Super Stretchable Electroactive Elastomer Formation Driven by Aniline Trimer Self-Assembly

Chemistry of Materials

Volumn 27, Issue 16, 2015, Pages 5668-5677

  Chen, Jing ^a   Guo, Baolin ^a   Eyster, Thomas W ^b   Ma, Peter X ^a,b  

^a XI'AN JIAOTONG UNIVERSITY   (China)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CARBON; CARBON BLACK; CROSSLINKING; DIFFERENTIAL SCANNING CALORIMETRY; DYNAMIC LIGHT SCATTERING; ELASTOMERS; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HISTOLOGY; LIGHT SCATTERING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; PLASTICS; POLYANILINE; POLYETHYLENE GLYCOLS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; TISSUE; TISSUE REGENERATION; TRANSMISSION ELECTRON MICROSCOPY; UREA;

CHEMICAL CROSS-LINKING; CONDUCTIVE FILLERS; ELASTIC MATERIALS; IONIC CROSS LINKING; NUCLEAR MAGNETIC RESONANCE(NMR); PHYSICAL INTERACTIONS; POLYANILINE NANOFIBERS; POLYURETHANE UREA;

X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84940056669     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.5b02086     Document Type: Article

References (67)

1. Serrano, M. C.; Chung, E. J.; Ameer, G. A. Advances and Applications of Biodegradable Elastomers in Regenerative Medicine Adv. Funct. Mater. 2010, 20, 192-208 10.1002/adfm.200901040
2. Liu, Q. Y.; Jiang, L.; Shi, R.; Zhang, L. Q. Synthesis, preparation, in vitro degradation, and application of novel degradable bioelastomers-A review Prog. Polym. Sci. 2012, 37, 715-765 10.1016/j.progpolymsci.2011.11.001
3. Hung, K.-C.; Tseng, C.-S.; Hsu, S.-h. Synthesis and 3D Printing of Biodegradable Polyurethane Elastomer by a Water-Based Process for Cartilage Tissue Engineering Applications Adv. Healthcare Mater. 2014, 3, 1578-1587 10.1002/adhm.201400018
4. Sasaki, M.; Karikkineth, B. C.; Nagamine, K.; Kaji, H.; Torimitsu, K.; Nishizawa, M. Highly Conductive Stretchable and Biocompatible Electrode-Hydrogel Hybrids for Advanced Tissue Engineering Adv. Healthcare Mater. 2014, 3, 1919-1927 10.1002/adhm.201400209
5. Wang, Y. D.; Ameer, G. A.; Sheppard, B. J.; Langer, R. A tough biodegradable elastomer Nat. Biotechnol. 2002, 20, 602-606 10.1038/nbt0602-602
6. Bruggeman, J. P.; de Bruin, B. J.; Bettinger, C. J.; Langer, R. Biodegradable poly(polyol sebacate) polymers Biomaterials 2008, 29, 4726-4735 10.1016/j.biomaterials.2008.08.037
7. Yang, J.; Webb, A. R.; Ameer, G. A. Novel citric acid-based biodegradable elastomers for tissue engineering Adv. Mater. 2004, 16, 511-516 10.1002/adma.200306264
8. Helminen, A. O.; Korhonen, H.; Seppala, J. V. Cross-linked poly(epsilon-caprolactone/D,L-lactide) copolymers with elastic properties Macromol. Chem. Phys. 2002, 203, 2630-2639 10.1002/macp.200290039
9. Heijkants, R.; van Calck, R. V.; van Tienen, T. G.; de Groot, J. H.; Buma, P.; Pennings, A. J.; Veth, R. P. H.; Schouten, A. J. Uncatalyzed synthesis, thermal and mechanical properties of polyurethanes based on poly(epsilon-caprolactone) and 1,4-butane diisocyanate with uniform hard segment Biomaterials 2005, 26, 4219-4228 10.1016/j.biomaterials.2004.11.005
10. Wang, W. S.; Ping, P.; Yu, H. J.; Chen, X. S.; Jing, X. B. Synthesis and characterization of a novel biodegradable, thermoplastic polyurethane elastomer J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5505-5512 10.1002/pola.21643
11. Borschel, G. H.; Kia, K. F.; Kuzon, W. M.; Dennis, R. G. Mechanical properties of acellular peripheral nerve J. Surg. Res. 2003, 114, 133-139 10.1016/S0022-4804(03)00255-5
12. Monson, K. L.; Goldsmith, W.; Barbaro, N. M.; Manley, G. T. Axial mechanical properties of fresh human cerebral blood vessels J. Biomech. Eng. 2003, 125, 288-294 10.1115/1.1554412
13. Nair, D. P.; Podgorski, M.; Chatani, S.; Gong, T.; Xi, W. X.; Fenoli, C. R.; Bowman, C. N. The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry Chem. Mater. 2014, 26, 724-744 10.1021/cm402180t
14. Gilbert, P. M.; Havenstrite, K. L.; Magnusson, K. E. G.; Sacco, A.; Leonardi, N. A.; Kraft, P.; Nguyen, N. K.; Thrun, S.; Lutolf, M. P.; Blau, H. M. Substrate Elasticity Regulates Skeletal Muscle Stem Cell Self-Renewal in Culture Science 2010, 329, 1078-1081 10.1126/science.1191035
15. Choi, J. S.; Harley, B. A. C. The combined influence of substrate elasticity and ligand density on the viability and biophysical properties of hematopoietic stem and progenitor cells Biomaterials 2012, 33, 4460-4468 10.1016/j.biomaterials.2012.03.010
16. Nassif, N.; Gobeaux, F.; Seto, J.; Belamie, E.; Davidson, P.; Panine, P.; Mosser, G.; Fratzl, P.; Giraud Guille, M. M. Self-Assembled Collagen-Apatite Matrix with Bone-like Hierarchy Chem. Mater. 2010, 22, 3307-3309 10.1021/cm903594n
17. Zhao, B.; Hu, H.; Mandal, S. K.; Haddon, R. C. A bone mimic based on the self-assembly of hydroxyapatite on chemically functionalized single-walled carbon nanotubes Chem. Mater. 2005, 17, 3235-3241 10.1021/cm0500399
18. Zhang, Q. M.; Li, H. F.; Poh, M.; Xia, F.; Cheng, Z. Y.; Xu, H. S.; Huang, C. An all-organic composite actuator material with a high dielectric constant Nature 2002, 419, 284-287 10.1038/nature01021
19. Pelrine, R.; Kornbluh, R.; Pei, Q. B.; Joseph, J. High-speed electrically actuated elastomers with strain greater than 100% Science 2000, 287, 836-839 10.1126/science.287.5454.836
20. Mannsfeld, S. C.; Tee, B. C.; Stoltenberg, R. M.; Chen, C. V. H.; Barman, S.; Muir, B. V.; Sokolov, A. N.; Reese, C.; Bao, Z. Highly sensitive flexible pressure sensors with microstructured rubber dielectric layers Nat. Mater. 2010, 9, 859-864 10.1038/nmat2834
21. Zhai, D. Y.; Liu, B. R.; Shi, Y.; Pan, L. J.; Wang, Y. Q.; Li, W. B.; Zhang, R.; Yu, G. H. Highly Sensitive Glucose Sensor Based on Pt Nanoparticle/Polyaniline Hydrogel Heterostructures ACS Nano 2013, 7, 3540-3546 10.1021/nn400482d
22. Brochu, P.; Pei, Q. B. Advances in Dielectric Elastomers for Actuators and Artificial Muscles Macromol. Rapid Commun. 2010, 31, 10-36 10.1002/marc.200900425
23. Rajagopalan, M.; Oh, I. K. Fullerenol-Based Electroactive Artificial Muscles Utilizing Biocompatible Polyetherimide ACS Nano 2011, 5, 2248-2256 10.1021/nn103521g
24. Shi, G. X.; Rouabhia, M.; Wang, Z. X.; Dao, L. H.; Zhang, Z. A novel electrically conductive and biodegradable composite made of polypyrrole nanoparticles and polylactide Biomaterials 2004, 25, 2477-2488 10.1016/j.biomaterials.2003.09.032
25. Wong, J. Y.; Langer, R.; Ingber, D. E. Electrically conducting polymers can noninvasively control the shape and growth of mammalian cells Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 3201-3204 10.1073/pnas.91.8.3201
26. Guo, B. L.; Glavas, L.; Albertsson, A. C. Biodegradable and electrically conducting polymers for biomedical applications Prog. Polym. Sci. 2013, 38, 1263-1286 10.1016/j.progpolymsci.2013.06.003
27. Bhadra, S.; Khastgir, D.; Singha, N. K.; Lee, J. H. Progress in preparation, processing and applications of polyaniline Prog. Polym. Sci. 2009, 34, 783-810 10.1016/j.progpolymsci.2009.04.003
28. Salvatierra, R. V.; Cava, C. E.; Roman, L. S.; Zarbin, A. J. G. ITO-Free and Flexible Organic Photovoltaic Device Based on High Transparent and Conductive Polyaniline/Carbon Nanotube Thin Films Adv. Funct. Mater. 2013, 23, 1490-1499 10.1002/adfm.201201878
29. Shao, L.; Jeon, J.-W.; Lutkenhaus, J. L. Polyaniline/Vanadium Pentoxide Layer-by-Layer Electrodes for Energy Storage Chem. Mater. 2012, 24, 181-189 10.1021/cm202774n
30. Peng, C.-W.; Hsu, C.-h.; Lin, K.-H.; Li, P.-L.; Hsieh, M.-F.; Wei, Y.; Yeh, J.-M.; Yu, Y.-H. Electrochemical corrosion protection studies of aniline-capped aniline trimer-based electroactive polyurethane coatings Electrochim. Acta 2011, 58, 614-620 10.1016/j.electacta.2011.10.002
31. Guo, B. L.; Finne-Wistrand, A.; Albertsson, A. C. Molecular architecture of electroactive and biodegradable copolymers composed of polylactide and carboxyl-capped aniline trimer Biomacromolecules 2010, 11, 855-863 10.1021/bm9011248
32. Guo, B. L.; Finne-Wistrand, A.; Albertsson, A. C. Degradable and electroactive hydrogels with tunable electrical conductivity and swelling behavior Chem. Mater. 2011, 23, 1254-1262 10.1021/cm103498s
33. Guo, B. L.; Sun, Y.; Finne-Wistrand, A.; Mustafa, K.; Albertsson, A. C. Electroactive tubular porous scaffolds with degradability and non-cytotoxicity for neural tissue regeneration Acta Biomater. 2012, 8, 144-153 10.1016/j.actbio.2011.09.027
34. Wei, Z. X.; Laitinen, T.; Smarsly, B.; Ikkala, O.; Faul, C. F. J. Self-assembly and electrical conductivity transitions in conjugated oligoaniline-Surfactant complexes Angew. Chem., Int. Ed. 2005, 44, 751-756 10.1002/anie.200460928
35. Wang, Y.; Tran, H. D.; Liao, L.; Duan, X. F.; Kaner, R. B. Nanoscale Morphology, Dimensional Control, and Electrical Properties of Oligoanilines J. Am. Chem. Soc. 2010, 132, 10365-10373 10.1021/ja1014184
36. Guo, B.; Finne-Wistrand, A.; Albertsson, A. C. Universal two-step approach to degradable and electroactive block copolymers and networks from combined ring-opening polymerization and post-functionalization via oxidative coupling reactions Macromolecules 2011, 44, 5227-5236 10.1021/ma2009595
37. Gao, J.; Liu, D. G.; Sansiñena, J. M.; Wang, H. L. Synthesis and Characterization of Electrochromic Polyamides with Well-Defined Molecular Structures and Redox Properties Adv. Funct. Mater. 2004, 14, 537-543 10.1002/adfm.200305087
38. Ghosh, K.; Pan, Z.; Guan, E.; Ge, S.; Liu, Y.; Nakamura, T.; Ren, X.-D.; Rafailovich, M.; Clark, R. A. F. Cell adaptation to a physiologically relevant ECM mimic with different viscoelastic properties Biomaterials 2007, 28, 671-679 10.1016/j.biomaterials.2006.09.038
39. Engler, A. J.; Sen, S.; Sweeney, H. L.; Discher, D. E. Matrix Elasticity Directs Stem Cell Lineage Specification Cell 2006, 126, 677-689 10.1016/j.cell.2006.06.044
40. Sun, J. Y.; Zhao, X. H.; Illeperuma, W. R. K.; Chaudhuri, O.; Oh, K. H.; Mooney, D. J.; Vlassak, J. J.; Suo, Z. G. Highly stretchable and tough hydrogels Nature 2012, 489, 133-136 10.1038/nature11409
41. Yang, C. H.; Wang, M. X.; Haider, H.; Yang, J. H.; Sun, J. Y.; Chen, Y. M.; Zhou, J. X.; Suo, Z. G. Strengthening Alginate/Polyacrylamide Hydrogels Using Various Multivalent Cations ACS Appl. Mater. Interfaces 2013, 5, 10418-10422 10.1021/am403966x
42. Ning, J. Y.; Li, G.; Haraguchi, K. Synthesis of Highly Stretchable, Mechanically Tough, Zwitterionic Sulfobetaine Nanocomposite Gels with Controlled Thermosensitivities Macromolecules 2013, 46, 5317-5328 10.1021/ma4009059
43. Chen, B. H.; Lu, J. J.; Yang, C. H.; Yang, J. H.; Zhou, J. X.; Chen, Y. M.; Suo, Z. G. Highly Stretchable and Transparent Ionogels as Nonvolatile Conductors for Dielectric Elastomer Transducers ACS Appl. Mater. Interfaces 2014, 6, 7840-7845 10.1021/am501130t
44. Xia, L. W.; Xie, R.; Ju, X. J.; Wang, W.; Chen, Q. M.; Chu, L. Y. Nano-structured smart hydrogels with rapid response and high elasticity. Nat. Commun. 2013, 4. 10.1038/ncomms3226
45. Cui, Y. L.; Tan, M.; Zhu, A. D.; Guo, M. Y. Mechanically strong and stretchable PEG-based supramolecular hydrogel with water-responsive shape-memory property J. Mater. Chem. B 2014, 2, 2978-2982 10.1039/c4tb00315b
46. Tan, M.; Zhao, T. T.; Huang, H.; Guo, M. Y. Highly stretchable and resilient hydrogels from the copolymerization of acrylamide and a polymerizable macromolecular surfactant Polym. Chem. 2013, 4, 5570-5576 10.1039/c3py00745f
47. Wei, Z.; Yang, J. H.; Zhou, J. X.; Xu, F.; Zrinyi, M.; Dussault, P. H.; Osada, Y.; Chen, Y. M. Self-healing gels based on constitutional dynamic chemistry and their potential applications Chem. Soc. Rev. 2014, 43, 8114-8131 10.1039/C4CS00219A
48. Baker, S. C.; Rohman, G.; Southgate, J.; Cameron, N. R. The relationship between the mechanical properties and cell behaviour on PLGA and PCL scaffolds for bladder tissue engineering Biomaterials 2009, 30, 1321-1328 10.1016/j.biomaterials.2008.11.033
49. Wang, S.; Goh, B. M.; Manga, K. K.; Bao, Q. L.; Yang, P.; Loh, K. P. Graphene as Atomic Template and Structural Scaffold in the Synthesis of Graphene-Organic Hybrid Wire with Photovoltaic Properties ACS Nano 2010, 4, 6180-6186 10.1021/nn101800n
50. Abraham, G. A.; Marcos-Fernández, A.; Román, J. S. Bioresorbable poly (ester-ether urethane)s from L-lysine diisocyanate and triblock copolymers with different hydrophilic character J. Biomed. Mater. Res., Part A 2006, 76, 729-736 10.1002/jbm.a.30540
51. Shi, Y.; van der Meel, R.; Theek, B.; Oude Blenke, E.; Pieters, E. H.; Fens, M. H.; Ehling, J.; Schiffelers, R. M.; Storm, G.; van Nostrum, C. F.; Lammers, T.; Hennink, W. E. Complete Regression of Xenograft Tumors upon Targeted Delivery of Paclitaxel via Pi-Pi Stacking Stabilized Polymeric Micelles ACS Nano 2015, 9, 3740-52 10.1021/acsnano.5b00929
52. Okamoto, T.; Nakahara, K.; Saeki, A.; Seki, S.; Oh, J. H.; Akkerman, H. B.; Bao, Z. N.; Matsuo, Y. Aryl-Perfluoroaryl Substituted Tetracene: Induction of Face-to-Face pi-pi Stacking and Enhancement of Charge Carrier Properties Chem. Mater. 2011, 23, 1646-1649 10.1021/cm200356y
53. Sun, J.-Y.; Zhao, X.; Illeperuma, W. R.; Chaudhuri, O.; Oh, K. H.; Mooney, D. J.; Vlassak, J. J.; Suo, Z. Highly stretchable and tough hydrogels Nature 2012, 489, 133-136 10.1038/nature11409
54. De Groot, J.; De Vrijer, R.; Wildeboer, B.; Spaans, C.; Pennings, A. New biomedical polyurethane ureas with high tear strengths Polym. Bull. 1997, 38, 211-218 10.1007/s002890050040
55. Guo, B.; Finne-Wistrand, A.; Albertsson, A.-C. Simple Route to Size-Tunable Degradable and Electroactive Nanoparticles from the Self-Assembly of Conducting Coil-Rod-Coil Triblock Copolymers Chem. Mater. 2011, 23, 4045-4055 10.1021/cm201782v
56. Huang, L. H.; Hu, J.; Lang, L.; Wang, X.; Zhang, P. B.; Jing, X. B.; Wang, X. H.; Chen, X. S.; Lelkes, P. I.; MacDiarmid, A. G.; Wei, Y. Synthesis and characterization of electroactive and biodegradable ABA block copolymer of polylactide and aniline pentamer Biomaterials 2007, 28, 1741-1751 10.1016/j.biomaterials.2006.12.007
57. Wang, H. F.; Han, Y. C. Vesicles Formed by Oligostyrene-block-Oligoaniline-block-Oligostyrene Triblock Oligomer Macromol. Rapid Commun. 2009, 30, 521-527 10.1002/marc.200800705
58. Xiong, W.; Wang, H. F.; Han, Y. C. Fibrils Formed by Dendron-b-oligoaniline-b-dendron Block Co-oligomer Macromol. Rapid Commun. 2010, 31, 1886-1891 10.1002/marc.201000303
59. Lang, L.; Zhuang, X. L.; Liu, Y. D.; Zhang, P. B.; Chen, X. S.; Wei, Y. Synthesis, Characterization and Self-Assembly of PEG-Aniline Tetramer Block Copolymer Chem. J. Chin. Univ.-Chin. 2011, 32, 411-415
60. Thompson, S. An overview of nickel-titanium alloys used in dentistry Int. Endod. J. 2000, 33, 297-310 10.1046/j.1365-2591.2000.00339.x
61. Trifan, D. S.; Terenzi, J. F. Extents of hydrogen bonding in polyamindes and polyurethanes J. Polym. Sci. 1958, 28, 443-445 10.1126/science.1168242
62. Wei, Y.; Yang, C.; Ding, T. A one-step method to synthesize N, N′-bis (4′-aminophenyl)-1, 4-quinonenediimine and its derivatives Tetrahedron Lett. 1996, 37, 731-734 10.1016/0040-4039(95)02300-3
63. Sun, T. L.; Kurokawa, T.; Kuroda, S.; Ihsan, A. B.; Akasaki, T.; Sato, K.; Haque, M. A.; Nakajima, T.; Gong, J. P. Physical hydrogels composed of polyampholytes demonstrate high toughness and viscoelasticity Nat. Mater. 2013, 12, 932-937 10.1038/nmat3713
64. Saito, T.; Furuta, T.; Hwang, J.-H.; Kuramoto, S.; Nishino, K.; Suzuki, N.; Chen, R.; Yamada, A.; Ito, K.; Seno, Y.; Nonaka, T.; Ikehata, H.; Nagasako, N.; Iwamoto, C.; Ikuhara, Y.; Sakuma, T. Multifunctional Alloys Obtained via a Dislocation-Free Plastic Deformation Mechanism Science 2003, 300, 464-467 10.1126/science.1081957
65. Kim, B. S.; Park, S. W.; Hammond, P. T. Hydrogen-bonding layer-by-layer assembled biodegradable polymeric micelles as drug delivery vehicles from surfaces ACS Nano 2008, 2, 386-392 10.1021/nn700408z
66. Lin, Y. F.; Chen, C. H.; Xie, W. J.; Yang, S. H.; Hsu, C. S.; Lin, M. T.; Jian, W. B. Nano Approach Investigation of the Conduction Mechanism in Polyaniline Nanofibers ACS Nano 2011, 5, 1541-1548 10.1021/nn103525b
67. Huang, J. X.; Kaner, R. B. A general chemical route to polyaniline nanofibers J. Am. Chem. Soc. 2004, 126, 851-855 10.1021/ja0371754