Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization

Jin-Ying Wang; Yuan-Yuan Ni; Jian-Nan Cheng; Li-Fen Zhang; Zhen-Ping Cheng

doi:10.1007/s10118-021-2602-3

Your Location：

Home >

Browse articles >

Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization

ARTICLE | Updated：2021-07-20

- Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization
- Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization
- Chinese Journal of Polymer Science 2021年39卷第9期页码：1155-1160
- Affiliations：
  
  State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
- Author bio：
  
  zhanglifen@suda.edu.cn (L.F.Z.)
  chengzhenping@suda.edu.cn (Z.P.C.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 22071168 and 21774082) and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
- DOI：10.1007/s10118-021-2602-3
  中图分类号：
- 收稿：2021-03-31，
  
  修回：2021-4-29，
  
  录用：2021-5-4，
  
  网络首发：2021-07-20，
  
  纸质出版：2021-07-18
- Accepted：
Scan QR Code
Wang, J. Y.; Ni, Y. Y.; Cheng, J. N.; Zhang, L. F.; Cheng, Z. P. Molar mass dispersity control by iodine-mediated reversible-deactivation radical polymerization. Chinese J. Polym. Sci. 2021, 39, 1155–1160

Jin-Ying Wang, Yuan-Yuan Ni, Jian-Nan Cheng, et al. Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1155-1160.
Wang, J. Y.; Ni, Y. Y.; Cheng, J. N.; Zhang, L. F.; Cheng, Z. P. Molar mass dispersity control by iodine-mediated reversible-deactivation radical polymerization. Chinese J. Polym. Sci. 2021, 39, 1155–1160 DOI： 10.1007/s10118-021-2602-3.

Jin-Ying Wang, Yuan-Yuan Ni, Jian-Nan Cheng, et al. Molar Mass Dispersity Control by Iodine-mediated Reversible-deactivation Radical Polymerization[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1155-1160. DOI： 10.1007/s10118-021-2602-3.

摘要

Abstract

Dispersity (

) of polymers has a great effect on the properties of polymeric materials

and therefore how to control

is very important but still a huge challenge in polymer synthesis

especially for reversible-deactivation radical polymerization (RDRP) strategy. Herein

we successfully developed a novel strategy to adjust

of polymers by visible light-controlled reversible complexation mediated living radical polymerization (RCMP) and combination of single-electron transfer-degenerative chain transfer living radical polymerization (SET-DTLRP) at room temperature. In RCMP system

2-iodo-2-methylpropionitrile (CP-I) and ethyl 2-iodo-2-phenylacetate (EIPA) were used as alkyl iodide initiators

by using methyl methacrylate (MMA) as the model monomer and

-butylacrylate (BA) as the end-capping reagent to regulate

of polymers. Subsequently

we successfully prepared the block copolymer PMMA-

-PBA with adjustable

by reactivating the polymer end-chains

via

SET-DTLRP in the presence of copper wire

fully demonstrating that it is a promising strategy that can keep the "living" feature of polymers while regulating their molar mass dispersities easily.

关键词

Keywords

references

Jenkins, A. D.; Jones, R. G.; Moad, G . Terminology for reversible-deactivation radical polymerization previously called "controlled" radical or "living" radical polymerization (IUPAC Recommendations, 2010) . Pure Appl. Chem. , 2009 . 82 483 - 491 . DOI: 10.1351/PAC-REP-08-04-03 http://doi.org/10.1351/PAC-REP-08-04-03 .

Caruso, M. M.; Davis, D. A.; Shen, Q.; Odom, S. A.; Sottos, N. R.; White, S. R.; Moore, J. S . Mechanically-induced chemical changes in polymeric materials . Chem. Rev. , 2009 . 109 5755 - 5798 . DOI: 10.1021/cr9001353 http://doi.org/10.1021/cr9001353 .

Magenau, A. J.; Strandwitz, N. C.; Gennaro, A.; Matyjaszewski, K . Electrochemically mediated atom transfer radical polymerization . Science , 2011 . 332 81 - 84 . DOI: 10.1126/science.1202357 http://doi.org/10.1126/science.1202357 .

Broderick, E. M.; Guo, N.; Vogel, C. S.; Xu, C.; Sutter, J.; Miller, J. T.; Meyer, K.; Mehrkhodavandi, P.; Diaconescu, P. L . Redox control of a ring-opening polymerization catalyst . J. Am. Chem. Soc. , 2011 . 133 9278 - 9281 . DOI: 10.1021/ja2036089 http://doi.org/10.1021/ja2036089 .

Miao, Y. P.; Lyu, J.; Yong, H. Y.; Sigen, A.; Gao, Y. S.; Wang, W. X . Controlled polymerization of methyl methacrylate and styrene via Cu(0)-mediated RDRP by selecting the optimal reaction conditions . Chinese J. Polym. Sci. , 2019 . 37 591 - 597 . DOI: 10.1007/s10118-019-2236-x http://doi.org/10.1007/s10118-019-2236-x .

Destarac, M . Industrial development of reversible-deactivation radical polymerization: is the induction period over? Polym . Chem. , 2018 . 9 4947 - 4967 . .

Ni, Y. Y.; Zhang, L. F.; Cheng, Z. P.; Zhu, X. L . Iodine-mediated reversible-deactivation radical polymerization: a powerful strategy for polymer synthesis . Polym. Chem. , 2019 . 10 2504 - 2515 . DOI: 10.1039/C9PY00091G http://doi.org/10.1039/C9PY00091G .

Corrigan, N.; Jung, K.; Moad, G.; Hawker, C. J.; Matyjaszewski, K.; Boyer, C . Reversible-deactivation radical polymerization (controlled/living radical polymerization): from discovery to materials design and applications . Prog. Polym. Sci. , 2020 . 111 101311 DOI: 10.1016/j.progpolymsci.2020.101311 http://doi.org/10.1016/j.progpolymsci.2020.101311 .

Wang, J. S.; Matyjaszewski, K . Controlled/"living" radical polymerization Halogen atom transfer radical polymerization promoted by a Cu(I)/Cu(II) redox process . Macromolecules , 1995 . 28 7901 - 7910 . .

Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J.; Shooter, A. J . Atom transfer radical polymerization of methyl methacrylate initiated by alkyl bromide and 2-pyridinecarbaldehyde imine copper (I) complexes . Macromolecules , 1997 . 30 2190 - 2193 . DOI: 10.1021/ma961074r http://doi.org/10.1021/ma961074r .

Matyjaszewski, K . Transition metal catalysis in controlled radical polymerization: atom transfer radical polymerization . Chem. Eur. J. , 1999 . 5 3095 - 3102 . DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3095::AID-CHEM3095>3.0.CO;2-# http://doi.org/10.1002/(SICI)1521-3765(19991105)5:11<3095::AID-CHEM3095>3.0.CO;2-# .

Huang, G. C.; Ji, S. X . Effect of Halogen Chain End Fidelity on the Synthesis of Poly(methyl methacrylate- b -styrene) by ATRP . Chinese J. Polym. Sci. , 2018 . 36 1217 - 1224 . DOI: 10.1007/s10118-018-2139-2 http://doi.org/10.1007/s10118-018-2139-2 .

Chiefari, J.; Chong, Y.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P.; Mayadunne, R. T.; Meijs, G. F.; Moad, C. L.; Moad, G . Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process . Macromolecules , 1998 . 31 5559 - 5562 . DOI: 10.1021/ma9804951 http://doi.org/10.1021/ma9804951 .

Moad, G.; Chong, Y.; Postma, A.; Rizzardo, E.; Thang, S. H . Advances in RAFT polymerization: the synthesis of polymers with defined end-groups . Polymer , 2005 . 46 8458 - 8468 . DOI: 10.1016/j.polymer.2004.12.061 http://doi.org/10.1016/j.polymer.2004.12.061 .

Moad, G.; Rizzardo, E.; Thang, S. H . RAFT polymerization and some of its applications . Chem. Asian J. , 2013 . 8 1634 - 1644 . DOI: 10.1002/asia.201300262 http://doi.org/10.1002/asia.201300262 .

Guang, N.; Liu, S.; Li, X.; Tian, L.; Mao, H . Micellization and gelation of the double thermoresponsive ABC-type triblock copolymer synthesized by RAFT . Chinese J. Polym. Sci. , 2016 . 34 965 - 980 . DOI: 10.1007/s10118-016-1817-1 http://doi.org/10.1007/s10118-016-1817-1 .

Boyer, C.; Valade, D.; Lacroix-Desmazes, P.; Ameduri, B.; Boutevin, B . Kinetics of the iodine transfer polymerization of vinylidene fluoride . J. Polym. Sci., Part A: Polym. Chem. , 2006 . 44 5763 - 5777 . DOI: 10.1002/pola.21654 http://doi.org/10.1002/pola.21654 .

Wolpers, A.; Vana, P . UV light as external switch and boost of molar-mass control in iodine-mediated polymerization . Macromolecules , 2014 . 47 954 - 963 . DOI: 10.1021/ma402537r http://doi.org/10.1021/ma402537r .

Tonnar, J.; Lacroix-Desmazes, P . Controlled radical polymerization of styrene by iodine transfer polymerization (ITP) in ab initio emulsion polymerization . Polymer , 2016 . 106 267 - 274 . DOI: 10.1016/j.polymer.2016.08.031 http://doi.org/10.1016/j.polymer.2016.08.031 .

Tezuka, Y. Topological Polymer Chemistry: Progress of Cyclic Polymers in Syntheses, Properties, and Functions . World Scientific: 2013 .

Ionov, L.; Zdyrko, B.; Sidorenko, A.; Minko, S.; Klep, V.; Luzinov, I.; Stamm, M . Gradient polymer layers by “grafting to” approach . Macromol. Rapid Commun. , 2004 . 25 360 - 365 . DOI: 10.1002/marc.200300216 http://doi.org/10.1002/marc.200300216 .

Lu, C.; Wang, C.; Yu, J.; Wang, J.; Chu, F . Metal-free ATRP “grafting from” technique for renewable cellulose graft copolymers . Green Chem. , 2019 . 21 2759 - 2770 . DOI: 10.1039/C9GC00138G http://doi.org/10.1039/C9GC00138G .

Laurent, B. A.; Grayson, S. M . Synthetic approaches for the preparation of cyclic polymers . Chem. Soc. Rev. , 2009 . 38 2202 - 2213 . DOI: 10.1039/b809916m http://doi.org/10.1039/b809916m .

Aksakal, R.; Resmini, M.; Becer, C . Pentablock star shaped polymers in less than 90 minutes via aqueous SET-LRP . Polym. Chem. , 2016 . 7 171 - 175 . DOI: 10.1039/C5PY01623A http://doi.org/10.1039/C5PY01623A .

Matyjaszewski, K . Advanced materials by atom transfer radical polymerization . Adv. Mater. , 2018 . 30 1706441 DOI: 10.1002/adma.201706441 http://doi.org/10.1002/adma.201706441 .

Roy, D.; Giller, C.; Hogan, T.; Roland, C . The rheology and gelation of bidisperse 1, 4-polybutadiene . Polymer , 2015 . 81 111 - 118 . DOI: 10.1016/j.polymer.2015.11.004 http://doi.org/10.1016/j.polymer.2015.11.004 .

Yadav, V.; Hashmi, N.; Ding, W.; Li, T. H.; Mahanthappa, M. K.; Conrad, J. C.; Robertson, M. L . Dispersity control in atom transfer radical polymerizations through addition of phenylhydrazine . Polym. Chem. , 2018 . 9 4332 - 4342 . DOI: 10.1039/C8PY00033F http://doi.org/10.1039/C8PY00033F .

Whitfield, R.; Parkatzidis, K.; Rolland, M.; Truong, N. P.; Anastasaki, A . Tuning dispersity by photoinduced atom transfer radical polymerisation: monomodal distributions with ppm copper concentration . Angew. Chem. Int. Ed. , 2019 . 58 13323 - 13328 . DOI: 10.1002/anie.201906471 http://doi.org/10.1002/anie.201906471 .

Que, Y. R.; Liu, Y. J.; Tan, W.; Feng, C.; Shi, P.; Li, Y. J.; Huang, X. Y . Enhancing photodynamic therapy efficacy by using fluorinated nanoplatform . ACS Macro Lett. , 2016 . 5 168 - 173 . DOI: 10.1021/acsmacrolett.5b00935 http://doi.org/10.1021/acsmacrolett.5b00935 .

Tao, D. L.; Feng, C.; Cui, Y. A.; Yang, X.; Manners, I.; Winnik, M. A.; Huang, X. Y . Monodisperse fiber-like micelles of controlled length and composition with an oligo( p -phenylenevinylene) core via "living" crystallization-driven self-assembly . J. Am. Chem. Soc. , 2017 . 139 7136 - 7139 . DOI: 10.1021/jacs.7b02208 http://doi.org/10.1021/jacs.7b02208 .

Xu, B. B.; Feng, C.; Huang, X. Y . A versatile platform for precise synthesis of asymmetric molecular brush in one shot . Nat. Commun. , 2017 . 8 333 DOI: 10.1038/s41467-017-00365-2 http://doi.org/10.1038/s41467-017-00365-2 .

Feng, C.; Huang, X. Y. . , Polymer brushes: efficient synthesis and applications . Acc. Chem. Res. , 2018 . 51 2314 - 2323 . DOI: 10.1021/acs.accounts.8b00307 http://doi.org/10.1021/acs.accounts.8b00307 .

Gentekos, D. T.; Dupuis, L. N.; Fors, B. P . Beyond dispersity: deterministic control of polymer molecular weight distribution . J. Am. Chem. Soc. , 2016 . 138 1848 - 1851 . DOI: 10.1021/jacs.5b13565 http://doi.org/10.1021/jacs.5b13565 .

Kottisch, V.; Gentekos, D. T.; Fors, B. P . “Shaping” the future of molecular weight distributions in anionic polymerization . ACS Macro Lett. , 2016 . 5 796 - 800 . DOI: 10.1021/acsmacrolett.6b00392 http://doi.org/10.1021/acsmacrolett.6b00392 .

Gentekos, D. T.; Jia, J.; Tirado, E. S.; Barteau, K. P.; Smilgies, D. M.; DiStasio, R. A., Jr.; Fors, B. P . Exploiting molecular weight distribution shape to tune domain spacing in block copolymer thin films . J. Am. Chem. Soc. , 2018 . 140 4639 - 4648 . DOI: 10.1021/jacs.8b00694 http://doi.org/10.1021/jacs.8b00694 .

Gentekos, D. T.; Fors, B. P . Molecular weight distribution shape as a versatile approach to tailoring block copolymer phase behavior . ACS Macro Lett. , 2018 . 7 677 - 682 . DOI: 10.1021/acsmacrolett.8b00295 http://doi.org/10.1021/acsmacrolett.8b00295 .

Corrigan, N.; Almasri, A.; Taillades, W.; Xu, J.; Boyer, C . Controlling molecular weight distributions through photoinduced flow polymerization . Macromolecules , 2017 . 50 8438 - 8448 . DOI: 10.1021/acs.macromol.7b01890 http://doi.org/10.1021/acs.macromol.7b01890 .

Corrigan, N.; Manahan, R.; Lew, Z. T.; Yeow, J.; Xu, J.; Boyer, C . Copolymers with controlled molecular weight distributions and compositional gradients through flow polymerization . Macromolecules , 2018 . 51 4553 - 4563 . DOI: 10.1021/acs.macromol.8b00673 http://doi.org/10.1021/acs.macromol.8b00673 .

Liu, X.; Wang, C. G.; Goto, A . Polymer dispersity control by organocatalyzed living radical polymerization . Angew. Chem. , 2019 . 131 5654 - 5659 . DOI: 10.1002/ange.201814573 http://doi.org/10.1002/ange.201814573 .

Ni, Y.; Tian, C.; Zhang, L.; Cheng, Z.; Zhu, X . Photocontrolled iodine-mediated green reversible-deactivation radical polymerization of methacrylates: effect of water in the polymerization system . ACS Macro Lett. , 2019 . 8 1419 - 1425 . DOI: 10.1021/acsmacrolett.9b00507 http://doi.org/10.1021/acsmacrolett.9b00507 .

Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Weichold, O . Living radical polymerization of vinyl chloride initiated with iodoform and catalyzed by nascent Cu0/tris(2-aminoethyl) amine or polyethyleneimine in water at 25 °C proceeds by a new competing pathways mechanism . J. Polym. Sci., Part A: Polym. Chem. , 2003 . 41 3283 - 3299 . DOI: 10.1002/pola.10937 http://doi.org/10.1002/pola.10937 .

Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S . Ultrafast synthesis of ultrahigh molar mass polymers by metal-catalyzed living radical polymerization of acrylates, methacrylates, and vinyl chloride mediated by SET at 25 °C . J. Am. Chem. Soc. , 2006 . 128 14156 - 14165 . DOI: 10.1021/ja065484z http://doi.org/10.1021/ja065484z .

Kapishon, V.; Whitney, R. A.; Champagne, P.; Cunningham, M. F.; Neufeld, R. J . Polymerization induced self-assembly of alginate based amphiphilic graft copolymers synthesized by single electron transfer living radical polymerization . Biomacromolecules , 2015 . 16 2040 - 2048 . DOI: 10.1021/acs.biomac.5b00470 http://doi.org/10.1021/acs.biomac.5b00470 .

浏览量

152

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Enhancing Processability of Phenylethynyl-terminated Imide Oligomers and Properties of Cured Polyimides via ―CF3 Incorporation

Improvements of Hydrophobicity and Toughness of Epoxy Coatings Modified with Hydroxyl-terminated Fluororubber

2026-9 Contents

Special Topic: Chirality in Polymers

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers