

FOLLOWUS
a.State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026, China
shihui-li@ciac.ac.cn (S.H.L.)
dmcui@ciac.ac.cn (D.M.C.)
Received:08 July 2020,
Revised:2020-8-6,
Accepted:21 August 2020,
Online First:16 October 2020,
Published:02 January 2021
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Huang, J. M.; Yao, C. G.; Li, S. H.; Cui, D. M. Yttrium-catalyzed , cis,-1,4-selective polymerization of 2-(4-halophenyl)-1,3-butadienes and their copolymerization with isoprene. Chinese J. Polym. Sci. 2021, 39, 309–315
Jian-Ming Huang, Chang-Guang Yao, Shi-Hui Li, et al. Yttrium-catalyzed
Huang, J. M.; Yao, C. G.; Li, S. H.; Cui, D. M. Yttrium-catalyzed , cis,-1,4-selective polymerization of 2-(4-halophenyl)-1,3-butadienes and their copolymerization with isoprene. Chinese J. Polym. Sci. 2021, 39, 309–315 DOI: 10.1007/s10118-021-2505-3.
Jian-Ming Huang, Chang-Guang Yao, Shi-Hui Li, et al. Yttrium-catalyzed
Polymerization of 2-(4-halophenyl)-1
3-butadiene (2-XPB) and their copolymerization with isoprene using a yttrium catalyst have been examined. The
β
-diketiminato yttrium bis(alkyl) complex (
1
) activated by [Ph
3
C][B(C
6
F
5
)
4
] and Al
i
Bu
3
shows high
cis
-1
4-selectivity (
>
98%) for the polymerization of 2-XPB (2-XPB = 2-FPB
2-ClPB and 2-BrPB) to afford halogenated plastic poly(dienes) with glass transition temperatures of 30–55 °C. Moreover
the copolymerization of 2-XPB with isoprene (IP) has also been achieved by this catalyst
and the insertion ratios of 2-XPB can be facilely tuned in a full range of 0%–100% simply by changing the 2-XPB-to-IP ratio. Quantitative hydrogenation of
cis
-1
4-poly(2-XPB) results in perfect alternating ethylene-halostyrene copolymers
and an alternating copolymer of 4-vinylbenzoic acid with ethylene is obtained by a consecutive reaction of ethylene-4-bromostyrene copolymer with
n
BuLi
CO
2
and HCl.
Chen, M.; Chen, C. . Polar and functionalized polyolefins: new catalysts, new modulation strategies and new materials . Acta Polymerica Sinica (in Chinese) , 2018 . 1372 - 1384 . .
Cui, D. . Studies on homo- and co-polymerizations of polar and non-polar monomers using rare-earth metal catalysts . Acta Polymerica Sinica (in Chinese) , 2020 . 51 12 - 29 . .
Dong, J. Y.; Hu, Y. . Design and synthesis of structurally well-defined functional polyolefins via transition metal-mediated olefin polymerization chemistry . Coord. Chem. Rev. , 2006 . 250 47 - 65 . DOI: 10.1016/j.ccr.2005.05.008 http://doi.org/10.1016/j.ccr.2005.05.008 .
Takenaka, K.; Hattori, T.; Hirao, A.; Nakahama, S. . Polymerization of monomers containing functional silyl groups. 6. Anionic polymerization of 2-(trialkoxysilyl)-1,3-butadiene . Macromolecules , 1989 . 22 1563 - 1567 . DOI: 10.1021/ma00194a010 http://doi.org/10.1021/ma00194a010 .
Jing, Y.; Sheares, V. V. . Polar, functionalized diene-based materials. 1. Bulk, solution, and emulsion free radical polymerization of 2-cyanomethyl-1,3-butadiene . Macromolecules , 2000 . 33 6255 - 6261 . DOI: 10.1021/ma9918046 http://doi.org/10.1021/ma9918046 .
Beery, M. D.; Rath, M. K.; Sheares, V. V. . Polar, functionalized diene-based materials. 4. Polymerization studies of 2,3-bis(4-ethoxy-4-oxobutyl)-1,3-butadiene and copolymerization with styrene . Macromolecules , 2001 . 34 2469 - 2475 . DOI: 10.1021/ma001491a http://doi.org/10.1021/ma001491a .
Friebe, L.; Nuyken, O.; Obrecht, W. Neodymium-based Ziegler/Natta catalysts and their application in diene polymerization. In Neodymium based Ziegler catalysts− fundamental chemistry ; Nuyken, O., Ed. Springer, Berlin, Germany, 2006 , pp. 1−154.
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. . Ortho -phosphinobenzenesulfonate: a superb ligand for palladium-catalyzed coordination-insertion copolymerization of polar vinyl monomers . Acc. Chem. Res. , 2013 . 46 1438 - 1449 . DOI: 10.1021/ar300256h http://doi.org/10.1021/ar300256h .
Li, L.; Li, S.; Cui, D. . Highly cis -1,4-selective living polymerization of 3-methylenehepta-1,6-diene and its subsequent thiol-ene reaction: an efficient approach to functionalized diene-based elastomer . Macromolecules , 2016 . 49 1242 - 1251 . DOI: 10.1021/acs.macromol.5b02654 http://doi.org/10.1021/acs.macromol.5b02654 .
Li, L.; Li, S.; Cui, D. . Chemo- and stereoselective polymerization of 3-methylenehepta-1,6-diene and its thiol-ene modification . J. Polym. Sci., Part A: Polym. Chem. , 2017 . 55 1031 - 1039 . DOI: 10.1002/pola.28463 http://doi.org/10.1002/pola.28463 .
Leicht, H.; Huber, S.; Gottker-Schnetmann, I.; Mecking, S. . Allylboration as a versatile tool for the in situ post-polymerization functionalization of 1,4- cis -poly(butadiene) . Polym. Chem. , 2016 . 7 7195 - 7198 . DOI: 10.1039/C6PY01388K http://doi.org/10.1039/C6PY01388K .
Yao, C.; Liu, N.; Long, S.; Wu, C.; Cui, D. . Highly cis -1,4-selective coordination polymerization of polar 2-(4-methoxyphenyl)-1,3-butadiene and copolymerization with isoprene using a beta -diketiminato yttrium bis(alkyl) complex . Polym. Chem. , 2016 . 7 1264 - 1270 . DOI: 10.1039/C5PY01801C http://doi.org/10.1039/C5PY01801C .
Long, S.; Lin, F.; Yao, C.; Cui, D. . Highly cis -1,4 selective living polymerization of unmasked polar 2-(2-methylidenebut-3-enyl)furan and Diels-Alder addition . Macromol. Rapid Commun. , 2017 . 38 1700227 DOI: 10.1002/marc.201700227 http://doi.org/10.1002/marc.201700227 .
Cai, L.; Long, S.; Wu, C.; Li, S.; Yao, C.; Hua, X.; Na, H.; Liu, D.; Tang, T.; Cui, D. . Highly selective cis -1,4 copolymerization of dienes with polar 2-(3-methylidenepent-4-en-1-yl) pyridine: an approach for recyclable elastomers . Polym. Chem. , 2020 . 11 1646 - 1652 . DOI: 10.1039/C9PY01811E http://doi.org/10.1039/C9PY01811E .
Leicht, H.; Goettker-Schnetmann, I.; Mecking, S. . Stereoselective copolymerization of butadiene and functionalized 1,3-dienes . ACS Macro Lett. , 2016 . 5 777 - 780 . DOI: 10.1021/acsmacrolett.6b00321 http://doi.org/10.1021/acsmacrolett.6b00321 .
Leicht, H.; Goettker-Schnetmann, I.; Mecking, S. . Stereoselective copolymerization of butadiene and functionalized 1,3-dienes with neodymium-based catalysts . Macromolecules , 2017 . 50 8464 - 8468 . DOI: 10.1021/acs.macromol.7b02007 http://doi.org/10.1021/acs.macromol.7b02007 .
Tang, M.; Zhang, R.; Li, S.; Zeng, J.; Luo, M.; Xu, Y. X.; Huang, G. . Towards a supertough thermoplastic polyisoprene elastomer based on a biomimic strategy . Angew. Chem. Int. Ed. , 2018 . 57 15836 - 15840 . DOI: 10.1002/anie.201809339 http://doi.org/10.1002/anie.201809339 .
Gan, Q.; Xu, Y.; Huang, W.; Luo, W.; Hu, Z.; Tang, F.; Jia, X.; Gong, D. . Utilization of bio-sourced myrcene for efficient preparation of highly cis -1,4 regular elastomer via a neodymium catalyzed copolymerization strategy . Polym. Int. , 2020 . 69 763 - 770 . DOI: 10.1002/pi.6011 http://doi.org/10.1002/pi.6011 .
Kharitonov, A. P.; Taege, R.; Ferrier, G.; Teplyakov, V. V.; Syrtsova, D. A.; Koops, G. H. . Direct fluorination-useful tool to enhance commercial properties of polymer articles . J. Fluorine Chem. , 2005 . 126 251 - 263 . DOI: 10.1016/j.jfluchem.2005.01.016 http://doi.org/10.1016/j.jfluchem.2005.01.016 .
Altarawneh, M.; Saeed, A.; Al-Harahsheh, M.; Dlugogorski, B. Z. . Thermal decomposition of brominated flame retardants (BFRs): products and mechanisms . Prog. Energ. Combust. , 2019 . 70 212 - 259 . DOI: 10.1016/j.pecs.2018.10.004 http://doi.org/10.1016/j.pecs.2018.10.004 .
Guo, F.; Jiao, N.; Jiang, L.; Li, Y.; Hou, Z. . Scandium-catalyzed syndiospecific polymerization of halide-substituted styrenes and their copolymerization with styrene . Macromolecules , 2017 . 50 8398 - 8405 . DOI: 10.1021/acs.macromol.7b01668 http://doi.org/10.1021/acs.macromol.7b01668 .
Wang, Z.; Wang, M.; Liu, J.; Liu, D.; Cui, D. . Rapid syndiospecific (co)polymerization of fluorostyrene with high monomer conversion . Chem. Eur. J. , 2017 . 23 18151 - 18155 . DOI: 10.1002/chem.201704584 http://doi.org/10.1002/chem.201704584 .
Wang, T.; Liu, D.; Cui, D. . Highly syndioselective coordination (co)polymerization of ortho -fluorostyrene . Macromolecules , 2019 . 52 ( 24 ): 9555 - 9560 . DOI: 10.1021/acs.macromol.9b01981 http://doi.org/10.1021/acs.macromol.9b01981 .
Li, D.; Li, S.; Cui, D.; Zhang, X. β -Diketiminato rare-earth metal complexes. structures, catalysis, and active species for highly cis-1,4-selective polymerization of isoprene. Organometallics 2010 , 29, 2186−2193.
Wang, L.; Cui, D.; Hou, Z.; Li, W.; Li, Y. . Highly cis -1,4-selective living polymerization of 1,3-conjugated dienes and copolymerization with ε-caprolactone by bis(phosphino)carbazolide rare-earth-metal complexes . Organometallics , 2011 . 30 757 - 767 . .
Li, S.; Liu, D.; Wang, Z.; Cui, D. . Development of group 3 catalysts for alternating copolymerization of ethylene and styrene derivatives . ACS Catal. , 2018 . 8 6086 - 6093 . DOI: 10.1021/acscatal.8b00885 http://doi.org/10.1021/acscatal.8b00885 .
Xu, G. . Copolymerization of ethylene with styrene catalyzed by the [ η 1 : η 5 - tert -butyl(dimethylfluorenylsilyl)amido]methyltitanium “cation” . Macromolecules , 1998 . 31 2395 - 2402 . DOI: 10.1021/ma971480q http://doi.org/10.1021/ma971480q .
Li, W.; Li, Y.; Hu, Y.; Wang, L.; Cui, D.; Wang, Y. . Synthesis and characterization of well-defined alternating ethylene-propylene copolymer . Acta Polymerica Sinica (in Chinese) , 2010 . 961 - 965 . .
Suzuki, T.; Tsuji, Y.; Watanabe, Y.; Takegami, Y. . High-resolution NMR spectra of hydrogenated poly(phenylbutadienes) . Macromolecules , 1980 . 13 849 - 852 . .
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