Recent Progress on COS-derived Polymers
English
Recent Progress on COS-derived Polymers
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Key words:
- Carbonyl sulfide
- / Epoxide
- / Copolymerization
- / Poly(monothiocarbonate)
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[1]
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
-
[2]
Zhu, Y.; Romain, C.; Williams, C. K. Sustainable polymers from renewable resources. Nature 2016, 540, 354. doi: 10.1038/nature21001
-
[3]
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
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
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
-
[8]
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
-
[9]
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
-
[10]
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
-
[11]
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
-
[12]
Qin, A.; Lam, J. W. Y.; Tang, B. Z. Click polymerization: progresses, challenges, and opportunities. Macromolecules 2010, 43, 8693-8702. doi: 10.1021/ma101064u
-
[13]
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
-
[14]
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
-
[15]
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
-
[16]
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
-
[17]
Napoli, A.; Valentini, M.; Tirelli, N.; Müller, M.; Hubbell, J. A. Oxidation-responsive polymeric vesicles. Nat. Mater. 2004, 3, 183. doi: 10.1038/nmat1081
-
[18]
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
-
[19]
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
-
[20]
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
-
[21]
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
-
[22]
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
-
[23]
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
-
[24]
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.
-
[25]
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
-
[26]
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
-
[27]
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
-
[28]
Coates, G. W.; Moore, D. R. Discrete metal-based catalysts for the copolymerization CO2 and epoxides: Discovery, reactivity, optimization, and mechanism. Angew. Chem. Int. Ed. 2004, 43, 6618-6639. doi: 10.1002/(ISSN)1521-3773
-
[29]
Darensbourg, D. J. Making plastics from carbon dioxide: Salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO2. Chem. Rev. 2007, 107, 2388-2410. doi: 10.1021/cr068363q
-
[30]
Lu, X. B.; Ren, W. M.; Wu, G. P. CO2 copolymers from epoxides: Catalyst activity, product selectivity, and stereochemistry control. Acc. Chem. Res. 2012, 45, 1721-1735. doi: 10.1021/ar300035z
-
[31]
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
-
[32]
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
-
[33]
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
-
[34]
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
-
[35]
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
-
[36]
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
-
[37]
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
-
[38]
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
-
[39]
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
-
[40]
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
-
[41]
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
-
[42]
Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. 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+
-
[43]
MacMillan, D. W. C. The advent and development of organocatalysis. Nature 2008, 455, 304. doi: 10.1038/nature07367
-
[44]
Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Organocatalysis: Opportunities and challenges for polymer synthesis Macromolecules 2010, 43, 2093-2107.
-
[45]
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
-
[46]
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
-
[47]
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
-
[48]
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
-
[49]
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
-
[50]
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
-
[51]
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
-
[52]
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
-
[53]
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
-
[54]
Takahashi, Y.; Kojima, R. Crystal structure of poly(trimethylene carbonate). Macromolecules 2003, 36, 5139-5143. doi: 10.1021/ma030076q
-
[55]
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
-
[56]
Bates, C. M.; Bates, F. S. 50th anniversary perspective: Block polymers—pure potential. Macromolecules 2017, 50, 3-22. doi: 10.1021/acs.macromol.6b02355
-
[57]
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
-
[58]
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
-
[59]
Wang, Z.; Yuan, L.; Tang, C. Sustainable elastomers from renewable biomass. Acc. Chem. Res. 2017, 50, 1762-1773. doi: 10.1021/acs.accounts.7b00209
-
[60]
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
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