-derived sustainable polythioesters: Controlled ring-opening polymerization, complete recyclability, and facile functionalization . J. Am. Chem. Soc. , 2019 . 141 4928 - 4935 . DOI: 10.1021/jacs.9b00031 http://doi.org/10.1021/jacs.9b00031 .

Qin, A.; Lam, J. W. Y.; Tang, B. Z . Click polymerization: Progresses, challenges, and opportunities . Macromolecules , 2010 . 43 8693 - 8702 . DOI: 10.1021/ma101064u http://doi.org/10.1021/ma101064u .

Diebler, J.; Komber, H.; Häußler, L.; Lederer, A.; Werner, T . Alkoxide-initiated regioselective coupling of carbon disulfide and terminal epoxides for the synthesis of strongly alternating copolymers . Macromolecules , 2016 . 49 4723 - 4731 . DOI: 10.1021/acs.macromol.6b00728 http://doi.org/10.1021/acs.macromol.6b00728 .

Nakano, K.; Tatsumi, G.; Nozaki, K . Synthesis of sulfur-rich polymers: Copolymerization of episulfide with carbon disulfide by using [PPN]Cl/(salph)Cr(III)Cl system . J. Am. Chem. Soc. , 2007 . 129 15116 DOI: 10.1021/ja076056b http://doi.org/10.1021/ja076056b .

Chung, W. J.; Simmonds, A. G.; Griebel, J. J.; Kim, E. T.; Suh, H. S.; Shim, I. B.; Glass, R. S.; Loy, D. A.; Theato, P.; Sung, Y. E.; Char, K.; Pyun, J . Elemental sulfur as a reactive medium for gold nanoparticles and nanocomposite materials . Angew. Chem. Int. Ed. , 2011 . 50 11409 - 11412 . DOI: 10.1002/anie.v50.48 http://doi.org/10.1002/anie.v50.48 .

Bearinger, J. P.; Terrettaz, S.; Michel, R.; Tirelli, N.; Vogel, H.; Textor, M.; Hubbell, J. A . Chemisorbed poly(propylene sulphide)-based copolymers resist biomolecular interactions . Nat. Mater. , 2003 . 2 259 DOI: 10.1038/nmat851 http://doi.org/10.1038/nmat851 .

Napoli, A.; Valentini, M.; Tirelli, N.; Müller, M.; Hubbell, J. A . Oxidation-responsive polymeric vesicles . Nat. Mater. , 2004 . 3 183 DOI: 10.1038/nmat1081 http://doi.org/10.1038/nmat1081 .

Lim, J.; Pyun, J.; Char, K . Recent approaches for the direct use of elemental sulfur in the synthesis and processing of advanced materials . Angew. Chem. Int. Ed. , 2015 . 54 3249 - 3258 . DOI: 10.1002/anie.201409468 http://doi.org/10.1002/anie.201409468 .

Je, S. H.; Buyukcakir, O.; Kim, D.; Coskun, A . Direct utilization of elemental sulfur in the synthesis of microporous polymers for natural gas sweetening . Chem , 2016 . 1 482 - 493 . DOI: 10.1016/j.chempr.2016.08.003 http://doi.org/10.1016/j.chempr.2016.08.003 .

Griebel, J. J.; Glass, R. S.; Char, K.; Pyun, J . Polymerizations with elemental sulfur: A novel route to high sulfur content polymers for sustainability, energy and defense . Prog. Polym. Sci. , 2016 . 58 90 - 125 . DOI: 10.1016/j.progpolymsci.2016.04.003 http://doi.org/10.1016/j.progpolymsci.2016.04.003 .

Chung, W. J.; Griebel, J. J.; Kim, E. T.; Yoon, H.; Simmonds, A. G.; Ji, H. J.; Dirlam, P. T.; Glass, R. S.; Wie, J. J.; Nguyen, N. A.; Guralnick, B. W.; Park, J.; Somogyi, Á.; Theato, P.; Mackay, M. E.; Sung, Y. E.; Char, K.; Pyun, J . The use of elemental sulfur as an alternative feedstock for polymeric materials . Nat. Chem. , 2013 . 5 518 DOI: 10.1038/nchem.1624 http://doi.org/10.1038/nchem.1624 .

Sun, Z.; Huang, H.; Li, L.; Liu, L.; Chen, Y . Polythioamides of high refractive index by direct polymerization of aliphatic primary diamines in the presence of elemental sulfur . Macromolecules , 2017 . 50 8505 - 8511 . DOI: 10.1021/acs.macromol.7b01788 http://doi.org/10.1021/acs.macromol.7b01788 .

Tian, T.; Hu, R.; Tang, B. Z . Room temperature one-step conversion from elemental sulfur to functional polythioureas through catalyst-free multicomponent polymerizations . J. Am. Chem. Soc. , 2018 . 140 6156 - 6163 . DOI: 10.1021/jacs.8b02886 http://doi.org/10.1021/jacs.8b02886 .

Li, W.; Wu, X.; Zhao, Z.; Qin, A.; Hu, R.; Tang, B. Z . Catalyst-free, atom-economic, multicomponent polymerizations of aromatic diynes, elemental sulfur, and aliphatic diamines toward luminescent polythioamides . Macromolecules , 2015 . 48 ( 7747 ): 7754 .

Luo, M.; Zhang, X. H.; Darensbourg, D. J . Poly(monothiocarbonate)s from the alternating and regioselective copolymerization of carbonyl sulfide with epoxides . Acc. Chem. Res. , 2016 . 49 2209 - 2219 . DOI: 10.1021/acs.accounts.6b00345 http://doi.org/10.1021/acs.accounts.6b00345 .

Rasmussen, R. A.; Khalil, M. A. K.; Dalluge, R. W.; Penkett, S. A.; Jones, B . Carbonyl sulfide and carbondisulfide from the eruptions of Mount St. Helens . Science , 1982 . 215 665 - 667 . DOI: 10.1126/science.215.4533.665 http://doi.org/10.1126/science.215.4533.665 .

Farrell, W. S.; Zavalij, P. Y.; Sita, L. R . Metal-catalyzed " on-demand” production of carbonyl sulfide from carbon monoxide and elemental sulfur . Angew. Chem. Int. Ed. , 2015 . 54 4269 - 4273 . DOI: 10.1002/anie.201410353 http://doi.org/10.1002/anie.201410353 .

Coates, G. W.; Moore, D. R . Discrete metal-based catalysts for the copolymerization CO 2 and epoxides: Discovery, reactivity, optimization, and mechanism . Angew. Chem. Int. Ed. , 2004 . 43 6618 - 6639 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

Darensbourg, D. J . Making plastics from carbon dioxide: Salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO 2 . Chem. Rev. , 2007 . 107 2388 - 2410 . DOI: 10.1021/cr068363q http://doi.org/10.1021/cr068363q .

Lu, X. B.; Ren, W. M.; Wu, G. P . CO 2 copolymers from epoxides: Catalyst activity, product selectivity, and stereochemistry control . Acc. Chem. Res. , 2012 . 45 1721 - 1735 . DOI: 10.1021/ar300035z http://doi.org/10.1021/ar300035z .

Luo, M.; Zhang, X. H.; Du, B. Y.; Wang, Q.; Fan, Z. Q . Regioselective and alternating copolymerization of carbonyl sulfide with racemic propylene oxide . Macromolecules , 2013 . 46 5899 - 5904 . DOI: 10.1021/ma401114m http://doi.org/10.1021/ma401114m .

Ren, W. M.; Liu, Y.; Xin, A. X.; Fu, S.; Lu, X. B . Single-site bifunctional catalysts for COX (X = O or S)/epoxides copolymerization: Combining high activity, selectivity, and durability . Macromolecules , 2015 . 48 8445 - 8450 . DOI: 10.1021/acs.macromol.5b02108 http://doi.org/10.1021/acs.macromol.5b02108 .

Gu, G. G.; Yue, T. J.; Wan, Z. Q.; Zhang, R.; Lu, X. B.; Ren, W. M . A single-site iron(III)-salan catalyst for converting COS to sulfur-containing polymers . Polymers , 2017 . 9 515 DOI: 10.3390/polym9100515 http://doi.org/10.3390/polym9100515 .

Luo, M.; Zhang, X. H.; Darensbourg, D. J . Highly regioselective and alternating copolymerization of carbonyl sulfide with phenyl glycidyl ether . Polym. Chem. , 2015 . 6 6955 - 6958 . DOI: 10.1039/C5PY01197C http://doi.org/10.1039/C5PY01197C .

Luo, M.; Zhang, X. H.; Darensbourg, D. J . An investigation of the pathways for oxygen/sulfur scramblings during the copolymerization of carbon disulfide and oxetane . Macromolecules , 2015 . 48 5526 - 5532 . DOI: 10.1021/acs.macromol.5b01251 http://doi.org/10.1021/acs.macromol.5b01251 .

Luo, M.; Zhang, X. H.; Du, B. Y.; Wang, Q.; Fan, Z. Q . Well-defined high refractive index poly(monothiocarbonate) with tunable Abbe's numbers and glass-transition temperatures via terpolymerization . Polym. Chem. , 2015 . 6 4978 - 4983 . DOI: 10.1039/C5PY00773A http://doi.org/10.1039/C5PY00773A .

Luo, M.; Zhang, X. H.; Darensbourg, D. J . An examination of the steric and electronic effects in the copolymerization of carbonyl sulfide and styrene oxide . Macromolecules , 2015 . 48 6057 - 6062 . DOI: 10.1021/acs.macromol.5b01427 http://doi.org/10.1021/acs.macromol.5b01427 .

Luo, M.; Zhang, X. H.; Du, B. Y.; Wang, Q.; Fan, Z. Q . Alternating copolymerization of carbonyl sulfide and cyclohexene oxide catalyzed by zinc-cobalt double metal cyanide complex . Polymer , 2014 . 55 3688 - 3695 . DOI: 10.1016/j.polymer.2014.05.065 http://doi.org/10.1016/j.polymer.2014.05.065 .

Zhang, C. J.; Yang, J. L.; Hu, L F.; Zhang, X. H . Anionic copolymerization of carbonyl sulfide with epoxides via alkali metal alkoxides . Chin. J. Chem. , 2018 . 36 625 - 626 . DOI: 10.1002/cjoc.v36.7 http://doi.org/10.1002/cjoc.v36.7 .

Hu, S.; Zhao, J.; Zhang, G.; Schlaad, H . Macromolecular architectures through organocatalysis . Prog. Polym. Sci. , 2017 . 74 34 - 77 . DOI: 10.1016/j.progpolymsci.2017.07.002 http://doi.org/10.1016/j.progpolymsci.2017.07.002 .

Ottou, W. N.; Sardon, H.; Mecerreyes, D.; Vignolle, J.; Taton, D . Update and challenges in organo-mediated polymerization reactions . Prog. Polym. Sci. , 2016 . 56 64 - 115 . DOI: 10.1016/j.progpolymsci.2015.12.001 http://doi.org/10.1016/j.progpolymsci.2015.12.001 .

Pratt, R . Triazabicyclodecene: A simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters . J. Am. Chem. Soc. , 2006 . 128 4556 - 4557 . DOI: 10.1021/ja060662+ http://doi.org/10.1021/ja060662+ .

MacMillan, D. W. C . The advent and development of organocatalysis . Nature , 2008 . 455 304 DOI: 10.1038/nature07367 http://doi.org/10.1038/nature07367 .

Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M . Organocatalysis: Opportunities and challenges for polymer synthesis . Macromolecules , 2014 . 43 2093 - 2107 . .

Zhang, C. J.; Hu, L. F.; Wu, H. L.; Cao, X. H.; Zhang, X. H . Dual organocatalysts for highly active and selective synthesis of linear poly( γ -butyrolactone)s with high molecular weights . Macromolecules , 2018 . 51 8705 - 8711 . DOI: 10.1021/acs.macromol.8b01757 http://doi.org/10.1021/acs.macromol.8b01757 .

Zhang, C.; Duan, H.; Hu, L.; Zhang, C.; Zhang, X . Metal-free route to precise synthesis of poly(propylene oxide) and its blocks with high activity . ChemSusChem , 2018 . 11 4209 - 4213 . DOI: 10.1002/cssc.v11.24 http://doi.org/10.1002/cssc.v11.24 .

Yang, J. L.; Wu, H. L.; Li, Y.; Zhang, X. H.; Darensbourg, D. J . Perfectly alternating and regioselective copolymerization of carbonyl sulfide and epoxides by metal-free Lewis pairs . Angew. Chem. Int. Ed. , 2017 . 56 5774 - 5779 . DOI: 10.1002/anie.201701780 http://doi.org/10.1002/anie.201701780 .

Zhang, C. J.; Wu, H. L.; Li, Y.; Yang, J. L.; Zhang, X. H . Precise synthesis of sulfur-containing polymers via cooperative dual organocatalysts with high activity . Nat. Commun. , 2018 . 9 2137 DOI: 10.1038/s41467-018-04554-5 http://doi.org/10.1038/s41467-018-04554-5 .

Yue, T. J.; Ren, W. M.; Liu, Y.; Wan, Z. Q.; Lu, X. B . Crystalline polythiocarbonate from stereoregular copolymerization of carbonyl sulfide and epichlorohydrin . Macromolecules , 2016 . 49 2971 - 2976 . DOI: 10.1021/acs.macromol.6b00272 http://doi.org/10.1021/acs.macromol.6b00272 .

Wu, H. L.; Yang, J. L.; Luo, M.; Wang, R. Y.; Xu, J. T.; Du, B. Y.; Zhang, X. H.; Darensbourg, D. J . Poly(trimethylene monothiocarbonate) from the alternating copolymerization of COS and oxetane: A semicrystalline copolymer . Macromolecules , 2016 . 49 8863 - 8868 . DOI: 10.1021/acs.macromol.6b02285 http://doi.org/10.1021/acs.macromol.6b02285 .

Zhang, X. H.; Liu, F.; Sun, X. K.; Chen, S.; Du, B. Y.; Qi, G. R.; Wan, K. M . Atom-exchange coordination polymerization of carbon disulfide and propylene oxide by a highly effective double-metal cyanide complex . Macromolecules , 2008 . 41 1587 - 1590 . DOI: 10.1021/ma702290g http://doi.org/10.1021/ma702290g .

Ren, W. M.; Yue, T. J.; Li, M. R.; Wan, Z. Q.; Lu, X. B . Crystalline and elastomeric poly(monothiocarbonate)s prepared from copolymerization of COS and achiral epoxide . Macromolecules , 2017 . 50 63 - 68 . DOI: 10.1021/acs.macromol.6b02089 http://doi.org/10.1021/acs.macromol.6b02089 .

Cao, X. H.; Yang, J. L.; Wu, H. L.; Wang, R. Y.; Zhang, X. H.; Xu, J. T . Crystallization behavior and morphology of novel aliphatic poly(monothiocarbonate)s . Polymer , 2019 . 165 112 - 123 . DOI: 10.1016/j.polymer.2019.01.030 http://doi.org/10.1016/j.polymer.2019.01.030 .

Takahashi, Y.; Kojima, R . Crystal structure of poly(trimethylene carbonate) . Macromolecules , 2003 . 36 5139 - 5143 . DOI: 10.1021/ma030076q http://doi.org/10.1021/ma030076q .

Yue, T. J.; Ren, W. M.; Chen, L.; Gu, G. G.; Liu, Y.; Lu, X. B . Synthesis of chiral sulfur-containing polymers: Asymmetric copolymerization of meso-epoxides and carbonyl sulfide . Angew. Chem. Int. Ed. , 2018 . 130 12852 - 12856 . DOI: 10.1002/ange.201805200 http://doi.org/10.1002/ange.201805200 .

Bates, C. M.; Bates, F. S . 50 th Anniversary perspective: Block polymers—Pure potential . Macromolecules , 2017 . 50 3 - 22 . DOI: 10.1021/acs.macromol.6b02355 http://doi.org/10.1021/acs.macromol.6b02355 .

Li, Y.; Duan, H. Y.; Luo, M.; Zhang, Y. Y.; Zhang, X. H.; Darensbourg, D. J . Mechanistic study of regio-defects in the copolymerization of propylene oxide/carbonyl sulfide catalyzed by (salen)CrX Complexes . Macromolecules , 2017 . 50 8426 - 8437 . DOI: 10.1021/acs.macromol.7b01867 http://doi.org/10.1021/acs.macromol.7b01867 .

Yang, J. L.; Cao, X. H.; Zhang, C. J.; Wu, H. L.; Zhang, X. H . Highly efficient one-pot synthesis of COS-based block copolymers by using organic Lewis pairs . Molecules , 2018 . 23 298 DOI: 10.3390/molecules23020298 http://doi.org/10.3390/molecules23020298 .

Wang, Z.; Yuan, L.; Tang, C . Sustainable elastomers from renewable biomass . Acc. Chem. Res. , 2017 . 50 1762 - 1773 . DOI: 10.1021/acs.accounts.7b00209 http://doi.org/10.1021/acs.accounts.7b00209 .

Hu, L. F.; Li, Y.; Liu, B.; Zhang, Y. Y.; Zhang, X. H . Alternating and regioregular copolymers with high refractive index from COS and biomass-derived epoxides . RSC Adv. , 2017 . 7 49490 - 49497 . DOI: 10.1039/C7RA08958A http://doi.org/10.1039/C7RA08958A .

Views

117

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Flexible Gradient Poly(ether-ester) from the Copolymerization of Epoxides and ε-Caprolactone Mediated by a Hetero-bimetallic Complex

Mechanism-inspired Design of Heterodinuclear Catalysts for Copolymerization of Epoxide and Lactone

Monomer-activated Copolymerization of Ethylene Oxide and Epichlorohydrin: In Situ Kinetics Evidences Tapered Block Copolymer Formation

Chemoselective Ring-opening Copolymerization of CO2-based Lactones towards Functional Polyesters

Super-high Active, Homogeneous Vanadium(V) Complexes Bearing Bidentate Phenoxy-Phosphine Ligands for Diverse Olefins (Co)polymerization

Related Author

Wei-Min Ren

Hong-Juan Gao

Tian-Jun Yue

Rui-Jing Wang

Bai-Hao Ren

Ge-Ge Gu

Ann-Kathrin Danner

Daniel Leibig

Related Institution

State Key Laboratory of Fine Chemicals, Dalian University of Technology

Graduate School Materials Science in Mainz, Staudinger Weg 9

Institute of Organic Chemistry, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14

Key Laboratory of Medical Electronics and Digital Health of Zhejiang Province, Jiaxing University

MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University

⁰