Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction

Chun-Yan Yu; Jia-Hui Mu; Yun-Lei Fu; Yun-Chao Zhang; Ji-Shu Han; Rui-Yang Zhao; Jia Zhao; Zi-Hao Wang; Zhong-Cheng Zhao; Wei-Jun Li; Fu-Sheng Liu

doi:10.1007/s10118-021-2504-4

Your Location：

Home >

Browse articles >

Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction

ARTICLE | Updated：2020-10-10

- Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction
- Chinese Journal of Polymer Science Vol. 39, Issue 4, Pages: 417-424(2021)
- Affiliations：
  
  a.State Key Laboratory Base of Eco-chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  b.Taishan Scholar Advantage and Characteristic Discipline Team of Eco Chemical Process and Technology, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
  c.State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
- Author bio：
  
  jishu_han@163.com (J.S.H.)
  zhaoruiyang1985@163.com (R.Y.Z.)
- Funds：
- DOI：10.1007/s10118-021-2504-4
  CLC：
- Received：23 July 2020，
  
  Revised：2020-8-14，
  
  Accepted：19 August 2020，
  
  Online First：10 October 2020，
  
  Published：01 January 2021
- Accepted：
Scan QR Code
Yu, C. Y.; Mu, J. H.; Fu, Y. L.; Zhang, Y. C.; Han, J. S.; Zhao, R. Y.; Zhao, J.; Wang, Z. H.; Zhao, Z. C.; Li, W. J.; Liu, F. S. Azobenzene based photo-responsive mechanical actuator fabricated by intermolecular H-bond interaction. Chinese J. Polym. Sci. 2021, 39, 417–424

Chun-Yan Yu, Jia-Hui Mu, Yun-Lei Fu, et al. Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction[J]. Chinese Journal of Polymer Science, 2021, 39(4): 417-424.
Yu, C. Y.; Mu, J. H.; Fu, Y. L.; Zhang, Y. C.; Han, J. S.; Zhao, R. Y.; Zhao, J.; Wang, Z. H.; Zhao, Z. C.; Li, W. J.; Liu, F. S. Azobenzene based photo-responsive mechanical actuator fabricated by intermolecular H-bond interaction. Chinese J. Polym. Sci. 2021, 39, 417–424 DOI： 10.1007/s10118-021-2504-4.

Chun-Yan Yu, Jia-Hui Mu, Yun-Lei Fu, et al. Azobenzene Based Photo-responsive Mechanical Actuator Fabricated by Intermolecular H-bond Interaction[J]. Chinese Journal of Polymer Science, 2021, 39(4): 417-424. DOI： 10.1007/s10118-021-2504-4.

摘要

Abstract

Photo-responsive mechanical actuator is a class of stimuli-responsive materials transferring light to mechanical energy through macroscopic transformation. To fabricate photo-responsive mechanical actuator

soft polymeric materials crosslinked with functional bridging structures are desired. Supramolecular interaction is a relatively common way to fabricate crosslinked materials due to its excellent self-assembly performance. And azobenzene and derivatives are ideal candidates of photo-responsive materials because of the unique photo-induced

trans-cis

isomerization. Here

a new kind of crosslinked materials based on supramolecular interaction between 4

-dihydroxyazobenzene and chitosan is reported. Under 355 nm irradiation

the macroscopic bending of polymeric materials occurs rapidly due to the photo-isomerization of 4

-dihydroxyazobenzene. Meanwhile

the photo-responsive mechanical actuator can also lift weight which is up to 200 times that of the actuator itself

and convert energy from light to mechanical work efficiently. This report suggests a new kind of photo-responsive actuator based on supramolecular interaction and may be helpful to contribute a theoretical basis to the design and synthesis of photo-responsive mechanical actuator suitable for large-scale manufacturing industrialization in future.

关键词

Keywords

references

Hirokawa, N. . Kinesin and dynein superfamily proteins and the mechanism of organelle transport . Science , 1998 . 279 519 - 526 . DOI: 10.1126/science.279.5350.519 http://doi.org/10.1126/science.279.5350.519 .

Vale, R.; Milligan, R. . The way things move: looking under the hood of molecular motor proteins . Science , 2000 . 288 88 - 95 . DOI: 10.1126/science.288.5463.88 http://doi.org/10.1126/science.288.5463.88 .

Majidi, C. . Soft robotics: a perspective-current trends and prospects for the future . Soft Robot , 2014 . 1 5 - 11 . DOI: 10.1089/soro.2013.0001 http://doi.org/10.1089/soro.2013.0001 .

Yamauchi, K.; Takashima, Y.; Hashidzume, A.; Yamaguchi, H.; Harada, A. . Switching between supramolecular dimer and nonthreaded supramolecular self-assembly of stilbene amide- α -cyclodextrin by photoirradiation . J. Am. Chem. Soc. , 2008 . 130 5024 - 5025 . DOI: 10.1021/ja7113135 http://doi.org/10.1021/ja7113135 .

Tsuda, S.; Aso, Y.; Kaneda, T. . Linear oligomers composed of a photochromically contractible and extendable Janus [2]rotaxane . Chem. Commun. , 2006 . 29 3072 - 3074 . .

Liu, Y. Y.; Wu, W.; Wei, J.; Yu, Y. L. . Visible light responsive liquid crystal polymers containing reactive moieties with good processability . ACS Appl. Mater. Interfaces , 2017 . 9 782 - 789 . DOI: 10.1021/acsami.6b11550 http://doi.org/10.1021/acsami.6b11550 .

Stoychev, G.; Kirillova, A. . Light-responsive shape-changing polymers . Adv. Opt. Mater. , 2019 . 7 1 - 30 . .

Liu, J. Q.; Li, A. H.; Tang, J. G.; Wang, R.; Kong, N.; Davis, T. . Thermoresponsive silver/polymer nanohybrids with switchable metal enhanced fluorescence . Chem. Commun. , 2012 . 48 4680 - 4682 . DOI: 10.1039/c2cc18069c http://doi.org/10.1039/c2cc18069c .

Yoshida, R.; Uchida, K.; Kaneko, Y.; Sakai, K.; Kikuchi, A.; Sakurai, Y.; Okano, T. . Comb-type grafted hydrogels with rapid deswelling response to temperature changes . Nature , 1995 . 374 240 - 242 . DOI: 10.1038/374240a0 http://doi.org/10.1038/374240a0 .

Hu, Z. B.; Lu, X. H.; Gao, J. . Hydrogel opals . Adv. Mater. , 2001 . 13 1708 - 1712 . DOI: 10.1002/1521-4095(200111)13:22<1708::AID-ADMA1708>3.0.CO;2-L http://doi.org/10.1002/1521-4095(200111)13:22<1708::AID-ADMA1708>3.0.CO;2-L .

Bowen, J.; Rose, M.; Konda, A.; Morin, S. . Surface molding of microscale hydrogels with microactuation functionality . Angew. Chem. Int. Ed. , 2018 . 57 1236 - 1240 . DOI: 10.1002/anie.201710612 http://doi.org/10.1002/anie.201710612 .

Ma, Y.; Zhang, Y. Y.; Wu, B. S.; Sun, W. P.; Li, Z. G.; Sun, J. Q. . Polyelectrolyte multilayer films for building energetic walking devices . Angew. Chem. Int. Ed. , 2011 . 50 6254 - 6257 . DOI: 10.1002/anie.201101054 http://doi.org/10.1002/anie.201101054 .

Chen, P. N.; Xu, Y. F.; He, S. S.; Sun, X. M.; Pan, S. W.; Deng, J.; Chen, D. Y.; Peng, H. S. . Hierarchically arranged helical fibre actuators driven by solvents and vapours . Nat. Nanotechnol. , 2015 . 10 1077 - 1083 . DOI: 10.1038/nnano.2015.198 http://doi.org/10.1038/nnano.2015.198 .

Palleau, E.; Morales, D.; Dickey, M.; Velev, O. . Reversible patterning and actuation of hydrogels by electrically assisted ionoprinting . Nat. Commun. , 2013 . 4 2257 DOI: 10.1038/ncomms3257 http://doi.org/10.1038/ncomms3257 .

Must, I.; Kaasik, F.; Poldsalu, I.; Mihkels, L.; Johanson, U.; Punning, A.; Aabloo, A. . Ionic and capacitive artificial muscle for biomimetic soft robotics . Adv. Eng. Mater. , 2015 . 17 84 - 94 . DOI: 10.1002/adem.201400246 http://doi.org/10.1002/adem.201400246 .

Wu, J.; Leung, K.; Benitez, D.; Han, J.; Cantrill, S.; Fang, L.; Stoddart, J. . An acid-base-controllable [c2]daisy chain . Angew. Chem. Int. Ed. , 2008 . 47 7470 - 744 . DOI: 10.1002/anie.200803036 http://doi.org/10.1002/anie.200803036 .

Coutrot, F.; Romuald, C.; Busseron, E. . A new pH-switchable dimannosyl[c2]daisy chain molecular machine . Org. Lett. , 2008 . 10 3741 - 3744 . DOI: 10.1021/ol801390h http://doi.org/10.1021/ol801390h .

Bruns, C.; Frasconi, M.; Iehl, J.; Hartlieb, K.; Schneebeli, S.; Cheng, C.; Stupp, S.; Stoddart, J. . Redox switchable daisy chain rotaxanes driven by radical-radical interactions . J. Am. Chem. Soc. , 2014 . 136 4714 - 4723 . DOI: 10.1021/ja500675y http://doi.org/10.1021/ja500675y .

Bruns, C.; Li, J.; Frasconi, M. . An electrochemically and thermally switchable donor-acceptor[c2]daisy chain rotaxane . Angew. Chem. Int. Ed. , 2014 . 53 1953 - 1958 . DOI: 10.1002/anie.201308498 http://doi.org/10.1002/anie.201308498 .

Stoychev, G.; Kirillova, A.; Ionov, L. . Light-responsive shape-changing polymers . Adv. Optical. Mater. , 2019 . 7 1 - 30 . .

Jiang, H.; Kelch, S.; Lendlein, A. . Polymers move in response to light . Adv. Mater. , 2006 . 18 1471 - 1475 . DOI: 10.1002/adma.200502266 http://doi.org/10.1002/adma.200502266 .

Habault, D.; Zhang, H.; Zhao, Y. . Light-triggered self-healing and shape-memory polymers . Chem. Soc. Rev. , 2013 . 42 7244 - 7256 . DOI: 10.1039/c3cs35489j http://doi.org/10.1039/c3cs35489j .

Han, D.; Zhang, Y.; Ma, J.; Liu, Y.; Han, B.; Sun, H. . Light-mediated manufacture and manipulation of actuators . Adv. Mater. , 2016 . 28 8328 - 8343 . DOI: 10.1002/adma.201602211 http://doi.org/10.1002/adma.201602211 .

Bushuyev, O.; Aizawa, M.; Shishido, A.; Barrett, C. . Shape-shifting azo dye polymers: towards sunlight-driven molecular devices . Macromol. Rapid Commun. , 2018 . 39 1700253 DOI: 10.1002/marc.201700253 http://doi.org/10.1002/marc.201700253 .

Jochum, F.; Theato, P. . Temperature-and light-responsive smart polymer materials . Chem. Soc. Rev. , 2013 . 42 7468 - 7483 . DOI: 10.1039/C2CS35191A http://doi.org/10.1039/C2CS35191A .

Natansohn, A.; Rochon, P. . Photoinduced motions in azo-containing polymers . Chem. Rev. , 2002 . 102 4139 - 4176 . DOI: 10.1021/cr970155y http://doi.org/10.1021/cr970155y .

Wei, J.; Yu, Y. L. . Photodeformable polymer gels and crosslinked liquid-crystalline polymers . Soft Matter , 2012 . 8 8050 - 8059 . DOI: 10.1039/c2sm25474c http://doi.org/10.1039/c2sm25474c .

Liu, D.; Broer, D. . Self-assembled dynamic 3D fingerprints in liquid-crystal coatings towards controllable friction and adhesion . Angew. Chem. Int. Ed. , 2014 . 53 4542 - 4546 . DOI: 10.1002/anie.201400370 http://doi.org/10.1002/anie.201400370 .

Zhao, R. Y.; Zhan, X. P.; Yao, L.; Chen, Q. D.; Xie, Z. Q.; Ma, Y. G. . Electrochemical deposition of azobenzene-containing network films with high-contrast and stable photoresponse . Macromol. Rapid Commun. , 2016 . 37 610 - 615 . DOI: 10.1002/marc.201500646 http://doi.org/10.1002/marc.201500646 .

Zhao, R. Y.; Zhan, X. P.; Yao, J.; Sun, G. N.; Chen, Q. D.; Xie, Z. Q.; Ma, Y. G. . Reversible photo-controlled mass transfer in a photo-responsive conjugated main-chain polymer film for high contrast surface patterning . Polym. Chem. , 2013 . 4 5382 - 5386 . DOI: 10.1039/c3py00770g http://doi.org/10.1039/c3py00770g .

Yu, Y. L.; Nakano, M.; Ikeda, T. . Photomechanics: directed bending of a polymer film by light . Nature , 2003 . 425 145 - 145 . DOI: 10.1038/425145a http://doi.org/10.1038/425145a .

Lopez, M.; Finkelmann, H.; Muhoray, P.; Shelley, M. . Fast liquid-crystal elastomer swims into the dark . Nat. Mater. , 2004 . 3 307 - 310 . DOI: 10.1038/nmat1118 http://doi.org/10.1038/nmat1118 .

Zeng, H.; Wasylczyk, P.; Parmeggiani, C.; Martella, D.; Burresi, M.; Wiersma, D. . Light-fueled microscopic walkers . Adv. Mater. , 2015 . 27 3883 - 3887 . DOI: 10.1002/adma.201501446 http://doi.org/10.1002/adma.201501446 .

Ichimura, K.; Oh, S.; Nakagawa, M. . Light-driven motion of liquids on a photoresponsive surface . Science , 2000 . 288 1624 - 1626 . DOI: 10.1126/science.288.5471.1624 http://doi.org/10.1126/science.288.5471.1624 .

Yu, H.; Ikeda, T. . Photocontrollable liquid-crystalline actuators . Adv. Mater. , 2011 . 23 2149 - 2180 . DOI: 10.1002/adma.201100131 http://doi.org/10.1002/adma.201100131 .

Qin, C.; Feng, Y.; Luo, W.; Cao, C.; Hu, W.; Feng, W. . A supramolecular assembly of cross-linked azobenzene/polymers for a high-performance light-driven actuator . J. Mater. Chem. A , 2015 . 3 16453 - 16460 . DOI: 10.1039/C5TA01543J http://doi.org/10.1039/C5TA01543J .

Ikejiri, S.; Takashima, Y.; Osaki, M.; Yamaguchi, H.; Harada, A. . Solvent-free photoresponsive artificial muscles rapidly driven by molecular machines . J. Am. Chem. Soc. , 2018 . 140 17308 - 17315 . DOI: 10.1021/jacs.8b11351 http://doi.org/10.1021/jacs.8b11351 .

Takashima, Y.; Hayashi, Y.; Osaki, M.; Kaneko, F.; Yamaguchi, H.; Harada, A. . A photoresponsive polymeric actuator topologically cross-linked by movable units based on a [2]rotaxane . Macromolecules , 2018 . 51 4688 - 4693 . DOI: 10.1021/acs.macromol.8b00939 http://doi.org/10.1021/acs.macromol.8b00939 .

Mauro, M. . Gel-based soft actuators driven by light . J. Mater. Chem. B , 2019 . 7 4234 - 4242 . DOI: 10.1039/C8TB01893F http://doi.org/10.1039/C8TB01893F .

Iwaso, K.; Takashima, Y.; Harada, A. . Fast response dry-type artificial molecular muscles with [c2]daisy chains . Nat. Chem. , 2016 . 8 625 - 632 . DOI: 10.1038/nchem.2513 http://doi.org/10.1038/nchem.2513 .

Iamsaard, S.; Abhoff, S.; Matt, B.; Kudernac, T.; Cornelissen, J.; Fletcher, S.; Katsonis, N. . Conversion of light into macroscopic helical motion . Nat. Chem. , 2014 . 6 229 - 235 . DOI: 10.1038/nchem.1859 http://doi.org/10.1038/nchem.1859 .

Qin, C. Q.; Feng, Y. Y.; Luo, W.; Cao, C.; Hu, W. P.; Feng, W. . A supramolecular assembly of cross-linked azobenzene/polymers for a high-performance light-driven actuator . J. Mater. Chem. A , 2015 . 3 16453 - 16460 . DOI: 10.1039/C5TA01543J http://doi.org/10.1039/C5TA01543J .

Ma, S. D.; Li, X.; Huang, S.; Hu, J.; Yu, H. F. . A Light-activated polymer composite enables on-demand photocontrol of biomimetic swimming towards transportation at liquid/air interface . Angew. Chem. Int. Ed. , 2019 . 58 2655 - 2659 . DOI: 10.1002/anie.201811808 http://doi.org/10.1002/anie.201811808 .

Cheng, Z. X.; Wang, T. J.; Li, X.; Zhang, Y. H.; Yu, H. F. . NIR-Vis-UV light-responsive actuator films of polymer-dispersed liquid crystal/graphene oxide nanocomposites . ACS Appl. Mater. Interfaces , 2015 . 7 27494 - 27501 . DOI: 10.1021/acsami.5b09676 http://doi.org/10.1021/acsami.5b09676 .

Lv, J. A.; Wang, W.; Wu, W.; Yu, Y. L. . A reactive azobenzene liquid-crystalline block copolymer as a promising material for practical application of light-driven soft actuators . J. Mater. Chem. C , 2015 . 3 6621 - 6626 . DOI: 10.1039/C5TC00595G http://doi.org/10.1039/C5TC00595G .

Pang, X. L.; Xu, B.; Qing, X.; Wei, J.; Yu, Y. L. . Photo-induced bending behavior of post-crosslinked liquid crystalline polymer/polyurethane blend films . Macromol. Rapid Commun. , 2018 . 39 1700237 DOI: 10.1002/marc.201700237 http://doi.org/10.1002/marc.201700237 .

Petr, M.; Katzman, B.; DiNatale, W.; Hammond, P. . Synthesis of a new, low- T g siloxane thermoplastic elastomer with a functionalizable backbone and its use as a rapid room temperature photoactuator . Macromolecules , 2013 . 46 2823 - 2832 . DOI: 10.1021/ma400031z http://doi.org/10.1021/ma400031z .

Lahikainen, M.; Zeng, H.; Priimagi, A. . Reconfigurable photoactuator through synergistic use of photochemical and photothermal effects . Nat. Commun. , 2018 . 9 1 DOI: 10.1038/s41467-017-02088-w http://doi.org/10.1038/s41467-017-02088-w .

Lu, X. L.; Zhang, H.; Fei, G. X.; Yu, B.; Tong, X.; Xia, H. S.; Zhao, Y. . Liquid-crystalline dynamic networks doped with gold nanorods showing enhanced photocontrol of actuation . Adv. Mater. , 2018 . 30 1706597 DOI: 10.1002/adma.201706597 http://doi.org/10.1002/adma.201706597 .

Xiao, R. Q.; Zhou, L. P.; Dong, Z. Y.; Gao, Y. Z.; Liu, J. Q. . A photo-responsive catalytic vesicle with GPx activity . Chinese J. Chem. , 2014 . 32 37 - 43 . DOI: 10.1002/cjoc.201300695 http://doi.org/10.1002/cjoc.201300695 .

Babu, R. R.; Kumaresan, S.; Vijayan, N.; Gunasekaran, M.; Gopalakrishnan, R.; Kannan, P.; Ramasamy, P. . Growth of 4,4 ' -dihydroxyazobenzene (DHAB) and its characterization . J. Cryst. Growth , 2003 . 256 387 - 392 . DOI: 10.1016/S0022-0248(03)01369-1 http://doi.org/10.1016/S0022-0248(03)01369-1 .

Views

155

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Long Alkyl Tails Amplify Photoswitchable Glass Transition Temperatures of Azopolymers for Nanoimprint Lithography

Engineering Light-responsive Azo-polyurethane Actuators: Integrated Self-healing and Reshaping via Synergistic Disulfide-hydrogen Bonding

Non-covalently Functionalized Carbon Nanotube by Hyaluronic Acid Based Azo Polymer for Photothermal Elimination of Tumor Cells

Polymer Materials Synthesized in Living Cells for Regulating Biological Functions

Sliding Dynamics of Ring Chain on a Rod-Coil Block Copolymer in Rotaxane

Related Author

Zhu-Lu Xie

Fu-Wei Kong

Jia-Hui Chen

Jie Yan

Bo-Ting Wang

Tian-Ren Zhao

Shuo-Feng Liang

Si Wu

Related Institution

Hefei National Research Center for Physical Sciences at the Microscale, Anhui Key Laboratory of Optoelectronic Science and Technology, Department of Polymer Science and Engineering, University of Science and Technology of China

School of Materials Science and Engineering, Tianjin University

Wanhua Chemical Group Co., Ltd.

Zonkex Engineering Consulting (Beijing) Co., Ltd.

School of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Extreme Environment-tolerant Specialty Chemicals, University of Jinan

⁰