Interfacial structure of a DOPA-inspired adhesive polymer studied by sum frequency generation vibrational spectroscopy

Langmuir

Volumn 29, Issue 22, 2013, Pages 6659-6664

  Leng, Chuan ^a   Liu, Yuwei ^a   Jenkins, Courtney ^b   Meredith, Heather ^b   Wilker, Jonathan J ^b   Chen, Zhan ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADHESIVE POLYMERS; ADHESIVE PROTEINS; BIOLOGICAL SOURCES; DIHYDROXYPHENYLALANINE; INTERFACIAL STRUCTURES; POLYMER INTERFACES; SUM FREQUENCY GENERATION VIBRATIONAL SPECTROSCOPIES; SYNTHETIC ADHESIVES;

ADHESION; HYDROGEN BONDS; MOLLUSCS; PHASE INTERFACES; PHENOLS; POLYMERS; POLYSTYRENES; PROTEINS; STYRENE; VIBRATIONAL SPECTROSCOPY;

CROSSLINKING;

ADHESIVE AGENT; BIOMATERIAL; DOPA; POLY((3,4 DIHYDROXYSTYRENE) CO STYRENE); POLY((3,4-DIHYDROXYSTYRENE)-CO-STYRENE); POLYALLYLAMINE; POLYAMINE; POLYSTYRENE DERIVATIVE; WATER;

AIR; ANIMAL; ARTICLE; BIVALVE; CHEMICAL PHENOMENA; CHEMISTRY; MOLECULAR MIMICRY; SURFACE PROPERTY;

ADHESIVES; AIR; ANIMALS; BIOCOMPATIBLE MATERIALS; BIVALVIA; DIHYDROXYPHENYLALANINE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR MIMICRY; POLYAMINES; POLYSTYRENES; SURFACE PROPERTIES; WATER;

EID: 84878662487     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la4008729     Document Type: Article

References (58)

1. Dougherty, W. J. Sem Observations on the Interfacial Surface of the Cement of the Adult Barnacle, Attached to Natural and Synthetic Adherends Tissue Cell 1990, 22, 463-470
2. Waite, J. H. Evidence for a Repeating 3,4-Dihydroxyphenylalanine- and Hydroxyproline-Containing Decapeptide in the Adhesive Protein of the Mussel, Mytilus Edulis L J. Biol. Chem. 1983, 258, 2911-2915
3. Coyne, K. J.; Qin, X. X.; Waite, J. H. Extensible Collagen in Mussel Byssus: A Natural Block Copolymer Science 1997, 277, 1830-1832
4. Deming, T. J. Mussel Byssus and Biomolecular Materials Curr. Opin. Chem. Biol. 1999, 3, 100-105
5. Danner, E. W.; Kan, Y.; Hammer, M. U.; Israelachvili, J. N.; Waite, J. H. Adhesion of Mussel Foot Protein Mefp-5 to Mica: An Underwater Superglue Biochemistry 2012, 51, 6511-6518
6. 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, 4332-4335
7. Crisp, D. J.; Walker, G.; Young, G. A.; Yule, A. B. Adhesion and Substrate Choice in Mussels and Barnacles J. Colloid Interface Sci. 1985, 104, 40-50
8. Lin, Q.; Gourdon, D.; Sun, C.; Holten-Andersen, N.; Anderson, T. H.; Waite, J. H.; Israelachvili, J. N. Adhesion Mechanisms of the Mussel Foot Proteins Mfp-1 and Mfp-3 Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 3782-3786
9. Yu, M. E.; Hwang, J. Y.; Deming, T. J. Role of l -3,4- Dihydroxyphenylalanine in Mussel Adhesive Proteins J. Am. Chem. Soc. 1999, 121, 5825-5826
10. Monahan, J.; Wilker, J. J. Cross-Linking the Protein Precursor of Marine Mussel Adhesives: Bulk Measurements and Reagents for Curing Langmuir 2004, 20, 3724-3729
11. Suci, P. A.; Geesey, G. G. Influence of Sodium Periodate and Tyrosinase on Binding of Alginate to Adlayers of Mytilus Edulis Foot Protein 1 J. Colloid Interface Sci. 2000, 230, 340-348
12. 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., Int. Ed. 2004, 43, 448-450
13. 3+-Mediated Bridging between DOPA-Containing Protein Films in Water Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 12850-12853
14. Yu, J.; Wei, W.; Danner, E.; Ashley, R. K.; Israelachvili, J. N.; Waite, J. H. Mussel Protein Adhesion Depends on Interprotein Thiol-Mediated Redox Modulation Nat. Chem. Biol. 2011, 7, 588-590
15. Westwood, G.; Horton, T. N.; Wilker, J. J. Simplified Polymer Mimics of Cross-Linking Adhesive Proteins Macromolecules 2007, 40, 3960-3964
16. Yu, M.; Deming, T. J. Synthetic Polypeptide Mimics of Marine Adhesives Macromolecules 1998, 31, 4739-4745
17. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-Inspired Surface Chemistry for Multifunctional Coatings Science 2007, 318, 426-430
18. Holten-Andersen, N.; Harrington, M. J.; Birkedal, H.; Lee, B. P.; Messersmith, P. B.; Lee, K. Y. C.; Waite, J. H. pH-Induced Metal-Ligand Cross-Links Inspired by Mussel Yield Self-Healing Polymer Networks with Near-Covalent Elastic Moduli Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 2651-2655
19. Matos-Pérez, C. R.; White, J. D.; Wilker, J. J. Polymer Composition and Substrate Influences on the Adhesive Bonding of a Biomimetic, Cross-Linking Polymer J. Am. Chem. Soc. 2012, 134, 9498-9505
20. 2 via a Biomimetic Adhesive Group for Sensing and Detection in Complex Media Biosens. Bioelectron. 2010, 25, 2276-2282
21. Statz, A. R.; Meagher, R. J.; Barron, A. E.; Messersmith, P. B. New Peptidomimetic Polymers for Antifouling Surfaces J. Am. Chem. Soc. 2005, 127, 7972-7973
22. Li, G.; Xue, H.; Gao, C.; Zhang, F.; Jiang, S. Nonfouling Polyampholytes from an Ion-Pair Comonomer with Biomimetic Adhesive Groups Macromolecules 2009, 43, 14-16
23. Ye, Q.; Zhou, F.; Liu, W. Bioinspired Catecholic Chemistry for Surface Modification Chem. Soc. Rev. 2011, 40, 4244-4258
24. Wilker, J. J. Biomaterials: Redox and Adhesion on the Rocks Nat. Chem. Biol. 2011, 7, 579-580
25. Lee, H.; Scherer, N. F.; Messersmith, P. B. Single-Molecule Mechanics of Mussel Adhesion Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12999-13003
26. 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
27. Lambert, A. G.; Davies, P. B.; Neivandt, D. J. Implementing the Theory of Sum Frequency Generation Vibrational Spectroscopy: A Tutorial Review Appl. Spectrosc. Rev. 2005, 40, 103-145
28. Zhuang, X. W.; Miranda, P. B.; Kim, D.; Shen, Y. R. Mapping Molecular Orientation and Conformation at Interfaces by Surface Nonlinear Optics Phys. Rev. B 1999, 59, 12632-12640
29. Perry, A.; Neipert, C.; Space, B.; Moore, P. B. Theoretical Modeling of Interface Specific Vibrational Spectroscopy: Methods and Applications to Aqueous Interfaces Chem. Rev. 2006, 106, 1234-1258
30. Chen, Z.; Shen, Y. R.; Somorjai, G. A. Studies of Polymer Surfaces by Sum Frequency Generation Vibrational Spectroscopy Annu. Rev. Phys. Chem. 2002, 53, 437-465
31. Gracias, D. H.; Zhang, D.; Lianos, L.; Ibach, W.; Shen, Y. R.; Somorjai, G. A. A Study of the Glass Transition of Polypropylene Surfaces by Sum-Frequency Vibrational Spectroscopy and Scanning Force Microscopy Chem. Phys. 1999, 245, 277-284
32. Ye, H. K.; Gu, Z. Y.; Gracias, D. H. Kinetics of Ultraviolet and Plasma Surface Modification of Poly(dimethylsiloxane) Probed by Sum Frequency Vibrational Spectroscopy Langmuir 2006, 22, 1863-1868
33. Li, Q. F.; Hua, R.; Cheah, I. J.; Chou, K. C. Surface Structure Relaxation of Poly(methyl methacrylate) J. Phys. Chem. B 2008, 112, 694-697
34. Li, G.; Ye, S.; Morita, S.; Nishida, T.; Osawa, M. Hydrogen Bonding on the Surface of Poly(2-methoxyethyl acrylate) J. Am. Chem. Soc. 2004, 126, 12198-12199
35. (3) Contribution to Sum Frequency Generation Signal Langmuir 2012, 28, 1374-1380
36. Ye, S. J.; Majumdar, P.; Chisholm, B.; Stafslien, S.; Chen, Z. Antifouling and Antimicrobial Mechanism of Tethered Quaternary Ammonium Salts in a Cross-Linked Poly(dimethylsiloxane) Matrix Studied Using Sum Frequency Generation Vibrational Spectroscopy Langmuir 2010, 26, 16455-16462
37. Ye, S. J.; McClelland, A.; Majumdar, P.; Stafslien, S. J.; Daniels, J.; Chisholm, B.; Chen, Z. Detection of Tethered Biocide Moiety Segregation to Silicone Surface Using Sum Frequency Generation Vibrational Spectroscopy Langmuir 2008, 24, 9686-9694
38. Zhang, D.; Ward, R. S.; Shen, Y. R.; Somorjai, G. A. Environment-Induced Surface Structural Changes of a Polymer: An in Situ IR + Visible Sum-Frequency Spectroscopic Study J. Phys. Chem. B 1997, 101, 9060-9064
39. Lachat, V.; Varshney, V.; Dhinojwala, A.; Yeganeh, M. S. Molecular Origin of Solvent Resistance of Polyacrylonitrile Macromolecules 2009, 42, 7103-7107
40. Even, M. A.; Chen, C. Y.; Wang, J.; Chen, Z. Chemical Structures of Liquid Poly(ethylene glycol)s with Different End Groups at Buried Polymer Interfaces Macromolecules 2006, 39, 9396-9401
41. Li, Q.; Hua, R.; Chou, K. C. Electronic and Conformational Properties of the Conjugated Polymer MEH-PPV at a Buried Film/Solid Interface Investigated by Two-Dimensional IR-Visible Sum Frequency Generation J. Phys. Chem. B 2008, 112, 2315-2318
42. Lu, X. L.; Xue, G.; Wang, X. P.; Han, J. L.; Han, X. F.; Hankett, J.; Li, D. W.; Chen, Z. Directly Probing Molecular Ordering at the Buried Polymer/Metal Interface 2: Using p-Polarized Input Beams Macromolecules 2012, 45, 6087-6094
43. Chen, P.; Kung, K. Y.; Shen, Y. R.; Somorjai, G. A. Sum Frequency Generation Spectroscopic Study of CO/Ethylene Coadsorption on the Pt(111) Surface and CO Poisoning of Catalytic Ethylene Hydrogenation Surf. Sci. 2001, 494, 289-297
44. Zhang, C.; Hankett, J.; Chen, Z. Molecular Level Understanding of Adhesion Mechanisms at the Epoxy/Polymer Interfaces ACS Appl. Mater. Interfaces 2012, 4, 3730-3737
45. Santaniello, E.; Manzocchi, A.; Farachi, C. Tetrabutylammonium Periodate-A Selective and Versatile Oxidant for Organic Substrates Synthesis-Stuttgart 1980, 563-565
46. Bagli, J. F. Infrared Spectra of Some Substituted p-Benzoquinones J. Am. Chem. Soc. 1962, 84, 177-180
47. Palmö, K.; Pietilä, L. O.; Mannfors, B.; Karonen, A.; Stenman, F. Raman Scattering from p-Benzoquinone J. Mol. Spectrosc. 1983, 100, 368-376
48. Han, H.; Wu, J.; Avery, C. W.; Mizutani, M.; Jiang, X.; Kamigaito, M.; Chen, Z.; Xi, C.; Kuroda, K. Immobilization of Amphiphilic Polycations by Catechol Functionality for Antimicrobial Coatings Langmuir 2011, 27, 4010-4019
49. Lu, X. L.; Spanninga, S. A.; Kristalyn, C. B.; Chen, Z. Surface Orientation of Phenyl Groups in Poly(sodium 4-styrenesulfonate) and in Poly(sodium 4-styrenesulfonate):Poly(3,4-ethylenedioxythiophene) Mixture Examined by Sum Frequency Generation Vibrational Spectroscopy Langmuir 2010, 26, 14231-14235
50. Chirdon, W. M.; O'Brien, W. J.; Robertson, R. E. Adsorption of Catechol and Comparative Solutes on Hydroxyapatite J. Biomed. Mater. Res., Part B 2003, 66B, 532-538
51. Lio, K.; Minoura, N. Synthesis of Polyallylamine Derivatives with Biguanido Groups J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 2071-2073
52. Rivas, B. L.; Seguel, G. V. Synthesis, Characterization of Poly(allylamine) Chelates with Cu(II), Co(II) and Ni(II) Polym. Bull. 1996, 37, 463-468
53. Loch, C. L.; Ahn, D.; Chen, C.; Wang, J.; Chen, Z. Sum Frequency Generation Studies at Poly(ethylene terephthalate)/Silane Interfaces:Hydrogen Bond Formation and Molecular Conformation Determination Langmuir 2004, 20, 5467-5473
54. Qin, Z.; Buehler, M. Molecular Mechanics of Dihydroxyphenylalanine at a Silica Interface Appl. Phys. Lett. 2012, 101, 083702-4
55. Zhang, Y.; Thomas, Y.; Kim, E.; Payne, G. F. pH- and Voltage-Responsive Chitosan Hydrogel through Covalent Cross-Linking with Catechol J. Phys. Chem. B 2012, 116, 1579-1585
56. Rothschild, K. J.; Roepe, P.; Lugtenburg, J.; Pardoen, J. A. Fourier Transform Infrared Evidence for Schiff Base Alteration in the First Step of the Bacteriorhodopsin Photocycle Biochemistry 1984, 23, 6103-6109
57. Rothschild, K. J.; Marrero, H. Infrared Evidence that the Schiff Base of Bacteriorhodopsin Is Protonated: bR570 and K Intermediates Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 4045-4049
58. Chen, H. Y.; McClelland, A. A.; Chen, Z.; Lahann, J. Solventless Adhesive Bonding Using Reactive Polymer Coatings Anal. Chem. 2008, 80, 4119-4124