Thiol-acrylate Catalyst Enabled Post-Synthesis Fabrication of Liquid Crystal Actuators

Huan Liang; Ya-Wen Liu; Hong-Tu Xu; Yang Yang; En-Jian He; Zhi-Jun Yang; Yen Wei; Yan Ji

doi:10.1007/s10118-023-3031-2

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Thiol-acrylate Catalyst Enabled Post-Synthesis Fabrication of Liquid Crystal Actuators

RESEARCH ARTICLE | Updated：2023-09-21

- Thiol-acrylate Catalyst Enabled Post-Synthesis Fabrication of Liquid Crystal Actuators
- Chinese Journal of Polymer Science Vol. 41, Issue 10, Pages: 1656-1662(2023)
- Affiliations：
  
  a.K The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China
  b.Institute of Nuclear and New Energy Technology, Tsinghua University, Beijing 100084, China
  c.Department of Chemistry, Center for Nanotechnology and Institute of Biomedical Technology, Chung-Yuan Christian University, Taiwan 32023, China
- Author bio：
  
  jiyan@mail.tsinghua.edu.cn
- Funds：
- DOI：10.1007/s10118-023-3031-2
  CLC：
- Received：28 May 2023，
  
  Revised：2023-7-11，
  
  Accepted：21 July 2023，
  
  Online First：22 August 2023，
  
  Published：01 October 2023
- Accepted：
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Liang, H.; Liu, Y. W.; Xu, H. T.; Yang, Y.; He, E. J.; Yang, Z. J.; Wei, Y.; Ji, Y. Thiol-acrylate catalyst enabled post-synthesis fabrication of liquid crystal actuators. Chinese J. Polym. Sci. 2023, 41, 1656–1662

Huan Liang, Ya-Wen Liu, Hong-Tu Xu, et al. Thiol-acrylate Catalyst Enabled Post-Synthesis Fabrication of Liquid Crystal Actuators[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1656-1662.
Liang, H.; Liu, Y. W.; Xu, H. T.; Yang, Y.; He, E. J.; Yang, Z. J.; Wei, Y.; Ji, Y. Thiol-acrylate catalyst enabled post-synthesis fabrication of liquid crystal actuators. Chinese J. Polym. Sci. 2023, 41, 1656–1662 DOI： 10.1007/s10118-023-3031-2.

Huan Liang, Ya-Wen Liu, Hong-Tu Xu, et al. Thiol-acrylate Catalyst Enabled Post-Synthesis Fabrication of Liquid Crystal Actuators[J]. Chinese Journal of Polymer Science, 2023, 41(10): 1656-1662. DOI： 10.1007/s10118-023-3031-2.

摘要

This work proposed a post-synthesis strategy to fabricate liquid crystal actuators through a volatile catalyst triggering reversible reactions. The method balances the stability and reprogrammability of LCEs crosslinked by extensively used two-stage thiol-acrylate Michael addition and photopolymerization (TAMAP) reaction. It has potential to be extended to other covalent adaptable networks.

Abstract

Synthesizing orientated liquid crystal elastomers (LCEs)

via

the two-stage thiol-acrylate Michael addition and photopolymerization (TAMAP) reaction is extensively used. However

excess acrylates

initiators

and strong stimuli are inevitably involved in the second stage crosslinking. Herein

we simplify the strategy through taking advantage of a volatile alkaline (originally added to catalyze the thiol-acrylate addition in the first crosslinking stage). Without excess functional groups

the residual catalyst after annealing is still enough to trigger reactions of dynamic covalent bonds at a relatively mild temperature (80 °C) to program the alignment of LCEs. The reversible reaction switches off by itself after this process since the catalyst gradually but totally evaporates upon heating. The obtained soft actuators exhibit robust actuation during repeated deformation (over 1000 times). Many shape-morphing modes can be achieved by rationally designing orientation patterns. This strategy not only facilitates the practical synthesis of LCE actuators

but also balances the intrinsic conflict between stability and reprogrammability of exchangeable LCEs. Moreover

the method of applying volatile catalysts has the potential to be extended to other dynamic covalent bonds (DCBs) applied to crosslinked polymer systems.

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references

He,Q.;Wang,Z.;Wang,Y.;Minori,A.;Tolley,M.T.;Cai,S.Electricallycontrolledliquidcrystalelastomer-basedsofttubularactuatorwithmultimodalactuation. Sci. Adv. 2019 , 5 ,eaax5746..

Zhang,J.;Guo,Y.;Hu,W.;Soon,R.H.;Davidson,Z.S.;Sitti,M.Liquidcrystalelastomer-basedmagneticcompositefilmsforreconfigurableshape-morphingsoftminiaturemachines. Adv. Mater. 2021 , 33 ,2006191..

Xia,Y.;Cedillo-Servin,G.;Kamien,R.D.;Yang,S.Guidedfoldingofnematicliquidcrystalelastomersheetsinto3D via patterned1Dmicrochannels. Adv. Mater. 2016 , 28 ,9637−9643..

Jiang,Z.C.;Xiao,Y.Y.;Tong,X.;Zhao,Y.Selectivedecrosslinkinginliquidcrystalpolymeractuatorsforopticalreconfigurationoforigamiandlight-lueledlocomotion. Angew. Chem. Int. Ed. 2019 , 58 ,5332−5337..

Geng,Y.;Kizhakidathazhath,R.;Lagerwall,J.P.F.Robustcholestericliquidcrystalelastomerfibresformechanochromictextiles. Nat. Mater. 2022 , 21 ,1441−1447..

Kim,H.;Gibson,J.;Maeng,J.;Saed,M.O.;Pimentel,K.;Rihani,R.T.;Pancrazio,J.J.;Georgakopoulos,S.V.;Ware,T.H.Responsive,3Delectronicsenabledbyliquidcrystalelastomersubstrates. ACS Appl. Mater. Interfaces 2019 , 11 ,19506−19513..

Li,S.;Bai,H.;Liu,Z.;Zhang,X.;Huang,C.;Wiesner,L.W.;Silberstein,M.;Shepherd,R.F.Digitallightprocessingofliquidcrystalelastomersforself-sensingartificialmuscles. Sci. Adv. 2021 , 7 ,eabg3677..

Liu,H.;Tian,H.;Li,X.;Chen,X.;Zhang,K.;Shi,H.;Wang,C.;Shao,J.Shape-programmable,deformation-locking,andself-sensingartificialmusclebasedonliquidcrystalelastomerandlow-meltingpointalloy. Sci. Adv. 2022 , 8 ,eabn5722..

Liu,Z.;Bisoyi,H.K.;Huang,Y.;Wang,M.;Yang,H.;Li,Q.Thermo-andmechanochromiccamouflageandself-healinginbiomimeticsoftactuatorsbasedonliquidcrystalelastomers. Angew. Chem. Int. Ed. 2022 , 61 ,e202115755..

Palagi,S.;Mark,A.G.;Reigh,S.Y.;Melde,K.;Qiu,T.;Zeng,H.;Parmeggiani,C.;Martella,D.;Sanchez-Castillo,A.;Kapernaum,N.;Giesselmann,F.;Wiersma,D.S.;Lauga,E.;Fischer,P.Structuredlightenablesbiomimeticswimmingandversatilelocomotionofphotoresponsivesoftmicrorobots. Nat. Mater. 2016 , 15 ,647−653..

Cianchetti,M.;Laschi,C.;Menciassi,A.;Dario,P.Biomedicalapplicationsofsoftrobotics. Nat. Rev. Mater. 2018 , 3 ,143−153..

Kim,S.;Laschi,C.;Trimmer,B.Softrobotics:abioinspiredevolutioninrobotics. Trends Biotechnol. 2013 , 31 ,287−294..

Rich,S.I.;Wood,R.J.;Majidi,C.Untetheredsoftrobotics. Nat. Electron. 2018 , 1 ,102−112..

Hartmann,F.;Baumgartner,M.;Kaltenbrunner,M.Becomingsustainable,thenewfrontierinsoftrobotics. Adv. Mater. 2021 , 33 ,2004413..

He,Q.;Wang,Z.;Wang,Y.;Wang,Z.;Li,C.;Annapooranan,R.;Zeng,J.;Chen,R.;Cai,S.Electrospunliquidcrystalelastomermicrofiberactuator. Sci. Robot. 2021 , 6 ,eabi9704..

Herbert,K.M.;Fowler,H.E.;McCracken,J.M.;Schlafmann,K.R.;Koch,J.A.;White,T.J.Synthesisandalignmentofliquidcrystallineelastomers. Nat. Rev. Mater. 2022 , 7 ,23−38..

Kularatne,R.S.;Kim,H.;Boothby,J.M.;Ware,T.H.Liquidcrystalelastomeractuators:synthesis,alignment,andapplications. J. Polym. Sci., Part B: Polym. Phys. 2017 , 55 ,395−411..

Bisoyi,H.K.;Li,Q.Light-drivenliquidcrystallinematerials:fromphoto-inducedphasetransitionsandpropertymodulationstoapplications. Chem. Rev. 2016 , 116 ,15089−15166..

White,T.J.;Broer,D.J.Programmableandadaptivemechanicswithliquidcrystalpolymernetworksandelastomers. Nat. Mater. 2015 , 14 ,1087−1098..

Küpfer,J.;Finkelmann,H.Nematicliquidsinglecrystalelastomers. Makromol. Chem. Rapid Commun. 1991 , 12 ,717−726..

Yakacki,C.M.;Saed,M.;Nair,D.P.;Gong,T.;Reed,S.M.;Bowman,C.N.Tailorableandprogrammableliquid-crystallineelastomersusingatwo-stagethiol-acrylatereaction. RSC Adv. 2015 , 5 ,18997−19001..

Saed,M.O.;Torbati,A.H.;Nair,D.P.;Yakacki,C.M.Synthesisofprogrammablemain-chainliquid-crystallineelastomersusingatwo-stagethiol-acrylatereaction. J. Vis. Exp. 2016 ,e53546..

Bauman,G.E.;McCracken,J.M.;White,T.J.Actuationofliquidcrystallineelastomersatorbelowambienttemperature. Angew. Chem. Int. Ed. 2022 , 61 ,e202202577..

Ma,J.;Yang,Y.;Valenzuela,C.;Zhang,X.;Wang,L.;Feng,W.Mechanochromic,shape-programmableandself-healablecholestericliquidcrystalelastomersenabledbydynamiccovalentboronicesterbonds. Angew. Chem. Int. Ed. 2022 , 61 ,e202116219..

Ube,T.;Kawasaki,K.;Ikeda,T.Photomobileliquid-crystallineelastomerswithrearrangeablenetworks. Adv. Mater. 2016 , 28 ,8212−8217..

Pei,Z.;Yang,Y.;Chen,Q.;Terentjev,E.M.;Wei,Y.;Ji,Y.Mouldableliquid-crystallineelastomeractuatorswithexchangeablecovalentbonds. Nat. Mater. 2014 , 13 ,36−41..

Kotikian,A.;Truby,R.L.;Boley,J.W.;White,T.J.;Lewis,J.A.3Dprintingofliquidcrystalelastomericactuatorswithspatiallyprogramednematicorder. Adv. Mater. 2018 , 30 ,1706164..

Traugutt,N.A.;Mistry,D.;Luo,C.;Yu,K.;Ge,Q.;Yakacki,C.M.Liquid-crystal-elastomer-baseddissipativestructuresbydigitallightprocessing3Dprinting. Adv. Mater. 2020 , 32 ,2000797..

Ambulo,C.P.;Burroughs,J.J.;Boothby,J.M.;Kim,H.;Shankar,M.R.;Ware,T.H.Four-dimensionalprintingofliquidcrystalelastomers. ACS Appl. Mater. Interfaces 2017 , 9 ,37332−37339..

Fang,M.;Liu,T.;Xu,Y.;Jin,B.;Zheng,N.;Zhang,Y.;Zhao,Q.;Jia,Z.;Xie,T.Ultrafastdigitalfabricationofdesignablearchitecturedliquidcrystallineelastomer. Adv. Mater. 2021 , 33 ,2105597..

Jin,B.;Liu,J.;Shi,Y.;Chen,G.;Zhao,Q.;Yang,S.Solvent-assisted4Dprogrammingandreprogrammingofliquidcrystallineorganogels. Adv. Mater. 2022 , 34 ,2107855..

Chen,G.;Jin,B.;Shi,Y.;Zhao,Q.;Shen,Y.;Xie,T.Rapidlyandrepeatedlyreprogrammableliquidcrystallineelastomer via ashapememorymechanism. Adv. Mater. 2022 , 34 ,2201679..

Zou,W.;Lin,X.;Terentjev,E.M.Amine-acrylateliquidsinglecrystalelastomersreinforcedbyhydrogenbonding. Adv. Mater. 2021 , 33 ,e2101955..

Yuan,C.;Roach,D.J.;Dunn,C.K.;Mu,Q.;Kuang,X.;Yakacki,C.M.;Wang,T.J.;Yu,K.;Qi,H.J.3Dprintedreversibleshapechangingsoftactuatorsassistedbyliquidcrystalelastomers. Soft Matter 2017 , 13 ,5558−5568..

Yan,H.;He,Y.;Yao,L.;Wang,X.;Zhang,X.;Zhang,Y.;Han,D.;Li,C.;Sun,L.;Zhang,J.Thermo-crosslinkingassistedpreparationofthiol-acrylatemain-chainliquid-crystallineelastomers. J. Polym. Res. 2022 , 29 ,450..

Zhang,Y.;Wang,Z.;Yang,Y.;Chen,Q.;Qian,X.;Wu,Y.;Liang,H.;Xu,Y.;Wei,Y.;Ji,Y.Seamlessmultimaterial3Dliquid-crystallineelastomeractuatorsfornext-generationentirelysoftrobots. Sci. Adv. 2020 , 6 ,eaay8606..

Chakma,P.;Konkolewicz,D.Dynamiccovalentbondsinpolymericmaterials. Angew. Chem. Int. Ed. 2019 , 58 ,9682−9695..

Wang,Z.;Cai,S.Recentprogressindynamiccovalentchemistriesforliquidcrystalelastomers. J. Mat. Chem. B 2020 , 8 ,6610−6623..

Hanzon,D.W.;Traugutt,N.A.;McBride,M.K.;Bowman,C.N.;Yakacki,C.M.;Yu,K.Adaptableliquidcrystalelastomerswithtransesterification-basedbondexchangereactions. Soft Matter 2018 , 14 ,951−960..

Qian,X.;Chen,Q.;Yang,Y.;Xu,Y.;Li,Z.;Wang,Z.;Wu,Y.;Wei,Y.;Ji,Y.Untetheredrecyclabletubularactuatorswithversatilelocomotionforsoftcontinuumrobots. Adv. Mater. 2018 , 30 ,1801103..

Liang,H.;Wu,Y.;Zhang,Y.;Chen,E.;Wei,Y.;Ji,Y.Elastomersgrowintoactuators. Adv. Mater. 2023 , 35 ,2209853..

Miao,W.;Zou,W.;Luo,Y.;Zheng,N.;Zhao,Q.;Xie,T.Structuraltuningofpolycaprolactonebasedthermadaptshapememorypolymer. Polym. Chem. 2020 , 11 ,1369−1374..

Zhao,Q.;Zou,W.;Luo,Y.;Xie,T.Shapememorypolymernetworkwiththermallydistinctelasticityandplasticity. Sci. Adv. 2016 , 2 ,e1501297..

Jin,B.;Song,H.;Jiang,R.;Song,J.;Zhao,Q.;Xie,T.Programmingacrystallineshapememorypolymernetworkwiththermo-andphoto-reversiblebondstowardasingle-componentsoftrobot. Sci. Adv. 2018 , 4 ,eaao3865..

Chen,Q.;Li,W.;Wei,Y.;Ji,Y.Reprogrammable3Dliquid-crystallineactuatorswithpreciselycontrollablestepwiseactuation. Adv. Intell. Syst. 2021 , 3 ,2000249..

Zhang,B.;Digby,Z.A.;Flum,J.A.;Chakma,P.;Saul,J.M.;Sparks,J.L.;Konkolewicz,D.Dynamicthiol-Michaelchemistryforthermoresponsiverehealableandmalleablenetworks. Macromolecules 2016 , 49 ,6871−6878..

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