Design of Poly(l-lactide)-Poly(ethylene glycol) Copolymer with Light-Induced Shape-Memory Effect Triggered by Pendant Anthracene Groups

ACS Applied Materials and Interfaces

Volumn 8, Issue 14, 2016, Pages 9431-9439

  Xie, Hui ^a   He, Man Jie ^a   Deng, Xiao Ying ^a   Du, Lan ^a   Fan, Cheng Jie ^a   Yang, Ke Ke ^a   Wang, Yu Zhong ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

anthracene; light induced; poly(ethylene glycol); poly(l lactide); shape memory

Indexed keywords

ANTHRACENE; CYCLOADDITION; DIFFERENTIAL SCANNING CALORIMETRY; ETHYLENE GLYCOL; POLYETHYLENE OXIDES; POLYOLS; SHAPE MEMORY EFFECT; TENSILE TESTING;

CYCLOADDITION REACTION; LIGHT-INDUCED; PHOTO-RESPONSIVE; POLY (L-LACTIDE); SHAPE MEMORY; SHAPE-MEMORY MATERIALS; STATIC TENSILE TESTS; SYNTHESIS STRATEGY;

POLYETHYLENE GLYCOLS;

EID: 84964868605     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.6b00704     Document Type: Article

References (44)

1. Lendlein, A.; Jiang, H.; Junger, O.; Langer, R. Light-induced shape-memory polymers Nature 2005, 434, 879-882 10.1038/nature03496
2. Huang, W. M.; Ding, Z.; Wang, C. C.; Wei, J.; Zhao, Y.; Purnawali, H. Shape memory materials Mater. Today 2010, 13, 54-61 10.1016/S1369-7021(10)70128-0
3. Behl, M.; Razzaq, M. Y.; Lendlein, A. Multifunctional shape-memory polymers Adv. Mater. 2010, 22, 3388-410 10.1002/adma.200904447
4. Wen, Z.; Zhang, T.; Hui, Y.; Wang, W.; Yang, K.; Zhou, Q.; Wang, Y. Elaborate fabrication of well-defined side-chain liquid crystalline polyurethane networks with triple-shape memory capacity J. Mater. Chem. A 2015, 3, 13435-13444 10.1039/C5TA02537K
5. Huang, W. M.; Yang, B.; Zhao, Y.; Ding, Z. Thermo-moisture responsive polyurethane shape-memory polymer and composites: a review J. Mater. Chem. 2010, 20, 3367-3381 10.1039/b922943d
6. Zhang, J.; Wu, G.; Huang, C.; Niu, Y.; Chen, C.; Chen, Z.; Yang, K.; Wang, Y. Unique Multifunctional Thermally-Induced Shape Memory PPDO-PTMEG Multiblock Copolymers Based on the Synergistic Effect of Two Segments J. Phys. Chem. C 2012, 116, 5835-5845 10.1021/jp211953q
7. Lendlein, A.; Langer, R. Biodegradable, elastic shape-memory polymers for potential biomedical applications Science 2002, 296, 1673-1676 10.1126/science.1066102
8. Kohl, M.; Brugger, D.; Ohtsuka, M.; Takagi, T. A novel actuation mechanism on the basis of ferromagnetic SMA thin films Sens. Actuators, A 2004, 114, 445-450 10.1016/j.sna.2003.11.006
9. Kunzelman, J.; Chung, T.; Mather, P. T.; Weder, C. Shape memory polymers with built-in threshold temperature sensors J. Mater. Chem. 2008, 18, 1082-1086 10.1039/b718445j
10. Niu, Y.; Zhang, P.; Zhang, J.; Xiao, L.; Yang, K.; Wang, Y. Poly(p-dioxanone)-poly(ethylene glycol) network: synthesis, characterization, and its shape memory effect Polym. Chem. 2012, 3, 2508-2516 10.1039/c2py20311a
11. Zhang, J.; Niu, Y.; Huang, C.; Xiao, L.; Chen, Z.; Yang, K.; Wang, Y. Self-healable and recyclable triple-shape PPDO-PTMEG co-network constructed through thermoreversible Diels-Alder reaction Polym. Chem. 2012, 3, 1390-1393 10.1039/c2py20028g
12. Xiao, L. P.; Wei, M.; Zhan, M. Q.; Zhang, J. J.; Xie, H.; Deng, X. Y.; Yang, K. K.; Wang, Y. Z. Novel triple-shape PCU/PPDO interpenetrating polymer networks constructed by self-complementary quadruple hydrogen bonding and covalent bonding Polym. Chem. 2014, 5, 2231-2241 10.1039/c3py01476b
13. Wei, M.; Zhan, M.; Yu, D.; Xie, H.; He, M.; Yang, K.; Wang, Y. Novel poly(tetramethylene ether)glycol and poly(epsilon-caprolactone) based dynamic network via quadruple hydrogen bonding with triple-shape effect and self-healing capacity ACS Appl. Mater. Interfaces 2015, 7, 2585-2596 10.1021/am507575z
14. Raquez, J. M.; Vanderstappen, S.; Meyer, F.; Verge, P.; Alexandre, M.; Thomassin, J. M.; Jerome, C.; Dubois, P. Design of cross-linked semicrystalline poly(epsilon-caprolactone)-based networks with one-way and two-way shape-memory properties through Diels-Alder reactions Chem.-Eur. J. 2011, 17, 10135-10143 10.1002/chem.201100496
15. Zhan, M. Q.; Yang, K. K.; Wang, Y. Z. Shape-memory poly(p-dioxanone)-poly(ϵ-caprolactone)/sepiolite nanocomposites with enhanced recovery stress Chin. Chem. Lett. 2015, 26, 1221-1224 10.1016/j.cclet.2015.07.019
16. Zhang, T.; Wen, Z.; Hui, Y.; Yang, M.; Yang, K.; Zhou, Q.; Wang, Y. Facile fabrication of a well-defined poly(p-dioxanone) dynamic network from metallosupramolecular interactions to obtain an excellent shape-memory effect Polym. Chem. 2015, 6, 4177-4184 10.1039/C5PY00507H
17. Wu, L. B.; Jin, C. J.; Sun, X. Y. Synthesis, Properties, and Light-Induced Shape Memory Effect of Multiblock Polyesterurethanes Containing Biodegradable Segments and Pendant Cinnamamide Groups Biomacromolecules 2011, 12, 235-241 10.1021/bm1012162
18. Koerner, H.; Price, G.; Pearce, N. A.; Alexander, M.; Vaia, R. A. Remotely actuated polymer nanocomposites - stress-recovery of carbon-nanotube-filled thermoplastic elastomers Nat. Mater. 2004, 3, 115-120 10.1038/nmat1059
19. Kumpfer, J. R.; Rowan, S. J. Thermo-, photo-, and chemo-responsive shape-memory properties from photo-cross-linked metallo-supramolecular polymers J. Am. Chem. Soc. 2011, 133, 12866-12874 10.1021/ja205332w
20. Leng, J.; Wu, X.; Liu, Y. Infrared light-active shape memory polymer filled with nanocarbon particles J. Appl. Polym. Sci. 2009, 114, 2455-2460 10.1002/app.30724
21. Hribar, K. C.; Metter, R. B.; Ifkovits, J. L.; Troxler, T.; Burdick, J. A. Light-induced temperature transitions in biodegradable polymer and nanorod composites Small 2009, 5, 1830-1834 10.1002/smll.200900395
22. Zhang, H.; Xia, H.; Zhao, Y. Optically triggered and spatially controllable shape-memory polymer-gold nanoparticle composite materials J. Mater. Chem. 2012, 22, 845-849 10.1039/C1JM14615G
23. Zhang, H.; Zhao, Y. Polymers with dual light-triggered functions of shape memory and healing using gold nanoparticles ACS Appl. Mater. Interfaces 2013, 5, 13069-13075 10.1021/am404087q
24. Gu, S.; Yan, B.; Liu, L.; Ren, J. Carbon nanotube-polyurethane shape memory nanocomposites with low trigger temperature Eur. Polym. J. 2013, 49, 3867-3877 10.1016/j.eurpolymj.2013.10.007
25. Lu, H.; Yao, Y.; Huang, W. M.; Leng, J.; Hui, D. Significantly improving infrared light-induced shape recovery behavior of shape memory polymeric nanocomposite via a synergistic effect of carbon nanotube and boron nitride Composites, Part B 2014, 62, 256-261 10.1016/j.compositesb.2014.03.007
26. Ishii, S.; Uto, K.; Niiyama, E.; Ebara, M.; Nagao, T. Hybridizing Poly(ϵ-caprolactone) and Plasmonic Titanium Nitride Nanoparticles for Broadband Photoresponsive Shape Memory Films ACS Appl. Mater. Interfaces 2016, 8, 5634-5640 10.1021/acsami.5b12658
27. Jiang, H. Y.; Kelch, S.; Lendlein, A. Polymers Move in Response to Light Adv. Mater. 2006, 18, 1471-1475 10.1002/adma.200502266
28. Pilate, F.; Mincheva, R.; De Winter, J.; Gerbaux, P.; Wu, L. B.; Todd, R.; Raquez, J. M.; Dubois, P. Design of Multistimuli-Responsive Shape-Memory Polymer Materials by Reactive Extrusion Chem. Mater. 2014, 26, 5860-5867 10.1021/cm5020543
29. Rochette, J. M.; Ashby, V. S. Photoresponsive Polyesters for Tailorable Shape Memory Biomaterials Macromolecules 2013, 46, 2134-2140 10.1021/ma302354a
30. Bartz, T.; Klapper, M.; Müllen, K.; Schulz, R. C. A novel synthesis of polymers with anthracene and dihydroanthracene subunits in the main chain Polym. Int. 1993, 31, 153-162 10.1002/pi.4990310206
31. Coursan, M.; Desvergne, J. P.; Deffieux, A. Reversible photodimerisation of ω-anthrylpolystyrenes Macromol. Chem. Phys. 1996, 197, 1599-1608 10.1002/macp.1996.021970502
32. Goldbach, J. T.; Russell, T. P.; Penelle, J. Synthesis and Thin Film Characterization of Poly(styrene-block-methyl Macromolecules 2002, 35, 4271-4276 10.1021/ma011940m
33. Paul, S.; Stein, S.; Knoll, W.; Müllen, K. Photobleaching of oligoanthrylenes in the film state Acta Polym. 1996, 47, 92-98 10.1002/actp.1996.010470205
34. Connal, L. A.; Vestberg, R.; Hawker, C. J.; Qiao, G. G. Fabrication of Reversibly Crosslinkable, 3-Dimensionally Conformal Polymeric Microstructures Adv. Funct. Mater. 2008, 18, 3315-3322 10.1002/adfm.200800333
35. Wojtecki, R. J.; Meador, M. A.; Rowan, S. J. Using the dynamic bond to access macroscopically responsive structurally dynamic polymers Nat. Mater. 2011, 10, 14-27 10.1038/nmat2891
36. Wang, H.; Liu, F.; Helgeson, R. C.; Houk, K. N. Reversible Photochemically Gated Transformation of a Hemicarcerand to a Carcerand Angew. Chem., Int. Ed. 2013, 52, 655-659 10.1002/anie.201205376
37. Xu, J. F.; Chen, Y. Z.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Dynamic Covalent Bond Based on Reversible Photo [4 + 4] Cycloaddition of Anthracene for Construction of Double-Dynamic Polymers Org. Lett. 2013, 15, 6148-6151 10.1021/ol403015s
38. López-Vilanova, L.; Martínez, I.; Corrales, T.; Catalina, F. Photochemical crosslinking of poly-(ethylene-butyl-acrylate) copolymers functionalized with anthracene moieties by reactive extrusion Eur. Polym. J. 2014, 56, 69-76 10.1016/j.eurpolymj.2014.04.005
39. Trinh, X. A.; Fukuda, J.; Adachi, Y.; Nakanishi, H.; Norisuye, T.; Tran-Cong-Miyata, Q. Effects of Elastic Deformation on Phase Separation of a Polymer Macromolecules 2007, 40, 5566-5574 10.1021/ma0705220
40. Habault, D.; Zhang, H.; Zhao, Y. Light-triggered self-healing and shape-memory polymers Chem. Soc. Rev. 2013, 42, 7244-7256 10.1039/c3cs35489j
41. Zheng, Y. J.; Micic, M.; Mello, S. V.; Mabrouki, M.; Andreopoulos, F. M.; Konka, V.; Pham, S. M.; Leblanc, R. M. PEG-Based Hydrogel Synthesis via the Photodimerization of Anthracene Groups.pdf Macromolecules 2002, 35, 5228-5234 10.1021/ma012263z
42. Defize, T.; Riva, R.; Jéroîme, C.; Alexandre, M. Multifunctional Poly(ϵ-caprolactone)-Forming Networks by Diels-Alder Cycloaddition: Effect of the Adduct on the Shape-Memory Properties Macromol. Chem. Phys. 2012, 213, 187-197 10.1002/macp.201100408
43. Cohn, D.; Hotovely Salomon, A. Designing biodegradable multiblock PCL/PLA thermoplastic elastomers Biomaterials 2005, 26, 2297-2305 10.1016/j.biomaterials.2004.07.052
44. Paul, S.; Halle, O.; Einsiedel, H.; Menges, B.; Mullen, K.; Knoll, W.; Mittler-Neher, S. An anthracene-containing PMMA derivative for photoresist and channel waveguide applications Thin Solid Films 1996, 288, 150-154 10.1016/S0040-6090(96)08823-2