Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions

Liang Ding; Juan Li; Rui-Yu Jiang; Ling-Fang Wang; Wei Song; Lei Zhu

doi:10.1007/s10118-019-2263-7

Your Location：

Home >

Browse articles >

Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions

ARTICLE | Updated：2021-02-18

- Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions
- Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions
- Chinese Journal of Polymer Science 2019年37卷第11期页码：1130-1141
- Affiliations：
  
  a.Department of Polymer and Composite Material, School of Materials Engineering, Yancheng Institute of Technology, Yancheng 224051, China
  b.Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA
  c.Jiangsu Collaborative Innovation Center for Ecological Building Material and Environmental Protection Equipments, Yancheng Institute of Technology, Yancheng 224051, China
  d.School of Chemistry and Materials Science, Hubei Engineering University, Hubei Collaborative Innovation Center of Conversion and Utilization for Biomass Resources, Xiaogan 432000, China
- Author bio：
  
  dl1984911@ycit.edu.cn (L.D.)
  jiangry@ycit.cn (R.Y.J.)
  sw121092@ycit.cn (W.S.)
  Lei.zhu@hbeu.edu.cn (L.Z.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21774107, 21774029, and 21801217), the Natural Science Foundation of Jiangsu Province-General Program (No. BK20171273), "Six Talent Peak" High-level Talent Project (JNHB-068), Qing Lan Project of Jiangsu Province, and the Initial Scientific Research Foundation of Yancheng Institute of Technology (No. KJC2014002). The authors also would like to thank Professor Virgil Percec for providing unlimited support and enthusiastic help.
- DOI：10.1007/s10118-019-2263-7
  中图分类号：
- 收稿：2019-02-22，
  
  修回：2019-3-16，
  
  录用：2019-3-25，
  
  网络首发：2019-05-21，
  
  纸质出版：2019-11
- Accepted：
Scan QR Code
Ding, L.; Li, J.; Jiang, R. Y.; Wang, L. F.; Song, W.; Zhu, L. Cu(0) wire-mediated single-electron transfer-living radical polymerization of oligo(ethylene oxide) methyl ether acrylate by selecting the optimal reaction conditions. Chinese J. Polym. Sci. 2019, 37, 1130–1141.

Liang Ding, Juan Li, Rui-Yu Jiang, et al. Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1130-1141.
Ding, L.; Li, J.; Jiang, R. Y.; Wang, L. F.; Song, W.; Zhu, L. Cu(0) wire-mediated single-electron transfer-living radical polymerization of oligo(ethylene oxide) methyl ether acrylate by selecting the optimal reaction conditions. Chinese J. Polym. Sci. 2019, 37, 1130–1141. DOI： 10.1007/s10118-019-2263-7.

Liang Ding, Juan Li, Rui-Yu Jiang, et al. Cu(0) Wire-mediated Single-electron Transfer-living Radical Polymerization of Oligo(ethylene oxide) Methyl Ether Acrylate by Selecting the Optimal Reaction Conditions[J]. Chinese Journal of Polymer Science, 2019, 37(11): 1130-1141. DOI： 10.1007/s10118-019-2263-7.

摘要

Abstract

The efficient Cu(0) wire-catalyzed single-electron transfer-living radical polymerization (SET-LRP) in organic solvents and mixtures of the organic solvents with water has been thoroughly investigated. Oligo(ethylene oxide) methyl ether acrylate was used as an exemplar oligomer monomer to determine the optimum polymerization conditions for rapid

controlled

and quantitative production of well-defined polymers. The effects of Cu(0)-wire length (12.5 or 4.5 cm)

ligand type (tris(dimethylaminoethyl)amine

-TREN

or tris(2-aminoethyl)amine

TREN)

and solvent type (dipolar aprotic solvents

cyclic ethers

alcohol

or acetone) on the polymerization have been evaluated. Kinetic experiments were performed for all polymerizations to assess the " living” behavior of each system employed. Importantly

TREN could be used as a replacement for Me

-TREN in Cu(0) wire-catalyzed SET-LRP of oligomer monomer

which probably provides the most economical and efficient methodology since TREN is 80 times less expensive than Me

-TREN. The high chain-end fidelity of resulting polymer was experimentally verified by thiol-Michael addition reaction at the

-Br chain end and subsequent chain extension with methyl acrylate.

关键词

Keywords

references

Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Monteiro, M.; Barboiu, B.; Weichold, O.; Asandei, A. D.; Mitchell, C. M . Aqueous room temperature metal-catalyzed living radical polymerization of vinyl chloride . J. Am. Chem. Soc. , 2002 . 124 4940 - 4941 . DOI: 10.1021/ja0256055 http://doi.org/10.1021/ja0256055 .

Zhang, Q.; Wilson, P.; Li, Z.; McHale, R.; Godfrey, J.; Anastasaki, A.; Waldron, C.; Haddleton, D. M . Aqueous copper-mediated living polymerization: Exploiting rapid disproportionation of CuBr with Me 6 TREN . J. Am. Chem. Soc. , 2013 . 135 7355 - 7363 . DOI: 10.1021/ja4026402 http://doi.org/10.1021/ja4026402 .

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 - 15165 . DOI: 10.1021/ja065484z http://doi.org/10.1021/ja065484z .

Rosen, B. M.; Percec, V . Single-electron transfer and single-electron transfer degenerative chain transfer living radical polymerization . Chem. Rev. , 2009 . 109 5069 - 5119 . DOI: 10.1021/cr900024j http://doi.org/10.1021/cr900024j .

Zhang, N.; S. Samanta, R.; Rosen, B. M.; Percec, V . Single electron transfer in radical ion and radical-mediated organic, materials and polymer synthesis . Chem. Rev. , 2014 . 114 5848 - 5958 . DOI: 10.1021/cr400689s http://doi.org/10.1021/cr400689s .

Lligadas, G.; Grama, S.; Percec, V . Recent developments in the synthesis of biomacromolecules and their conjugates by SET-LRP . Biomacromolecules , 2017 . 18 1039 - 1063 . DOI: 10.1021/acs.biomac.7b00197 http://doi.org/10.1021/acs.biomac.7b00197 .

Anastasaki, A.; Nikolaou, V.; Nurumbetov, G.; Wilson, P.; Kempe, K.; Quinn, J. F.; Davis, T. P.; Whittaker, M. R.; Haddleton, D. M . Cu(0)-mediated living radical polymerization: A versatile tool for materials synthesis . Chem. Rev. , 2016 . 116 835 - 877 . DOI: 10.1021/acs.chemrev.5b00191 http://doi.org/10.1021/acs.chemrev.5b00191 .

Nguyen, N. H.; Rosen, B. M.; Jiang, X.; Fleischmann, S.; Percec, V . New efficient reaction media for SET-LRP produced from binary mixtures of organic solvents and H 2 O . J. Polym. Sci., Part A: Polym. Chem. , 2009 . 47 5577 - 5590 . DOI: 10.1002/pola.v47:21 http://doi.org/10.1002/pola.v47:21 .

Nguyen, N. H.; Rosen, B. M.; Percec, V . SET-LRP of N , N -dimethylacrylamide and of N -isopropylacrylamide at 25 °C in protic and in dipolar aprotic solvents . J. Polym. Sci., Part A: Polym. Chem. , 2010 . 48 1752 - 1763 . DOI: 10.1002/pola.v48:8 http://doi.org/10.1002/pola.v48:8 .

Leng, X.; Nguyen, N. H.; Beusekom, B.; Wilson, D. A.; Percec, V . SET-LRP of 2-hydroxyethyl acrylate in protic and dipolar aprotic solvents . Polym. Chem. , 2013 . 4 2995 - 3004 . DOI: 10.1039/c3py00048f http://doi.org/10.1039/c3py00048f .

Ding, W.; Lv, C.; Sun, Y.; Liu, X.; Yu, T.; Qu, G.; Luan, H . Synthesis of zwitterionic polymer by SET-LRP at room temperature in aqueous . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 432 - 440 . DOI: 10.1002/pola.v49.2 http://doi.org/10.1002/pola.v49.2 .

Hatano, T.; Rosen, B. M.; Percec, V . SET-LRP of vinyl chloride initiated with CHBr 3 and catalyzed by Cu(0)-wire/TREN in DMSO at 25 °C . J. Polym. Sci., Part A: Polym. Chem. , 2010 . 48 164 - 172 . DOI: 10.1002/pola.v48:1 http://doi.org/10.1002/pola.v48:1 .

Nguyen, N. H.; Levere, M. E.; Percec, V . TREN vs Me 6 -TREN as ligands in SET-LRP of methyl acrylate . J. Polym. Sci., Part A: Polym. Chem. , 2012 . 50 35 - 46 . DOI: 10.1002/pola.v50.1 http://doi.org/10.1002/pola.v50.1 .

Moreno, A.; Grama, S.; Liu, T.; Galià, M.; Lligadas, G.; Percec, V . SET-LRP mediated by TREN in biphasic water-organic solvent mixtures provides the most economical and efficient process . Polym. Chem. , 2017 . 8 7559 - 7574 . DOI: 10.1039/C7PY01841J http://doi.org/10.1039/C7PY01841J .

Moreno, A.; Liu, T.; Ding, L.; Buzzacchera, I.; Galià, M.; Möller, M.; Wilson, C. J.; Lligadas, G.; Percec, V . SET-LRP in biphasic mixtures of fluorinated alcohols with water . Polym. Chem. , 2018 . 9 2313 - 2327 . DOI: 10.1039/C8PY00062J http://doi.org/10.1039/C8PY00062J .

Nicol, E.; Derouineau, T.; Puaud, F.; Zaitsev, A . Synthesis of double hydrophilic poly(ethylene oxide)- b -poly(2-hydroxyethyl acrylate) by single-electron transfer-living radical polymerization . J. Polym. Sci., Part A: Polym. Chem. , 2012 . 50 3885 - 3894 . DOI: 10.1002/pola.v50.18 http://doi.org/10.1002/pola.v50.18 .

Lutz, J. F.; Hoth, A . Preparation of ideal PEG analogues with a tunable thermosensitivity by controlled radical copolymerization of 2-(2-methoxyethoxy)ethyl methacrylate and oligo(ethylene glycol) methacrylate . Macromolecules , 2006 . 39 893 - 896 . DOI: 10.1021/ma0517042 http://doi.org/10.1021/ma0517042 .

Lutz, J. F.; Akdemir, O.; Hoth, A . Point by point comparison of two thermosensitive polymers exhibiting a similar LCST: Is the age of poly(NIPAM) over? . J. Am. Chem. Soc. , 2006 . 128 13046 - 13047 . DOI: 10.1021/ja065324n http://doi.org/10.1021/ja065324n .

Lutz, J. F . Polymerization of oligo(ethylene glycol) (meth)acrylates: Toward new generations of smart biocompatible materials . J. Polym. Sci., Part A: Polym. Chem. , 2008 . 46 3459 - 3470 . DOI: 10.1002/(ISSN)1099-0518 http://doi.org/10.1002/(ISSN)1099-0518 .

Nguyen, N. H.; Leng, X.; Sun, H. J.; Percec, V . SET-LRP of oligo(ethylene oxide) methyl ether methacrylate in the absence and presence of Air . J. Polym. Sci., Part A: Polym. Chem. , 2013 . 51 3110 - 3122 . DOI: 10.1002/pola.26718 http://doi.org/10.1002/pola.26718 .

Nguyen, N. H.; Kulis, J.; Sun, H. J.; Jia, Z.; Beusekom, B.; Levere, M. E.; Wilson, D. A.; Monteiro, M. J.; Percec, V . A comparative study of SET-LRP of oligo(ethylene oxide) methyl ether acrylate in DMSO and in H 2 O . Polym. Chem. , 2013 . 4 144 - 155 . DOI: 10.1039/C2PY20782F http://doi.org/10.1039/C2PY20782F .

Deng, Y.; Li, Y.; Dai, J.; Lang, M.; Huang, X . Functionalization of graphene oxide towards thermo‐sensitive nanocomposites via moderate in situ SET‐LRP . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 4747 - 4755 . DOI: 10.1002/pola.v49.22 http://doi.org/10.1002/pola.v49.22 .

Simula, A.; Nikolaou, V.; Alsubaie, F.; Anastasaki, A.; Haddleton, D. M . The effect of ligand, solvent and Cu(0) source on the efficient polymerization of polyether acrylates and methacrylates in aqueous and organic media . Polym. Chem. , 2015 . 6 5940 - 5950 . DOI: 10.1039/C5PY00887E http://doi.org/10.1039/C5PY00887E .

Ciampolini, M.; Nardi, N . Five-coordinated high-spin complexes of bivalent cobalt, nickel, and copper with tris(2-dimethylaminoethyl)amine . Inorg. Chem. , 1966 . 5 41 - 44 . DOI: 10.1021/ic50035a010 http://doi.org/10.1021/ic50035a010 .

Samanta, S. R.; Percec, V . Synthesis of high molar mass poly( N -butyl acrylate) and poly(2-ethylhexyl acrylate) by SET-LRP in mixtures of fluorinated alcohols with DMSO . Polym. Chem. , 2014 . 5 169 - 174 . DOI: 10.1039/C3PY01008B http://doi.org/10.1039/C3PY01008B .

Enayati, M.; Jezorek, R. L.; Percec, V . A multiple-stage activation of the catalytically inhomogeneous Cu(0) wire used in SET-LRP . Polym. Chem. , 2016 . 7 4549 - 4558 . DOI: 10.1039/C6PY00888G http://doi.org/10.1039/C6PY00888G .

Jezorek, R. L.; Enayati, M.; Smail, R. B.; Lejnieks, J.; Grama, S.; Monteiro, M. J.; Percec, V . The stirring rate provides dramatic acceleration of the ultrafast interfacial SET-LRP in biphasic organic solvent-water mixtures . Polym. Chem. , 2017 . 8 3405 - 3424 . DOI: 10.1039/C7PY00659D http://doi.org/10.1039/C7PY00659D .

Anastasaki, A.; Waldron, C.; Nikolaou, V.; Wilson, P.; McHale, R.; T.; Smith, Haddleton, D. M . Polymerization of long chain[meth]acrylates by Cu(0)-mediated and catalytic chain transfer polymerisation (CCTP): High fidelity end group incorporation and modification . Polym. Chem. , 2013 . 4 4113 - 4119 . DOI: 10.1039/c3py00618b http://doi.org/10.1039/c3py00618b .

Moreno, A.; Liu, T.; Galià, M.; Lligadas, G.; Percec, V . Acrylate-macromonomers and telechelics of PBA by merging biphasic SET-LRP of BA, chain extension with MA and biphasic esterification . Polym. Chem. , 2018 . 9 1961 - 1971 . DOI: 10.1039/C8PY00156A http://doi.org/10.1039/C8PY00156A .

Simula, A.; Nurumbetov, G.; Anastasaki, A.; Wilson, P.; Haddleton, D. M . Synthesis and reactivity of α , ω -homotelechelic polymers by Cu(0)-mediated living radical polymerization . Eur. Polym. J. , 2015 . 62 294 - 303 . DOI: 10.1016/j.eurpolymj.2014.07.014 http://doi.org/10.1016/j.eurpolymj.2014.07.014 .

Simula, A.; Nikolaou, V.; Anastasaki, A.; Alsubaie, F.; Nurumbetov, G.; Wilson, P.; Kempe, K.; Haddleton, D. M . Synthesis of well-defined α , ω -telechelic multiblock copolymers in aqueous medium: In situ generation of α , ω -diols . Polym. Chem. , 2015 . 6 2226 - 2233 . DOI: 10.1039/C4PY01802H http://doi.org/10.1039/C4PY01802H .

浏览量

218

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

4-Bromophthalic Anhydride-based Polyesters as a Versatile Modified Platform

Unique Damping Properties of Modified Eucommia Ulmoides Gum Bearing Polar and Branched Pendants

Preparation and Characterization of UV-absorbing PVDF Membranes via Pre-irradiation Induced Graft Polymerization

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

Advances in Polymer-based Circularly Polarized Luminescent Materials