Healable supramolecular polymer solids

Progress in Polymer Science

Volumn 49-50, Issue , 2015, Pages 60-78

  De Espinosa, Lucas Montero ^a   Fiore, Gina L ^a   Weder, Christoph ^a   Johan Foster, E ^b   Simon, Yoan C ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

^b Virginia Polytechnic Institute and State University   (United States)

Author keywords

Healable polymer; Hydrogen bonding; Metallosupramolecular; Self healing; Supramolecular nanocomposite; Supramolecular polymer

Indexed keywords

CROSSLINKING; HYDROGEN BONDS; NANOCOMPOSITES; SUPRAMOLECULAR CHEMISTRY;

CROSS-LINK DENSITIES; CROSS-LINKED POLYMERS; EXTERNAL STIMULUS; METALLO-SUPRAMOLECULAR; NON-COVALENT INTERACTION; SELF-HEALING; SUPRAMOLECULAR NANOCOMPOSITES; SUPRAMOLECULAR POLYMERS;

POLYMERS;

EID: 84941808111     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2015.04.003     Document Type: Review

References (111)

1. S.D. Bergman, and F. Wudl Mendable polymers J Mater Chem 18 2008 41 62
2. S. Burattini, B.W. Greenland, D. Chappell, H.M. Colquhoun, and W. Hayes Healable polymeric materials: a tutorial review Chem Soc Rev 39 2010 1973 1985
3. E.B. Murphy, and F. Wudl The world of smart healable materials Prog Polym Sci 35 2010 223 251
4. M.W. Urban Stratification, stimuli-responsiveness, self-healing, and signaling in polymer networks Prog Polym Sci 34 2009 679 687
5. B.J. Blaiszik, S.L.B. Kramer, S.C. Olugebefola, J.S. Moore, N.R. Sottos, and S.R. White Self-healing polymers and composites Annu Rev Mater Res 40 2010 179 211
6. R.P. Wool Self-healing materials: a review Soft Matter 4 2008 400 418
7. S. Seiffert, and J. Sprakel Physical chemistry of supramolecular polymer networks Chem Soc Rev 41 2012 909 930
8. D.Y. Wu, S. Meure, and D. Solomon Self-healing polymeric materials: a review of recent developments Prog Polym Sci 33 2008 479 522
9. J.A. Syrett, C.R. Becer, and D.M. Haddleton Self-healing and self-mendable polymers Polym Chem 1 2010 978 987
10. K. Jud, H.H. Kausch, and J.G. Williams Fracture mechanics studies of crack healing and welding of polymers J Mater Sci 16 1981 204 210
11. Y.H. Kim, and R.P. Wool A theory of healing at a polymer-polymer interface Macromolecules 16 1983 1115 1120
12. S.R. White, N.R. Sottos, P.H. Geubelle, J.S. Moore, M.R. Kessler, S.R. Sriram, E.N. Brown, and S. Viswanathan Autonomic healing of polymer composites Nature 409 2001 794 797
13. K.S. Toohey, N.R. Sottos, J.A. Lewis, J.S. Moore, and S.R. White Self-healing materials with microvascular networks Nat Mater 6 2007 581 585
14. A.P. Esser-Kahn, S.A. Odom, N.R. Sottos, S.R. White, and J.S. Moore Triggered release from polymer capsules Macromolecules 44 2011 5539 5553
15. X. Chen, M.A. Dam, K. Ono, A. Mal, H. Shen, S.R. Nutt, K. Sheran, and F. Wudl A thermally re-mendable cross-linked polymeric material Science 295 2002 1698 1702
16. R.P. Sijbesma, F.H. Beijer, L. Brunsveld, B.J.B. Folmer, J.H.K. Hirschberg, R.F.M. Lange, J.K.L. Lowe, and E.W. Meijer Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding Science 278 1997 1601 1604
17. R.A. Koevoets, R.M. Versteegen, H. Kooijman, A.L. Spek, R.P. Sijbesma, and E.W. Meijer Molecular recognition in a thermoplastic elastomer J Am Chem Soc 127 2005 2999 3003
18. R.M. Versteegen, R.P. Sijbesma, and E.W. Meijer Synthesis and characterization of segmented copoly(ether urea)s with uniform hard segments Macromolecules 38 2005 3176 3184
19. E. Wisse, L.E. Govaert, H.E.H. Meijer, and E.W. Meijer Unusual tuning of mechanical properties of thermoplastic elastomers using supramolecular fillers Macromolecules 39 2006 7425 7432
20. N.E. Botterhuis, S. Karthikeyan, D. Veldman, S.C.J. Meskers, and R.P. Sijbesma Molecular recognition in bisurea thermoplastic elastomers studied with pyrene-based fluorescent probes and atomic force microscopy Chem Commun 2008 3915 3917
21. N.E. Botterhuis, S. Karthikeyan, A.J.H. Spiering, and R.P. Sijbesma Self-sorting of guests and hard blocks in bisurea-based thermoplastic elastomers Macromolecules 43 2009 745 751
22. C. Fouquey, J.M. Lehn, and A.M. Levelut Molecular recognition directed self-assembly of supramolecular liquid crystalline polymers from complementary chiral components Adv Mater 2 1990 254 257
23. C.M. Lee, C. Jariwala, and A. Griffin Heteromeric liquid-crystalline association chain polymers: structure and properties Polymer 35 1994 4550 4554
24. C.B. St Pourcain, and A.C. Griffin Thermoreversible supramolecular networks with polymeric properties Macromolecules 28 1995 4116 4121
25. L. Brunsveld, B.J.B. Folmer, E.W. Meijer, and R.P. Sijbesma Supramolecular polymers Chem Rev 101 2001 4071 4098
26. L. Fang, M.A. Olson, D. Benitez, E. Tkatchouk, W.A. Goddard, and J.F. Stoddart Mechanically bonded macromolecules Chem Soc Rev 39 2010 17 29
27. C.A. Hunter, M.N. Meah, and J.K.M. Sanders Dabco metalloporphyrin binding - ternary complexes, host guest chemistry, and the measurement of Pi-Pi-interactions J Am Chem Soc 112 1990 5773 5780
28. M. Burnworth, D. Knapton, S. Rowan, and C. Weder Metallo-supramolecular polymerization: a route to easy-to-process organic/inorganic hybrid materials J Inorg Organomet Polym Mater 17 2007 91 103
29. A. Harada Supramolecular polymer chemistry 2012 John Wiley & Sons New York 390
30. R.J. Wojtecki, M.A. Meador, and S.J. Rowan Using the dynamic bond to access macroscopically responsive structurally dynamic polymers Nat Mater 10 2011 14 27
31. X. Yan, F. Wang, B. Zheng, and F. Huang Stimuli-responsive supramolecular polymeric materials Chem Soc Rev 41 2012 6042 6065
32. S. Sivakova, D.A. Bohnsack, M.E. Mackay, P. Suwanmala, and S.J. Rowan Utilization of a combination of weak hydrogen-bonding interactions and phase segregation to yield highly thermosensitive supramolecular polymers J Am Chem Soc 127 2005 18202 18211
33. X. Ma, R. Sun, W. Li, and H. Tian Novel electrochemical and pH stimulus-responsive supramolecular polymer with disparate pseudorotaxanes as relevant unimers Polym Chem 2 2011 1068 1070
34. M. Burnworth, L. Tang, J.R. Kumpfer, A.J. Duncan, F.L. Beyer, G.L. Fiore, S.J. Rowan, and C. Weder Optically healable supramolecular polymers Nature 472 2011 334 337
35. D.W.R. Balkenende, S. Coulibaly, S. Balog, Y.C. Simon, G.L. Fiore, and C. Weder Mechanochemistry with metallosupramolecular polymers J Am Chem Soc 136 2014 10493 10498
36. J.R. Kumpfer, and S.J. Rowan Thermo-, photo-, and chemo-responsive shape-memory properties from photo-cross-linked metallo-supramolecular polymers J Am Chem Soc 133 2011 12866 12874
37. C. Heinzmann, S. Coulibaly, A. Roulin, G.L. Fiore, and C. Weder Light-induced bonding and debonding with supramolecular adhesives ACS Appl Mater Interfaces 6 2014 4713 4719
38. A.W. Bosman, R.P. Sijbesma, and E.W. Meijer Supramolecular polymers at work Mater Today 7 2004 34 39
39. P. Cordier, F. Tournilhac, C. Soulie-Ziakovic, and L. Leibler Self-healing and thermoreversible rubber from supramolecular assembly Nature 451 2008 977 980
40. Y. Chen, A.M. Kushner, G.A. Williams, and Z. Guan Multiphase design of autonomic self-healing thermoplastic elastomers Nat Chem 4 2012 467 472
41. G.M.L. van Gemert, J.W. Peeters, S.H.M. Söntjens, H.M. Janssen, and A.W. Bosman Self-healing supramolecular polymers in action Macromol Chem Phys 213 2012 234 242
42. G.L. Fiore, S.J. Rowan, and C. Weder Optically healable polymers Chem Soc Rev 42 2013 7278 7288
43. J. Kotteritzsch, U.S. Schubert, and M.D. Hager Triggered and self-healing systems using nanostructured materials Nanotechnol Rev 2 2013 699 723
44. S.J. Benight, C. Wang, J.B.H. Tok, and Z.A. Bao Stretchable and self-healing polymers and devices for electronic skin Prog Polym Sci 38 2013 1961 1977
45. H. Colquhoun, and B. Klumperman Self-healing polymers Polym Chem 4 2013 4832 4833
46. L.R. Hart, J.L. Harries, B.W. Greenland, H.M. Colquhoun, and W. Hayes Healable supramolecular polymers Polym Chem 4 2013 4860 4870
47. F. Herbst, D. Dohler, P. Michael, and W.H. Binder Self-healing polymers via supramolecular forces Macromol Rapid Commun 34 2013 203 220
48. B. Sandmann, S. Bode, M.D. Hager, and U.S. Schubert Metallopolymers as an emerging class of self-healing materials Adv Polym Sci 262 2013 239 257
49. A. Harada, Y. Takashima, and M. Nakahata Supramolecular polymeric materials via cyclodextrin-guest interactions Acc Chem Res 47 2014 2128 2140
50. Z. Qi, and C.A. Schalley Exploring macrocycles in functional supramolecular gels: from stimuli responsiveness to systems chemistry Acc Chem Res 47 2014 2222 2233
51. S. Dong, B. Zheng, F. Wang, and F. Huang Supramolecular polymers constructed from macrocycle-based host-guest molecular recognition motifs Acc Chem Res 47 2014 1982 1994
52. J. Brassinne, C.A. Fustin, and J.F. Gohy Polymer gels constructed through metal-ligand coordination J Inorg Organomet Polym 23 2013 24 40
53. E. Krieg, and B. Rybtchinski Noncovalent water-based materials: robust yet adaptive Chem Eur J 17 2011 9016 9026
54. D.K. Smith Supramolecular gels: building bridges Nat Chem 2 2010 162 163
55. Y. Yang, and M.W. Urban Self-healing polymeric materials Chem Soc Rev 42 2013 7446 7467
56. M.A. Aboudzadeh, M.E. Muñoz, A. Santamaría, R. Marcilla, and D. Mecerreyes Facile synthesis of supramolecular ionic polymers that combine unique rheological, ionic conductivity, and self-healing properties Macromol Rapid Commun 33 2012 314 318
57. A. Aboudzadeh, M. Fernandez, M.E. Muñoz, A. Santamaría, and D. Mecerreyes Ionic supramolecular networks fully based on chemicals coming from renewable sources Macromol Rapid Commun 35 2014 460 465
58. G.A. Jeffrey, and W. Saenger Hydrogen bonding in biological structures 2nd ed. 1994 Springer-Verlag Heidelberg 584
59. G.M.L. Hoorne-Van Gemert, H.M. Janssen, E.W. Meijer, and A.W. Bosman Supramolecular polymers from low-melting, easily processable building blocks 2008 EP 2087027B1
60. J.H.K.K. Hirschberg, F.H. Beijer, H.A. van Aert, P.C.M.M. Magusin, R.P. Sijbesma, and E.W. Meijer Supramolecular polymers from linear telechelic siloxanes with quadruple-hydrogen-bonded units Macromolecules 32 1999 2696 2705
61. B.J.B. Folmer, R.P. Sijbesma, R.M. Versteegen, J.A.J. van der Rijt, and E.W. Meijer Supramolecular polymer materials: chain extension of telechelic polymers using a reactive hydrogen-bonding synthon Adv Mater 12 2000 874 878
62. K. Chino, and M. Ashiura Themoreversible cross-linking rubber using supramolecular hydrogen-bonding networks Macromolecules 34 2001 9201 9204
63. S.J. Rowan, P. Suwanmala, and S. Sivakova Nucleobase-induced supramolecular polymerization in the solid state J Polym Sci A: Polym Chem 41 2003 3589 3596
64. N.E. Botterhuis, D.J.M. van Beek, G.M.L. van Gemert, A.W. Bosman, and R.P. Sijbesma Self-assembly and morphology of polydimethylsiloxane supramolecular thermoplastic elastomers J Polym Sci A: Polym Chem 46 2008 3877 3885
65. D. Montarnal, P. Cordier, C. Soulié-Ziakovic, F. Tournilhac, and L. Leibler Synthesis of self-healing supramolecular rubbers from fatty acid derivatives, diethylene triamine, and urea J Polym Sci A: Polym Chem 46 2008 7925 7936
66. D. Montarnal, F. Tournilhac, M. Hidalgo, J.L. Couturier, and L. Leibler Versatile one-pot synthesis of supramolecular plastics and self-healing rubbers J Am Chem Soc 131 2009 7966 7967
67. A. Zhang, L. Yang, Y. Lin, L. Yan, H. Lu, and L. Wang Self-healing supramolecular elastomers based on the multi-hydrogen bonding of low-molecular polydimethylsiloxanes: synthesis and characterization J Appl Polym Sci 129 2013 2435 2442
68. F. Maes, D. Montarnal, S. Cantournet, F. Tournilhac, L. Corte, and L. Leibler Activation and deactivation of self-healing in supramolecular rubbers Soft Matter 8 2012 1681 1687
69. R. Zhang, T. Yan, B.D. Lechner, K. Schröter, Y. Liang, B. Li, F. Furtado, P. Sun, and K. Saalwächter Heterogeneity, segmental and hydrogen bond dynamics, and aging of supramolecular self-healing rubber Macromolecules 46 2013 1841 1850
70. Y. Chen, and Z. Guan Self-assembly of core-shell nanoparticles for self-healing materials Polym Chem 4 2013 4885 4889
71. J. Hentschel, A.M. Kushner, J. Ziller, and Z. Guan Self-healing supramolecular block copolymers Angew Chem Int Ed Engl 51 2012 10561 10565
72. Y. Chen, and Z. Guan Multivalent hydrogen bonding block copolymers self-assemble into strong and tough self-healing materials Chem Commun 50 2014 10868 10870
73. A. Faghihnejad, K.E. Feldman, J. Yu, M.V. Tirrell, J.N. Israelachvili, C.J. Hawker, E.J. Kramer, and H. Zeng Adhesion and surface interactions of a self-healing polymer with multiple hydrogen-bonding groups Adv Funct Mater 24 2014 2322 2333
74. Q. Wei, C. Schlaich, S. Prévost, A. Schulz, C. Böttcher, M. Gradzielski, Z. Qi, R. Haag, and C.A. Schalley Supramolecular polymers as surface coatings: rapid fabrication of healable superhydrophobic and slippery surfaces Adv Mater 26 2014 7358 7364
75. F. Herbst, S. Seiffert, and W.H. Binder Dynamic supramolecular poly(isobutylene)s for self-healing materials Polym Chem 3 2012 3084 3092
76. N. Roy, E. Buhler, and J.M. Lehn The tris-urea motif and its incorporation into polydimethylsiloxane-based supramolecular materials presenting self-healing features Chem Eur J 19 2013 8814 8820
77. N. Roy, E. Buhler, and J.M. Lehn Double dynamic self-healing polymers: supramolecular and covalent dynamic polymers based on the bis-iminocarbohydrazide motif Polym Int 63 2014 1400 1405
78. G.L. Fiore, S.J. Rowan, and C. Weder Light-activated healing of metallosupramolecular materials Chimia 65 2011 745
79. J.R. Kumpfer, J.J. Wie, J.P. Swanson, F.L. Beyer, M.E. Mackay, and S.J. Rowan Influence of metal ion and polymer core on the melt rheology of metallosupramolecular films Macromolecules 45 2011 473 480
80. D. Knapton, M. Burnworth, S.J. Rowan, and C. Weder Fluorescent organometallic sensors for the detection of chemical-warfare-agent mimics Angew Chem Int Ed Engl 45 2006 5825 5829
81. J.R. Kumpfer, J. Jin, and S.J. Rowan Stimuli-responsive europium-containing metallo-supramolecular polymers J Mater Chem 20 2010 145 151
82. G. Hong, H. Zhang, Y. Lin, Y. Chen, Y. Xu, W. Weng, and H. Xia Mechanoresponsive healable metallosupramolecular polymers Macromolecules 46 2013 8649 8656
83. B. Yang, H. Zhang, H. Peng, Y. Xu, B. Wu, W. Weng, and L. Li Self-healing metallo-supramolecular polymers from a ligand macromolecule synthesized via copper-catalyzed azide-alkyne cycloaddition and thiol-ene double "click" reactions Polym Chem 5 2014 1945 1953
84. Z. Wang, W. Fan, R. Tong, X. Lu, and H. Xia Thermal-healable and shape memory metallosupramolecular poly(n-butyl acrylate-co-methyl methacrylate) materials RSC Adv 4 2014 25486 25493
85. S. Bode, R.K. Bose, S. Matthes, M. Ehrhardt, A. Seifert, F.H. Schacher, R.M. Paulus, S. Stumpf, B. Sandmann, J. Vitz, A. Winter, S. Hoeppener, S.J. Garcia, S. Spange, S. van der Zwaag, M.D. Hager, and U.S. Schubert Self-healing metallopolymers based on cadmium bis(terpyridine) complex containing polymer networks Polym Chem 4 2013 4966 4973
86. S. Bode, L. Zedler, F.H. Schacher, B. Dietzek, M. Schmitt, J. Popp, M.D. Hager, and U.S. Schubert Self-healing polymer coatings based on crosslinked metallosupramolecular copolymers Adv Mater 25 2013 1634 1638
87. S. Kupfer, L. Zedler, J. Guthmuller, S. Bode, M.D. Hager, U.S. Schubert, J. Popp, S. Grafe, and B. Dietzek Self-healing mechanism of metallopolymers investigated by QM/MM simulations and Raman spectroscopy Phys Chem Chem Phys 16 2014 12422 12432
88. L. Zedler, M.D. Hager, U.S. Schubert, M.J. Harrington, M. Schmitt, J. Popp, and B. Dietzek Monitoring the chemistry of self-healing by vibrational spectroscopy - current state and perspectives Mater Today 17 2014 57 69
89. Z. Wang, and M.W. Urban Facile UV-healable polyethylenimine-copper (C2H5N-Cu) supramolecular polymer networks Polym Chem 4 2013 4897 4901
90. C.A. Hunter, and J.K.M. Sanders The nature of Pi-Pi interactions J Am Chem Soc 112 1990 5525 5534
91. C.R. Martinez, and B.L. Iverson Rethinking the term "pi-stacking" Chem Sci 3 2012 2191 2201
92. H.M. Colquhoun, E.P. Goodings, J.M. Maud, J.F. Stoddart, J.B. Wolstenholme, and D.J. Williams The complexation of the diquat dication by dibenzo-3n-crown-N ethers J Chem Soc Perk Trans 2 1985 607 624
93. V. Nandwana, I. Samuel, G. Cooke, and V.M. Rotello Aromatic stacking interactions in Flavin model systems Acc Chem Res 46 2013 1000 1009
94. T. Okazaki, and K.K. Laali Transannular pi-pi interactions in janusenes and in related rigid systems with cofacial aromatic rings; gauging aromaticity in the hydrocarbons and in model carbocations; a DFT study Org Biomol Chem 4 2006 3085 3095
95. M.L. Waters Aromatic interactions in model systems Curr Opin Chem Biol 6 2002 736 741
96. B.W. Greenland, S. Burattini, W. Hayes, and H.M. Colquhoun Design, synthesis and computational modelling of aromatic tweezer-molecules as models for chain-folding polymer blends Tetrahedron 64 2008 8346 8354
97. S. Burattini, H.M. Colquhoun, B.W. Greenland, and W. Hayes A novel self-healing supramolecular polymer system Faraday Discuss 143 2009 251 264
98. S. Burattini, H.M. Colquhoun, J.D. Fox, D. Friedmann, B.W. Greenland, P.J.F. Harris, W. Hayes, M.E. Mackay, and S.J. Rowan A self-repairing, supramolecular polymer system: healability as a consequence of donor-acceptor pi-pi stacking interactions Chem Commun 2009 6717 6719
99. S. Burattini, B.W. Greenland, W. Hayes, M.E. Mackay, S.J. Rowan, and H.M. Colquhoun A supramolecular polymer based on tweezer-type pi-pi stacking interactions: molecular design for healability and enhanced toughness Chem Mater 23 2011 6 8
100. S. Burattini, B.W. Greenland, D.H. Merino, W.G. Weng, J. Seppala, H.M. Colquhoun, W. Hayes, M.E. Mackay, I.W. Hamley, and S.J. Rowan A healable supramolecular polymer blend based on aromatic pi-pi stacking and hydrogen-bonding interactions J Am Chem Soc 132 2010 12051 12058
101. L.R. Hart, J.H. Hunter, N.A. Nguyen, J.L. Harries, B.W. Greenland, M.E. Mackay, H.M. Colquhoun, and W. Hayes Multivalency in healable supramolecular polymers: the effect of supramolecular cross-link density on the mechanical properties and healing of non-covalent polymer networks Polym Chem 5 2014 3680 3688
102. R. Vaiyapuri, B.W. Greenland, H.M. Colquhoun, J.M. Elliott, and W. Hayes Evolution of supramolecular healable composites: a minireview Polym Int 63 2014 933 942
103. J. Fox, J.J. Wie, B.W. Greenland, S. Burattini, W. Hayes, H.M. Colquhoun, M.E. Mackay, and S.J. Rowan High-strength, healable, supramolecular polymer nanocomposites J Am Chem Soc 134 2012 5362 5368
104. R.J. Moon, A. Martini, J. Nairn, J. Simonsen, and J. Youngblood Cellulose nanomaterials review: structure, properties and nanocomposites Chem Soc Rev 40 2011 3941 3994
105. S.J. Eichhorn, A. Dufresne, M. Aranguren, N.E. Marcovich, J.R. Capadona, S.J. Rowan, C. Weder, W. Thielemans, M. Roman, S. Renneckar, W. Gindl, S. Veigel, J. Keckes, H. Yano, K. Abe, M. Nogi, A.N. Nakagaito, A. Mangalam, J. Simonsen, A.S. Benight, A. Bismarck, L.A. Berglund, and T. Peijs Review: current international research into cellulose nanofibres and nanocomposites J Mater Sci 45 2010 1 33
106. S. Coulibaly, A. Roulin, S. Balog, M.V. Biyani, E.J. Foster, S.J. Rowan, G.L. Fiore, and C. Weder Reinforcement of optically healable supramolecular polymers with cellulose nanocrystals Macromolecules 47 2013 152 160
107. O. van den Berg, J.R. Capadona, and C. Weder Preparation of homogeneous dispersions of tunicate cellulose whiskers in organic solvents Biomacromolecules 8 2007 1353 1357
108. G. Siqueira, J. Bras, and A. Dufresne Cellulose whiskers versus microfibrils: influence of the nature of the nanoparticle and its surface functionalization on the thermal and mechanical properties of nanocomposites Biomacromolecules 10 2009 425 432
109. M.V. Biyani, E.J. Foster, and C. Weder Light-healable supramolecular nanocomposites based on modified cellulose nanocrystals ACS Macro Lett 2 2013 236 240
110. R. Vaiyapuri, B.W. Greenland, S.J. Rowan, H.M. Colquhoun, J.M. Elliott, and W. Hayes Thermoresponsive supramolecular polymer network comprising pyrene-functionalized gold nanoparticles and a chain-folding polydiimide Macromolecules 45 2012 5567 5574
111. R. Vaiyapuri, B.W. Greenland, H.M. Colquhoun, J.M. Elliott, and W. Hayes Molecular recognition between functionalized gold nanoparticles and healable, supramolecular polymer blends - a route to property enhancement Polym Chem 4 2013 4902 4909