Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers <italic style="font-style: italic">via</italic> Successive Flow START Polymerization and Cu(0)-Mediated RDRP

Peng Wang; Shuai-Jie Chen; Jian-Nan Cheng; Wei-Wei He; Li-Fen Zhang; Zhen-Ping Cheng

doi:10.1007/s10118-023-3003-6

Your Location：

Home >

Browse articles >

Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP

RAPID COMMUNICATION | Updated：2023-07-18

- Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP
- Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP
- 高分子科学（英文版） 2023年41卷第8期页码：1155-1161
- Affiliations：
  
  a.State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials; Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application; Suzhou key Laboratory of Macromolecular Design and Precision Synthesis; College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
  b.State Key Laboratory of Radiation Medicine and Protection, School of Radiological and Interdisciplinary Sciences (RADX), Soochow University, Collaborative Innovation Center of Radiological Medicine of Jiangsu Higher Education Institutions, Suzhou 215123, China
- Author bio：
  
  wwhe@suda.edu.cn (W.W.H.)
  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, 21971178 and 21674071) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-023-3003-6.
- DOI：10.1007/s10118-023-3003-6
  中图分类号：
- 收稿：2023-04-22，
  
  修回：2023-5-14，
  
  录用：2023-5-16，
  
  网络首发：2023-06-12，
  
  纸质出版：2023-08-01
- Accepted：
Scan QR Code
Wang, P.; Chen, S. J.; Cheng, J. N.; He, W. W.; Zhang, L. F.; Cheng, Z. P. Continuous synthesis of main-chain-type fluorinated graft copolymers via successive flow START polymerization and Cu(0)-mediated RDRP. Chinese J. Polym. Sci. 2023, 41, 1155–1161

Peng Wang, Shuai-Jie Chen, Jian-Nan Cheng, et al. Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1155-1161. DOI: 10.1007/s10118-023-3003-6.
Wang, P.; Chen, S. J.; Cheng, J. N.; He, W. W.; Zhang, L. F.; Cheng, Z. P. Continuous synthesis of main-chain-type fluorinated graft copolymers via successive flow START polymerization and Cu(0)-mediated RDRP. Chinese J. Polym. Sci. 2023, 41, 1155–1161 DOI： 10.1007/s10118-023-3003-6.

Peng Wang, Shuai-Jie Chen, Jian-Nan Cheng, et al. Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP[J]. Chinese Journal of Polymer Science, 2023, 41(8): 1155-1161. DOI: 10.1007/s10118-023-3003-6. DOI：

摘要

Abstract

Fluorinated polymers are receiving more and more attention worldwide due to their unique chemical properties

and modified fluorinated polymers with different topologies are persued for enriching and enhancing their performance in a variety of application fields. In this work

main-chain-type semifluorinated graft copolymers are produced steadily in continuous tube reactors

via

photocontrolled step transfer-addition and radical-termination (START) polymerization and Cu(0)-mediated reversible deactivation radical polymerization (Cu(0)-RDRP) at room temperature for the first time. Specifically

semifluorinated alternating copolymer (AB)

B is prepared by START polymerization of 1

6-diiodoperfluorohexane (A) and 1

7-octadiene (B) in the first quartz pipeline under irradiation with purple LED light at 20 °C. The (AB)

B with periodic C―I bonds is then flowed into the second copper pipeline directly and acts as the macroinitiators for Cu(0)-RDRP of methyl acrylate (MA) to obtain corresponding graft copolymer (AB)

B-

-PMA. This work provides a new strategy for continuous synthesis of fluorinated graft copolymer materials.

关键词

Keywords

references

Chambers,R.D. Fluorine in organic chemistry .Wiley-Interscience,NewYork, 1973 ..

Kirsch,P. Modern fluoroorganic chemistry .Wiley-VCH,NewYork, 2004 ..

Yao,W.;Li,Y.;Huang,X.Fluorinatedpoly(meth)acrylate:Synthesisandproperties. Polymer 2014 , 55 ,6197−6211..

Tan,J.,Liu,W.;Wang,Z.WaterborneUV-curablecomb-shaped(meth)acrylategraftcopolymercontaininglongfluorinatedand/orpolysiloxanesidechains. RSC Adv. 2016 , 6 ,34364−34375..

Dargaville,T.R.;George,G.A.;Hill,D.J.T.;Whittaker,A.K.Highenergyradiationgraftingoffluoropolymers. Prog. Polym. Sci. 2003 , 28 ,1355−1376..

Tesch,M.;Hepperle,J.A.M.;Klaasen,H.;Letzel,M.;Studer,A.Alternatingcopolymerizationbynitroxide-mediatedpolymerizationandsubsequentorthogonalfunctionalization. Angew. Chem. Int. Ed. 2015 , 54 ,5054−5059..

Xu,B.B.;Liu,Y.J.;Sun,X.W.;Hu,J.H.;Shi,P.;Huang,X.Y.Semifluorinatedsynergisticnonfouling/fouling-releasesurface. ACS Appl. Mater. Interfaces 2017 , 9 ,16517−16523..

Jia,M.C.;Li,Y.J.;He,C.Q.;Huang,X.Y.Solubleperfluorocyclobutylarylether-basedpolyimideforhigh-performancedielectricmaterial. ACS Appl. Mater. Interfaces 2016 , 8 ,26352−26358..

Zaggia,A.;Ameduri,B.Recentadvancesonsynthesisofpotentiallynon-bioaccumulablefluorinatedsurfactants. Curr. Opin. Colloid In. 2012 , 17 ,188−195..

Wu,J.S.;Hou,W.M.;Liu,Z.J.Shi,Y.;Chen,Y.M.Mainchainsemifluorinatedpolymerswithultrahighmolecularweight via reaction-enhancedreactivityofintermediate(RERI)mechanism. Chinese J. Polym. Sci. 2023 , 5 ,760−767..

Borkar,S.;Sen,A.;Shallenberger,J.R.Alternatingpolyester/fluoroalkenecopolymers:Combininghighhydrophobicitywithdegradability. J. Polym. Sci., Part A: Polym. Chem. 2006 , 44 ,1225−1232..

Jiang,K.;Han,S.;Ma,M.;Zhang,L.;Zhao,Y.;Chen,M.Photoorganocatalyzedreversible-deactivationalternatingcopolymerizationofchlorotrifluoroethyleneandvinylethersunderambientconditions:facileaccesstomain-chainfluorinatedcopolymers. J. Am. Chem. Soc. 2020 , 142 ,7108−7115..

Lee,J.;Lopez,G.;Améduri,B.;Seo,M.Synthesisofheterograftcopolymerswithasemifluorinatedbackbonebycombinationofgrafting-throughandgrafting-frompolymerizations. Macromolecules 2020 , 53 ,2811−2821..

Deng,J.R.;Zhao,C.L.;Wei,Z.T.;Wu,Y.X.Amphiphilicgraftcopolymersofhydroxypropylcellulosebackbonewithnonpolarpolyisobutylenebranches. Chinese J. Polym. Sci. 2021 , 39 ,1029−1039..

Xu,T.C.;Yin,H.N.;Li,X.L.;Zhang,L.F.;Cheng,Z.P.;Zhu,X.L.Steptransfer-additionandradical-termination(START)polymerizationof α,ω -unconjugateddienesunderirradiationofblueledlight. Macromol. Rapid Commun. 2017 , 38 ,1600587..

Xu,T.C.;Tu,K.;Cheng,J.N.;Ni,Y.Y.;Zhang,L.F.;Cheng,Z.P.;Zhu,X.L.Organocatalyticapproachtofunctionalsemifluorinatedpolymersdrivenbyvisiblelight. Macromol. Rapid Commun. 2018 , 39 ,1800151..

Cheng,J.N.;Tu,K.;He,E.J.;Wang,J.Y.;Zhang,L.F.;Cheng,Z.P.;Zhu,X.L.Photocontrollediodine-mediatedreversible-deactivationradicalpolymerizationwithasemifluorinatedalternatingcopolymerasthemacroinitiator. Polym. Chem. 2020 , 11 ,7497−7505..

Tu,K.;Liu,C.;He,E.J.;Cheng,J.N.;Zhang,L.F.;Cheng,Z.P.Reduction-inducedcrystallization-drivenself-assemblyofmain-chain-typealternatingcopolymers:transformationfrom1dlinesto2Dplatelets. ACS Macro Lett. 2021 , 10 ,564−569..

Wang,J.Y.;Cheng,J.N.;Tu,K.;Wang,Y.X.;Yu,Q.;Zhang,L.F.;Cheng,Z.P.Fluorinatedreversedmicellesbypolymerization-inducedself-assemblywithmain-chain-typesemifluorinatedalternatingcopolymer. Eur. Polym. J. 2022 , 178 ,111493..

Que,Y.R.;Liu,Y.J.;Tan,W.;Feng,C.;Shi,P.;Li,Y.J.;Huang,X.Y.Enhancingphotodynamictherapyefficacybyusingfluorinatednanoplatform. ACS Macro Lett. 2016 , 5 ,168−173..

Banerjee,S.;Domenichelli,I.;Ameduri,B.Nitroxide-mediatedalternatingcopolymerizationofvinylacetatewith tert -butyl-2-trifluoromethacrylateusingaSG1-basedalkoxyamine. ACS Macro Lett. 2016 , 5 ,1232−1236..

Zhao,Y.;Chen,Y.;Zhou,H.Controlledradicalcopolymerizationoffluoroalkenesbyusinglight-drivenredox-relaycatalysis. Nat. Synth. 2023 ,doi.org/10.1038/s44160-023-00284-9..

Wang,W.;Yan,D.;Bratton,D.;Howdle,S.M.;Wang,Q.;Lecomte,P.Chargetransfercomplexinimer:afacileroutetodendriticmaterials. Adv. Mater. 2003 , 15 ,1348−1352..

Wang,Y.X.;Tu,K.;Cheng,J.N.;He,E.J.;Wang,J.Y.,Zhang,L.F.;Cheng,Z.P.Facilephotochemicalsynthesisofmain-chain-typesemifluorinatedalternatingcopolymerscatalyzedbyconventionalaminesorhalidesalts. Chem. Commun. 2021 , 57 ,11354−11357..

He,E.J.;Tu,K.;Cheng,J.N.;Wang,Y.X.;Lu,H.J.;Zhang,L.F.;Cheng,Z.P.Synthesisandphasebehaviorof(semifluorinatedalkane)-basedside-chainliquidcrystallinecopolymers. Macromol. Rapid Commun. 2022 , 43 ,2200266..

Percec,V.;Popov,A.V.;Ramirez-Castillo,E.;Weichold,O.LivingradicalpolymerizationofvinylchlorideinitiatedwithiodoformandcatalyzedbynascentCu0/tris(2-aminoethyl)amineorpolyethyleneimineinwaterat25°Cproceedsbyanewcompetingpathwaysmechanism. J. Polym. Sci., Part A: Polym. Chem. 2003 , 41 ,3283−3299..

Rosen,B.M.;Percec,V.Single-electrontransferandsingle-electrontransferdegenerativechaintransferlivingradicalpolymerization. Chem. Rev. 2009 , 109 ,5069−5119..

Anastasaki,A.;Nikolaou,V.;Nurumbetov,G.;Wilson,P.;Kempe,K.;Quinn,J.F.;Davis,T.P.;Whittaker,M.R.;Haddleton,D.M.Cu(0)-mediatedlivingradicalpolymerization:aversatiletoolformaterialssynthesis. Chem. Rev. 2016 , 116 ,835−877..

Feng,C.;Huang,X.Y.Polymerbrushes:efficientsynthesisandapplications. Acc. Chem. Res. 2018 , 51 ,2314−2323..

Xu,B.B.;Feng,C.;Huang,X.Y.Aversatileplatformforprecisesynthesisofasymmetricmolecularbrushinoneshot. Nat. Commun. 2017 , 8 ,333..

Percec,V.;Guliashvili,T.;Ladislaw,J.S.;Wistrand,A.;Stjerndahl,A.;Sienkowska,M.J.;Monteiro,M.J.;Sahoo,S.Ultrafastsynthesisofultrahighmolarmasspolymersbymetal-catalyzedlivingradicalpolymerizationofacrylates,methacrylates,andvinylchloridemediatedbySETat25°C. J. Am. Chem. Soc. 2006 , 128 ,14156−14165..

Whitfield,R.;Anastasaki,A.;Nikolaou,V.;Jones,G.R.;Engelis,N.G.;Discekici,E.H.;Fleischmann,C.;Willenbacher,J.,Hawker,C.J.;Haddleton,D.M.Universalconditionsforthecontrolledpolymerizationofacrylates,methacrylates,andstyrene via Cu(0)-RDRP. J. Am. Chem. Soc. 2017 , 139 ,1003−1010..

Zhang,Y.Z.;Wang,Y.;Matyjaszewski,K.ATRPofMethylAcrylatewithmetalliczinc,magnesium,andironasreducingagentsandsupplementalactivators. Macromolecules 2011 , 44 ,683−685..

Mohammad,S.A.;Shingdilwar,S.;Banerjee,S.Recoverableandrecyclablenickel–cobaltmagneticalloynanoparticlecatalyzedreversibledeactivationradicalpolymerizationofmethylmethacrylateat25°C. Polym. Chem. 2020 , 11 ,287−291..

Aksakal,S.;Beyer,V.P.;Aksakal,R.;Becer,C.R.CoppermediatedRDRPofthioacrylatesandtheircombinationwithacrylatesandacrylamides. Polym. Chem. 2019 , 10 ,6622−6629..

Liarou,E.;Whitfield,R.;Anastasaki,A.;Engelis,N.G.;Jones,G.R.;Velonia,K.;Haddleton,D.M.Copper-mediatedpolymerizationwithoutexternaldeoxygenationoroxygenscavengers. Angew. Chem. Int. Ed. 2018 , 57 ,8998−9002..

Jones,G.R.;Anastasaki,A.;Whitfield,R.;Engelis,N.;Liarou,E.;Haddleton,D.M.Copper-mediatedreversibledeactivationradicalpolymerizationinaqueousmedia. Angew. Chem. Int. Ed. 2018 , 57 ,10468−10482..

Peng,J.Y.;Tian,C.;Zhang,L.F.;Cheng,Z.P.The in situ formationofnanoparticles via RAFTpolymerization-inducedself-assemblyinacontinuoustubularreactor. Polym. Chem. 2017 , 8 ,1495−1506..

Chan,N.;Cunningham,M.F.;Hutchinson,R.A.Continuouscontrolledradicalpolymerizationofmethylacrylateinacoppertubularreactor. Macromol. Rapid Commun. 2011 , 32 ,604−609..

ElAchi,N.;Bakkour,Y.;Adhami,W.;Molina,J.;Penhoat,M.;Azaroual,N.;Chausset-Boissarie,L.;Rolando,C.Metal-freeATRPcatalyzedbyvisiblelightincontinuousflow. Front Chem. 2020 , 8 ,740..

Li,M.,Zhang,Y.;Zhang,J.;Peng,M.;Yan,L.;Tang,Z.;Wu,Q.Continuousgas–liquid–solidslugflowforsustainableheterogeneouslycatalyzedPET-RAFTpolymerization. Ind. Eng. Chem. Res. 2021 , 60 ,5451−5462..

Liao,D.;Pang,W.;Bashir,M.S.;Chen,C.Acontinuousflow-throughstrategytoproducehighlyisotacticpoly(isobutylvinylether) via cationicpolymerization. Polym. Chem. 2022 , 13 ,5068−5072..

Chen,K.;Zhou,Y.;Han,S.;Liu,Y.;Chen,M.Main-chainfluoropolymerswithalternatingsequencecontrol via light-drivenreversible-deactivationcopolymerizationinbatchandflow. Angew. Chem. Int. Ed. 2022 , 61 ,e202116135..

Zhong,F.;Zhou,Y.;Chen,M.Theinfluenceofmixingonchainextensionbyphoto-controlled/livingradicalpolymerizationundercontinuous-flowconditions. Polym. Chem. 2019 , 10 ,4879−4886..

Peng,J.Y.;Xu,Q.H.;Ni,Y.Y.;Zhang,L.F.;Cheng,Z.P.;Zhu,X.L.VisiblelightcontrolledaqueousRAFTcontinuousflowpolymerizationwithoxygentolerance. Polym. Chem. 2019 , 10 ,2064−2072..

Chen,R.;Jiang,X.;Lu,G.L.;Liu,W.B.;Jin,W.Z.;Tian,G.J.;Huang,X.Y.Awell-definedthermo-andpH-responsivedoublehydrophilicgraftcopolymerbearingpyridine-containingbackbone. Polym. Chem. 2022 , 13 ,2791−2802..

浏览量

199

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

3D Printing of Biocompatible Nanocellulose-reinforced Hydrogels via Polymerizable Ternary Deep Eutectic Solvent Assistance

Photocontrolled Solution [2+2] Polymerization of p-Phenylenediacrylate and Depolymerization

One-pot and One-step Cu(0)-mediated Reversible-Deactivation Radical Polymerization of N-Isopropylacrylamide (NIPAM) in Water

End-group and Side-chain Dual-engineering of Selenium-fused Acceptors for 20.08% Efficiency Polymer Solar Cells with Low Energy Loss

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

Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP

Continuous Synthesis of Main-Chain-type Fluorinated Graft Copolymers via Successive Flow START Polymerization and Cu(0)-Mediated RDRP

DOI：10.1007/s10118-023-3003-6

摘要

Abstract

关键词

Keywords

references