PH Responsive and Oxidation Resistant Wet Adhesive based on Reversible Catechol-Boronate Complexation

Chemistry of Materials

Volumn 28, Issue 15, 2016, Pages 5432-5439

  Narkar, Ameya R ^a   Barker, Brett ^a   Clisch, Matthew ^a   Jiang, Jingfeng ^a   Lee, Bruce P ^a  

^a Michigan Technological University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADHESION; BINDING ENERGY; BINS; COMPLEX NETWORKS; DEFORMATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; OXIDATION RESISTANCE; PHENOLS; SILANES; WETTING;

ADHESIVE PROPERTIES; CROSS-LINKING DENSITY; INTERFACIAL BINDING; JOHNSON-KENDALL-ROBERTS; OXIDATION RESISTANT; PHENYLBORONIC ACIDS; REVERSIBLE COMPLEXATION; VISCOUS DISSIPATION;

BOROSILICATE GLASS;

EID: 84981554893     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.6b01851     Document Type: Article

References (52)

1. Heinzmann, C.; Coulibaly, S.; Roulin, A.; Fiore, G. L.; Weder, C. Light-Induced Bonding and Debonding with Supramolecular Adhesives ACS Appl. Mater. Interfaces 2014, 6 (7) 4713-4719 10.1021/am405302z
2. Northen, M. T.; Greiner, C.; Arzt, E.; Turner, K. L. A Gecko-Inspired Reversible Adhesive Adv. Mater. 2008, 20 (20) 3905-3909 10.1002/adma.200801340
3. Luo, X.; Lauber, K. E.; Mather, P. T. A thermally responsive, rigid, and reversible adhesive Polymer 2010, 51 (5) 1169-1175 10.1016/j.polymer.2010.01.006
4. Banea, M.; da Silva, L.; Campilho, R. An overview of the technologies for adhesive debonding on command Annals of "Dunarea de Jos" University of Galati. Fascicle XII: Welding Equipment and Technology 2013, 24, 11-14
5. Sudre, G.; Olanier, L.; Tran, Y.; Hourdet, D.; Creton, C. Reversible adhesion between a hydrogel and a polymer brush Soft Matter 2012, 8 (31) 8184-8193 10.1039/c2sm25868d
6. Comyn, J. The relationship between joint durability and water diffusion. In Developments in Adhesives; Kinloch, A. J., Ed.; Applied Science Publishers: Barking, U.K., 1981; Vol. 2, pp 279-313.
7. Lee, B. P.; Messersmith, P. B.; Israelachvili, J. N.; Waite, J. H. Mussel-Inspired Adhesives and Coatings Annu. Rev. Mater. Res. 2011, 41, 99-132 10.1146/annurev-matsci-062910-100429
8. Waite, J. H. Nature's underwater adhesive specialist Int. J. Adhes. Adhes. 1987, 7 (1) 9-14 10.1016/0143-7496(87)90048-0
9. Yamamoto, H. Marine adhesive proteins and some biotechnological applications Biotechnol. Genet. Eng. Rev. 1996, 13, 133-166 10.1080/02648725.1996.10647926
10. Meredith, H. J.; Wilker, J. J. The Interplay of Modulus, Strength, and Ductility in Adhesive Design Using Biomimetic Polymer Chemistry Adv. Funct. Mater. 2015, 25 (31) 5057-5065 10.1002/adfm.201501880
11. Pechey, A.; Elwood, C. N.; Wignall, G. R.; Dalsin, J. L.; Lee, B. P.; Vanjecek, M.; Welch, I.; Ko, R.; Razvi, H.; Cadieux, P. A. Anti-adhesive coating and clearance of device associated uropathogenic escherichia coli cystitis J. Urol. (N. Y., NY, U. S.) 2009, 182 (4) 1628-1636 10.1016/j.juro.2009.06.008
12. Liu, Y.; Meng, H.; Konst, S.; Sarmiento, R.; Rajachar, R.; Lee, B. P. Injectable Dopamine-Modified Poly(Ethylene Glycol) Nanocomposite Hydrogel with Enhanced Adhesive Property and Bioactivity ACS Appl. Mater. Interfaces 2014, 6 (19) 16982-16992 10.1021/am504566v
13. Ejima, H.; Richardson, J. J.; Liang, K.; Best, J. P.; van Koeverden, M. P.; Such, G. K.; Cui, J.; Caruso, F. One-step assembly of coordination complexes for versatile film and particle engineering Science 2013, 341 (6142) 154-157 10.1126/science.1237265
14. Holten-Andersen, N.; Harrington, M. J.; Birkedal, H.; Lee, B. P.; Messersmith, P. B.; Lee, K. Y. C.; Waite, J. H. pH-induced mussel metal-ligand crosslinks yield self-healing polymer networks with near-covalent elastic moduli Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 2651-2655 10.1073/pnas.1015862108
15. Lee, B. P.; Konst, S. Novel hydrogel actuator inspired by reversible mussel adhesive protein chemistry Adv. Mater. 2014, 26 (21) 3415-3419 10.1002/adma.201306137
16. Lee, B. P.; Lin, M.-H.; Narkar, A.; Konst, S.; Wilharm, R. Modulating the Movement of Hydrogel Actuator based on Catechol-Iron Ion Coordination Chemistry Sens. Actuators, B 2015, 206, 456-462 10.1016/j.snb.2014.09.089
17. Lee, B. P.; Narkar, A.; Wilharm, R. Effect of metal ion type on the movement of hydrogel actuator based on catechol-metal ion coordination chemistry Sens. Actuators, B 2016, 227, 248-254 10.1016/j.snb.2015.12.038
18. Guo, J. L.; Ping, Y.; Ejima, H.; Alt, K.; Meissner, M.; Richardson, J. J.; Yan, Y.; Peter, K.; von Elverfeldt, D.; Hagemeyer, C. E.; Caruso, F. Engineering Multifunctional Capsules through the Assembly of Metal-Phenolic Networks Angew. Chem., Int. Ed. 2014, 53 (22) 5546-5551 10.1002/anie.201311136
19. Wilke, P.; Helfricht, N.; Mark, A.; Papastavrou, G.; Faivre, D.; Börner, H. G. A Direct Biocombinatorial Strategy toward Next Generation, Mussel-Glue Inspired Saltwater Adhesives J. Am. Chem. Soc. 2014, 136 (36) 12667-12674 10.1021/ja505413e
20. Shafiq, Z.; Cui, J.; Pastor-Pérez, L.; San Miguel, V.; Gropeanu, R. A.; Serrano, C.; del Campo, A. Bioinspired Underwater Bonding and Debonding on Demand Angew. Chem., Int. Ed. 2012, 51 (18) 4332-4335 10.1002/anie.201108629
21. Yu, M.; Hwang, J.; Deming, T. J. Role of l-3,4-Dihydroxyphenylalanine in Mussel Adhesive Proteins J. Am. Chem. Soc. 1999, 121 (24) 5825-5826 10.1021/ja990469y
22. Lee, B. P.; Chao, C.-Y.; Nunalee, F. N.; Motan, E.; Shull, K. R.; Messersmith, P. B. Rapid Gel Formation and Adhesion in Photocurable and Biodegradable Block Copolymers with High DOPA Content Macromolecules (Washington, DC, U. S.) 2006, 39 (5) 1740-1748 10.1021/ma0518959
23. Yu, J.; Wei, W.; Menyo, M. S.; Masic, A.; Waite, J. H.; Israelachvili, J. N. Adhesion of Mussel Foot Protein-3 to TiO2 Surfaces: the Effect of pH Biomacromolecules 2013, 14 (4) 1072-1077 10.1021/bm301908y
24. Lee, H.; Scherer, N. F.; Messersmith, P. B. Single-molecule mechanics of mussel adhesion Proc. Natl. Acad. Sci. U. S. A. 2006, 103 (35) 12999-13003 10.1073/pnas.0605552103
25. Yang, J.; Cohen Stuart, M. A.; Kamperman, M. Jack of all trades: versatile catechol crosslinking mechanisms Chem. Soc. Rev. 2014, 43 (24) 8271-8298 10.1039/C4CS00185K
26. Lee, B. P.; Dalsin, J. L.; Messersmith, P. B. Synthesis and Gelation of DOPA-Modified Poly(ethylene glycol) Hydrogels Biomacromolecules 2002, 3 (5) 1038-1047 10.1021/bm025546n
27. Pizer, R.; Babcock, L. Mechanism of Complexation of Boron Acids with Catechol and Substituted Catechols Inorg. Chem. 1977, 16 (7) 1677-1681 10.1021/ic50173a021
28. He, L.; Fullenkamp, D. E.; Rivera, J. G.; Messersmith, P. B. pH responsive self-healing hydrogels formed by boronate-catechol complexation Chem. Commun. 2011, 47, 7497-7499 10.1039/c1cc11928a
29. Huang, K.; Lee, B. P.; Ingram, D.; Messersmith, P. B. Synthesis and Characterization of Self-Assembling Block Copolymers Containing Bioadhesive End Groups Biomacromolecules 2002, 3 (2) 397-406 10.1021/bm015650p
30. Kan, Y.; Danner, E. W.; Israelachvili, J. N.; Chen, Y.; Waite, J. H. Boronate Complex Formation with Dopa Containing Mussel Adhesive Protein Retards pH-Induced Oxidation and Enables Adhesion to Mica PLoS One 2014, 9 (10) e108869 10.1371/journal.pone.0108869
31. Guo, J.; Sun, H.; Alt, K.; Tardy, B. L.; Richardson, J. J.; Suma, T.; Ejima, H.; Cui, J.; Hagemeyer, C. E.; Caruso, F. Boronate-Phenolic Network Capsules with Dual Response to Acidic pH and cis-Diols Adv. Healthcare Mater. 2015, 4 (12) 1796-1801 10.1002/adhm.201500332
32. Lee, H.; Lee, B. P.; Messersmith, P. B. A reversible wet/dry adhesive inspired by mussels and geckos Nature (London, U. K.) 2007, 448 (7151) 338-341 10.1038/nature05968
33. Bryant, S. J.; Anseth, K. S. Hydrogel properties influence ECM production by chondrocytes photoencapsulated in poly(ethylene glycol) hydrogels J. Biomed. Mater. Res. 2002, 59 (1) 63-72 10.1002/jbm.1217
34. Yang, F. K.; Zhang, W.; Han, Y.; Yoffe, S.; Cho, Y.; Zhao, B. Contact" of Nanoscale Stiff Films Langmuir 2012, 28 (25) 9562-9572 10.1021/la301388e
35. Flanigan, C. M.; Crosby, A. J.; Shull, K. R. Structural development and adhesion of acrylic ABA triblock copolymer gels Macromolecules (Washington, DC, U. S.) 1999, 32 (21) 7251-7262 10.1021/ma990873h
36. Hertz, H. On the contact of elastic solids J. Reine Angew. Math. 1881, 92, 156-171
37. Shull, K. R.; Chen, W.-L. Fracture Mechanics Studies of Adhesion in Biological Systems Interface Sci. 2000, 8 (1) 95-110 10.1023/A:1008795623603
38. Ding, X.; Vegesna, G. K.; Meng, H.; Winter, A.; Lee, B. P. Nitro-Group Functionalization of Dopamine and its Contribution to the Viscoelastic Properties of Catechol-Containing Nanocomposite Hydrogels Macromol. Chem. Phys. 2015, 216, 1109-1119 10.1002/macp.201500010
39. Yan, J.; Springsteen, G.; Deeter, S.; Wang, B. The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols-it is not as simple as it appears Tetrahedron 2004, 60 (49) 11205-11209 10.1016/j.tet.2004.08.051
40. Springsteen, G.; Wang, B. A detailed examination of boronic acid-diol complexation Tetrahedron 2002, 58 (26) 5291-5300 10.1016/S0040-4020(02)00489-1
41. Bull, S. D.; Davidson, M. G.; van den Elsen, J. M. H.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao, J.; James, T. D. Exploiting the Reversible Covalent Bonding of Boronic Acids: Recognition, Sensing, and Assembly Acc. Chem. Res. 2013, 46 (2) 312-326 10.1021/ar300130w
42. Meng, H.; Li, Y.; Faust, M.; Konst, S.; Lee, B. P. In Hydrogen peroxide generation and biocompatibility of hydrogel-bound mussel adhesive moiety; Acta Biometerialia, 2015, 17, 160 - 169.
43. Kalyanaraman, B.; Felix, C. C.; Sealy, R. C. Semiquinone anion radicals of catechol(amine)s, catechol estrogens, and their metal ion complexes Environ. Health Perspect. 1985, 64, 185-198 10.1289/ehp.8564185
44. Kim, A.; Mujumdar, S.; Siegel, R. Swelling Properties of Hydrogels Containing Phenylboronic Acids Chemosensors 2014, 2 (1) 1-12 10.3390/chemosensors2010001
45. Sever, M. J.; Weisser, J. T.; Monahan, J.; Srinivasan, S.; Wilker, J. J. Metal-Mediated Cross-Linking in the Generation of a Marine-Mussel Adhesive Angew. Chem. 2004, 116 (4) 454-456 10.1002/ange.200352759
46. Lee, B. P.; Narkar, A.; Wilharm, R. Effect of metal ion type on the movement of hydrogel actuator based on catechol-metal ion coordination chemistry Sens. Actuators, B 2016, 227, 248-254 10.1016/j.snb.2015.12.038
47. Chen, G. C. Synthesis and evaluation of aminoborates derived from boric acid and diols for protecting wood against fungal and thermal degradation Wood Fiber Sci. 2008, 40 (2) 248-257
48. Skelton, S.; Bostwick, M.; O'Connor, K.; Konst, S.; Casey, S.; Lee, B. P. Biomimetic adhesive containing nanocomposite hydrogel with enhanced materials properties Soft Matter 2013, 9 (14) 3825-3833 10.1039/c3sm27352k
49. Li, Y.; Meng, H.; Liu, Y.; Narkar, A.; Lee, B. P. Gelatin Microgel Incorporated Poly(ethylene glycol)-Based Bioadhesive with Enhanced Adhesive Property and Bioactivity ACS Appl. Mater. Interfaces 2016, 8 (19) 11980-11989 10.1021/acsami.6b01364
50. Chung, H.; Glass, P.; Pothen, J. M.; Sitti, M.; Washburn, N. R. Enhanced Adhesion of Dopamine Methacrylamide Elastomers via Viscoelasticity Tuning Biomacromolecules 2011, 12 (2) 342-347 10.1021/bm101076e
51. Mian, S. A.; Gao, X.; Nagase, S.; Jang, J. Adsorption of catechol on a wet silica surface: density functional theory study Theor. Chem. Acc. 2011, 130, 333-339 10.1007/s00214-011-0982-0
52. Mian, S. A.; Saha, L. C.; Jang, J.; Wang, L.; Gao, X.; Nagase, S. Density Functional Theory Study of Catechol Adhesion on Silica Surfaces J. Phys. Chem. C 2010, 114, 20793-20800 10.1021/jp1070538