Hyperbranched Azopolymer with Quadruple Responsibility

Chen Tian; Ke-Cong Zhou; Yu-Fei Lu; Jin-Jie Li; Yuan Yao; Xin-Feng Tao; Qi-Xin Zhuang; Yu-Feng Xie; Shao-Liang Lin

doi:10.1007/s10118-021-2576-1

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Hyperbranched Azopolymer with Quadruple Responsibility

ARTICLE | Updated：2021-05-25

- Hyperbranched Azopolymer with Quadruple Responsibility
- Hyperbranched Azopolymer with Quadruple Responsibility
- Chinese Journal of Polymer Science 2021年39卷第9期页码：1169-1176
- Affiliations：
  
  a.Shanghai Key Laboratory of Advanced Polymeric Materials, Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
  b.Department of Periodontology, Shanghai Ninth People's Hospital, College of Stomatology, Shanghai Key Laboratory of Stomatology & Shanghai Research Institute of Stomatology, Shanghai Jiao Tong University, Shanghai 200011, China
- Author bio：
  
  yaoyuan@ecust.edu.cn (Y.Y.)
  xieyf1657@sh9hospital.org.cn (Y.F.X)
  slin@ecust.edu.cn (S.L.L.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 52073092, 52073094 and 51873061) and the Projects of Shanghai Municipality (Nos. 18JC1410802 and 17JC400700).
- DOI：10.1007/s10118-021-2576-1
  中图分类号：
- 收稿：2021-01-22，
  
  修回：2021-3-1，
  
  录用：2021-3-8，
  
  网络首发：2021-05-25，
  
  纸质出版：2021-07-18
- Accepted：
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Tian, C.; Zhou, K. C.; Lu, Y. F.; Li, J. J.; Yao, Y.; Tao, X. F.; Zhuang, Q. X.; Xie, Y. F.; Lin, S. L. Hyperbranched azopolymer with quadruple responsibility. Chinese J. Polym. Sci. 2021, 39, 1169–1176

Chen Tian, Ke-Cong Zhou, Yu-Fei Lu, et al. Hyperbranched Azopolymer with Quadruple Responsibility[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1169-1176.
Tian, C.; Zhou, K. C.; Lu, Y. F.; Li, J. J.; Yao, Y.; Tao, X. F.; Zhuang, Q. X.; Xie, Y. F.; Lin, S. L. Hyperbranched azopolymer with quadruple responsibility. Chinese J. Polym. Sci. 2021, 39, 1169–1176 DOI： 10.1007/s10118-021-2576-1.

Chen Tian, Ke-Cong Zhou, Yu-Fei Lu, et al. Hyperbranched Azopolymer with Quadruple Responsibility[J]. Chinese Journal of Polymer Science, 2021, 39(9): 1169-1176. DOI： 10.1007/s10118-021-2576-1.

摘要

Abstract

Simply constructing multiple responsive polymers with obvious shape and dimension variations on their assemblies upon different stimuli is still rarely reported. In this study

we report a hyperbranched polymer named HPAzoBAHB-

star

-PEG

with quadruple-response to light

temperature

pH and oxidation stimuli. The polymer contains azobenzene chromophore

sulfide

amide and amine groups in its hydrophobic hyperbranched core

and the core is capped with hydrophilic polyethylene glycol (PEG

) arms. HPAzoBAHB-

star

-PEG

could assemble into unusual leaf-like lamellar micelles at 25 °C under the guidance of orderly arranged

-aggregate of azobenzene moieties. These leaf-like lamellar micelles can transform into vesicles upon UV irradiation and lower temperature

or convert to smaller spherical micelles in acidic or oxidative environments

respectively

with the destroy of ordered azobenzene arrangements. This quadruple-responsive hyperbranched polymer is suitable to construct multiple stimuli-responsive micro/nanostructures

or accurate delivery and release following subtle stimuli sequences.

关键词

Keywords

references

Dai, S.; Ravi, P.; Tam, K. C. . pH-Responsive polymers: synthesis, properties and applications . Soft Matter , 2008 . 4 435 - 439 . DOI: 10.1039/b714741d http://doi.org/10.1039/b714741d .

Roy, D.; Brooks, W. L.; Sumerlin, B. S. . New directions in thermoresponsive polymers . Chem. Soc. Rev. , 2013 . 42 7214 - 7243 . DOI: 10.1039/c3cs35499g http://doi.org/10.1039/c3cs35499g .

Ren, H.; Chen, D.; Shi Y.; Yu, H. F.; Fu, Z. F.; Yang, W. T. . Charged end-group terminated poly( N -isopropylacrylamide)- b -poly(carboxylic azo) with unusual thermoresponsive behaviors . Macromolecules , 2018 . 51 3290 - 3298 . DOI: 10.1021/acs.macromol.7b02640 http://doi.org/10.1021/acs.macromol.7b02640 .

Lv, J. A.; Liu, Y.; Wei, J.; Chen, E.; Qin, L.; Yu, Y. . Photocontrol of fluid slugs in liquid crystal polymer microactuators . Nature , 2016 . 537 179 - 184 . DOI: 10.1038/nature19344 http://doi.org/10.1038/nature19344 .

Kramer, J. R.; Deming, T. J. . Glycopolypeptides with a redox-triggered helix-to-coil transition . J. Am. Chem. Soc. , 2012 . 134 4112 - 4115 . DOI: 10.1021/ja3007484 http://doi.org/10.1021/ja3007484 .

Rideau, E.; Dimova, R.; Schwille, P.; Wurm, F. R.; Landfester, K. . Liposomes and polymersomes: a comparative review towards cell mimicking . Chem. Soc. Rev. , 2018 . 47 8572 - 8610 . DOI: 10.1039/C8CS00162F http://doi.org/10.1039/C8CS00162F .

Chen, Y.; Wang, Z.; He, Y.; Yoon, Y. J.; Jung, J.; Zhang, G.; Lin, Z. . Light-enabled reversible self-assembly and tunable optical properties of stable hairy nanoparticles . Proc. Natl. Acad. Sci. USA , 2018 . 115 E1391 - E1400 . DOI: 10.1073/pnas.1714748115 http://doi.org/10.1073/pnas.1714748115 .

Ramasamy, T.; Ruttala, H. B.; Gupta, B.; Poudel, B. K.; Choi, H. G.; Yong, C. S.; Kim, J. O. . Smart chemistry-based nanosized drug delivery systems for systemic applications: A comprehensive review . J. Control. Release , 2017 . 258 226 - 253 . DOI: 10.1016/j.jconrel.2017.04.043 http://doi.org/10.1016/j.jconrel.2017.04.043 .

Bajpai, A. K.; Shukla, S. K.; Bhanu, S.; Kankane, S. . Responsive polymers in controlled drug delivery . Prog. Polym. Sci. , 2008 . 33 1088 - 1118 . DOI: 10.1016/j.progpolymsci.2008.07.005 http://doi.org/10.1016/j.progpolymsci.2008.07.005 .

Zheng, X. X.; Bian, Q.; Ye, C. X.; Wang, G. J. . Visible light-, pH-, and cyclodextrin-responsive azobenzene functionalized polymeric nanoparticles . Dyes Pigments , 2019 . 162 599 - 605 . DOI: 10.1016/j.dyepig.2018.10.063 http://doi.org/10.1016/j.dyepig.2018.10.063 .

Li, Q. W.; Cao, Z. Q.; Wang, G. J. . Diazonaphthoquinone-based amphiphilic polymer assemblies for NIR/UV light- and pH-responsive controlled release . Polym. Chem. , 2018 . 9 463 - 471 . DOI: 10.1039/C7PY01822C http://doi.org/10.1039/C7PY01822C .

Duan, J. J.; Zhang, L. N. . Robust and smart hydrogels based on natural polymers . Chinese J. Polym. Sci. , 2017 . 35 1165 - 1180 . DOI: 10.1007/s10118-017-1983-9 http://doi.org/10.1007/s10118-017-1983-9 .

Hu, J.; Liu, S. . Responsive polymers for detection and sensing applications: current status and future developments . Macromolecules , 2010 . 43 8315 - 8330 . DOI: 10.1021/ma1005815 http://doi.org/10.1021/ma1005815 .

Wong, R. C. H.; Lo, P. C.; Ng, D. K. P. . Stimuli responsive phthalocyanine-based fluorescent probes and photosensitizers . Coord. Chem. Rev. , 2019 . 379 30 - 46 . DOI: 10.1016/j.ccr.2017.10.006 http://doi.org/10.1016/j.ccr.2017.10.006 .

Wei, M.; Gao, Y.; Li, X.; Serpe, M. J. . Stimuli-responsive polymers and their applications . Polym. Chem. , 2017 . 8 127 - 143 . DOI: 10.1039/C6PY01585A http://doi.org/10.1039/C6PY01585A .

Ren, H.; Chen, D.; Shi Y.; Yu, H. F.; Fu, Z. F. . A carboxylic azo monomer and its homopolymer: synthesis, self-organization and fluorescence behaviour in solution . Polym. Chem. , 2015 . 6 270 - 277 . DOI: 10.1039/C4PY01062K http://doi.org/10.1039/C4PY01062K .

Chen, S.; Bian, Q.; Wang, P. J.; Zheng, X. W.; Lv, L.; Dang, Z. M.; Wang, G. J. . Photo, pH and redox multi-responsive nanogels for drug delivery and fluorescence cell imaging . Polym. Chem. , 2017 . 8 6150 - 6157 . DOI: 10.1039/C7PY01424D http://doi.org/10.1039/C7PY01424D .

Ding, L.; Zhang, L. Y.; Han, H. J.; Huang, W.; Song, C. M.; Xie, M. R.; Zhang, Y. Q. . Hyperbranched Azo-polymers synthesized by acyclic diene metathesis polymerization of an AB(2) monomer . Macromolecules , 2009 . 42 5036 - 5042 . DOI: 10.1021/ma900412b http://doi.org/10.1021/ma900412b .

Liu, H. J.; Dong, R. H.; Chen, Y. . Preparation and characterization of thermoresponsive hyperbranched polyethylenimine with plenty of reactive primary amine groups . Chinese J. Polym. Sci. , 2014 . 32 961 - 968 . DOI: 10.1007/s10118-014-1471-4 http://doi.org/10.1007/s10118-014-1471-4 .

Wang, R. B.; Yuan, W. Z.; Zhu, X. Y. . Aggregation-induced emission of non-conjugated poly(amido amine)s: discovering, luminescent mechanism understanding and bioapplication . Chinese J. Polym. Sci. , 2015 . 33 680 - 687 . DOI: 10.1007/s10118-015-1635-x http://doi.org/10.1007/s10118-015-1635-x .

Shi, X.; Zhao, Y.; Gao, H.; Zhang, L.; Zhu, F.; Wu, Q. . Synthesis of hyperbranched polyethylene amphiphiles by chain walking polymerization in tandem with RAFT polymerization and supramolecular self-assembly vesicles . Macromol. Rapid Commun. , 2012 . 33 374 - 379 . DOI: 10.1002/marc.201100825 http://doi.org/10.1002/marc.201100825 .

Heo, M. S.; Seo, E. J.; John, J. V.; Jang, I. H.; Kim, J. H.; Kim, I. . Synthesis of hyperbranched polyglycidol- b -poly( N -isopropylacrylamide) using nitroxide-mediated polymerization for thermo-sensitive drug delivery system . J. Control. Release , 2015 . 213 E80 .

Fan, W. W.; Fan, X. D.; Tian, W.; Zhang, X.; Wang, G.; Zhang, W. B.; Bai, Y.; Zhu, X. Z. . Phase transition dynamics and mechanism for backbone-thermoresponsive hyperbranched polyethers . Polym. Chem. , 2014 . 5 4022 - 4031 . DOI: 10.1039/c4py00155a http://doi.org/10.1039/c4py00155a .

Zhang, Y. W.; Huang, W.; Zhou, Y. F.; Yan, D. Y. . A physical gel made from hyperbranched polymer gelator . Chem. Commun. , 2007 . 2587 - 2589 . .

Zhang, J.; Liu, H. J.; Yuan, Y.; Jiang, S.; Yao, Y.; Chen, Y. . Thermo-, pH-, and light-responsive supramolecular complexes based on a thermoresponsive hyperbranched polymer . ACS Macro Lett. , 2012 . 2 67 - 71 . .

Sun, L.; Gao, F.; Shen, D.; Liu, Z.; Yao, Y.; Lin, S. . Rationally designed hyperbranched azopolymer with temperature, photo and pH responsive behavior . Polym. Chem. , 2018 . 9 2977 - 2983 . DOI: 10.1039/C8PY00472B http://doi.org/10.1039/C8PY00472B .

Fu, S.; Zhao, Y. . Orientation of azobenzene mesogens in side-chain liquid crystalline polymers: interplay between effects of mechanical stretching, photoisomerization and thermal annealing . Macromolecules , 2015 . 48 5088 - 5098 . DOI: 10.1021/acs.macromol.5b01311 http://doi.org/10.1021/acs.macromol.5b01311 .

Seki, T. . New strategies and implications for the photoalignment of liquid crystalline polymers . Polym. J. , 2014 . 46 751 - 768 . DOI: 10.1038/pj.2014.68 http://doi.org/10.1038/pj.2014.68 .

Seki, T.; Nagano, S. . Light-directed dynamic structure formation and alignment in photoresponsive thin films . Chem. Lett. , 2008 . 37 484 - 489 . DOI: 10.1246/cl.2008.484 http://doi.org/10.1246/cl.2008.484 .

Han, D.; Tong, X.; Zhao, Y.; Zhao, Y. . Block copolymers comprising pi-conjugated and liquid crystalline subunits: induction of macroscopic nanodomain orientation . Angew. Chem. Int. Ed. , 2010 . 49 9162 - 9165 . DOI: 10.1002/anie.201004445 http://doi.org/10.1002/anie.201004445 .

Yu, H.; Kobayashi, T. . Photoresponsive block copolymers containing azobenzenes and other chromophores . Molecules , 2010 . 15 570 - 603 . DOI: 10.3390/molecules15010570 http://doi.org/10.3390/molecules15010570 .

Yu, H. . Photoresponsive liquid crystalline block copolymers: from photonics to nanotechnology . Prog. Polym. Sci. , 2014 . 39 781 - 815 . DOI: 10.1016/j.progpolymsci.2013.08.005 http://doi.org/10.1016/j.progpolymsci.2013.08.005 .

del, Barrio J.; Oriol, L.; Sanchez, C.; Serrano, J. L.; Di, Cicco A.; Keller, P.; Li, M. H. . Self-assembly of linear-dendritic diblock copolymers: from nanofibers to polymersomes . J. Am. Chem. Soc. , 2010 . 132 3762 - 3769 . DOI: 10.1021/ja9083946 http://doi.org/10.1021/ja9083946 .

Deng, W.; Albouy, P. A.; Lacaze, E.; Keller, P.; Wang, X. G.; Li, M. H. . Azobenzene-containing liquid crystal triblock copolymers: synthesis, characterization, and self-assembly behavior . Macromolecules , 2008 . 41 2459 - 2466 . DOI: 10.1021/ma702590j http://doi.org/10.1021/ma702590j .

Wu, S.; Wang, L.; Kroeger, A.; Wu, Y. P.; Zhang, Q. J.; Bubeck, C. . Block copolymers of PS- b -PEO co-assembled with azobenzene-containing homopolymers and their photoresponsive properties . Soft Matter , 2011 . 7 11535 - 11545 . DOI: 10.1039/c1sm06316b http://doi.org/10.1039/c1sm06316b .

Zhang, W. Q.; Xie, J. D.; Yang, Z.; Shi, W. F. . Aggregation behaviors and photoresponsive properties of azobenzene constructed phosphate dendrimers . Polymer , 2007 . 48 4466 - 4481 . DOI: 10.1016/j.polymer.2007.05.056 http://doi.org/10.1016/j.polymer.2007.05.056 .

Li, Y. B.; Deng, Y. H.; Tong, X. L.; Wang, X. G. . Formation of photoresponsive uniform colloidal spheres from an amphiphilic azobenzene-containing random copolymer . Macromolecules , 2006 . 39 1108 - 1115 . DOI: 10.1021/ma052272y http://doi.org/10.1021/ma052272y .

Wang, W.; Yao, Y.; Luo, T.; Chen, L.; Lin, J.; Li, L.; Lin, S. . Deterministic reshaping of breath figure arrays by directional photomanipulation . ACS Appl. Mater. Interfaces , 2017 . 9 4223 - 4230 . DOI: 10.1021/acsami.6b14024 http://doi.org/10.1021/acsami.6b14024 .

Kong, X.; Wang, X.; Luo, T.; Yao, Y.; Li, L.; Lin, S. . Photomanipulated architecture and patterning of azopolymer array . ACS Appl. Mater. Interfaces , 2017 . 9 19345 - 19353 . DOI: 10.1021/acsami.7b04273 http://doi.org/10.1021/acsami.7b04273 .

Lee, S.; Kang, H. S.; Park, J. K. . Directional photofluidization lithography: micro/nanostructural evolution by photofluidic motions of azobenzene materials . Adv. Mater. , 2012 . 24 2069 - 2103 . DOI: 10.1002/adma.201104826 http://doi.org/10.1002/adma.201104826 .

Lee, S. A.; Kang, H. S.; Park, J. K.; Lee, S. . Vertically oriented, three-dimensionally tapered deep-subwavelength metallic nanohole arrays developed by photofluidization lithography . Adv. Mater. , 2014 . 26 7521 - 7528 . DOI: 10.1002/adma.201403098 http://doi.org/10.1002/adma.201403098 .

Wang, W.; Du, C.; Wang, X.; He, X.; Lin, J.; Li, L.; Lin, S. . Directional photomanipulation of breath figure arrays . Angew. Chem. Int. Ed. , 2014 . 53 12116 - 12119 . DOI: 10.1002/anie.201407230 http://doi.org/10.1002/anie.201407230 .

Gao, F.; Yao, Y.; Wang, W.; Wang, X.; Li, L.; Zhuang, Q.; Lin, S. . Light-driven transformation of bio-inspired superhydrophobic structure via reconfigurable pazoma microarrays: from lotus leaf to rice leaf . Macromolecules , 2018 . 51 2742 - 2749 . DOI: 10.1021/acs.macromol.8b00059 http://doi.org/10.1021/acs.macromol.8b00059 .

Wang, W.; Shen, D.; Li, X.; Yao, Y.; Lin, J.; Wang, A.; Yu, J.; Wang, Z. L.; Hong, S. W.; Lin, Z.; Lin, S. . Light-driven shape-memory porous films with precisely controlled dimensions . Angew. Chem. Int. Ed. , 2018 . 57 2139 - 2143 . DOI: 10.1002/anie.201712100 http://doi.org/10.1002/anie.201712100 .

Li, X.; Ma, S.; Hu, J.; Ni, Y.; Lin, Z.; Yu, H. . Photo-activated bimorph composites of Kapton and liquid-crystalline polymer towards biomimetic circadian rhythms of Albizia julibrissin leaves . J. Mater. Chem. C , 2019 . 7 622 - 629 . DOI: 10.1039/C8TC05186K http://doi.org/10.1039/C8TC05186K .

Cheng, Z.; Ma, S.; Zhang, Y.; Huang, S.; Chen, Y.; Yu, H. . Photomechanical motion of liquid-crystalline fibers bending away from a light source . Macromolecules , 2017 . 50 8317 - 8324 . DOI: 10.1021/acs.macromol.7b01741 http://doi.org/10.1021/acs.macromol.7b01741 .

Fu, X.; Ma, Y.; Shen, Y.; Fu, W.; Li, Z. . Oxidation-responsive OEGylated poly-L-cysteine and solution properties studies . Biomacromolecules , 2014 . 15 1055 - 1061 . DOI: 10.1021/bm5000554 http://doi.org/10.1021/bm5000554 .

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