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Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive

[Image: see text] Marine organisms such as mussels have mastered the challenges in underwater adhesion by incorporating post-translationally modified amino acids like l-3,4-dihydroxyphenylalanine (DOPA) in adhesive proteins. Here we designed a catechol containing elastomer adhesive to identify the r...

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Autores principales: Kaur, Sukhmanjot, Narayanan, Amal, Dalvi, Siddhesh, Liu, Qianhui, Joy, Abraham, Dhinojwala, Ali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6202650/
https://www.ncbi.nlm.nih.gov/pubmed/30410980
http://dx.doi.org/10.1021/acscentsci.8b00526
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author Kaur, Sukhmanjot
Narayanan, Amal
Dalvi, Siddhesh
Liu, Qianhui
Joy, Abraham
Dhinojwala, Ali
author_facet Kaur, Sukhmanjot
Narayanan, Amal
Dalvi, Siddhesh
Liu, Qianhui
Joy, Abraham
Dhinojwala, Ali
author_sort Kaur, Sukhmanjot
collection PubMed
description [Image: see text] Marine organisms such as mussels have mastered the challenges in underwater adhesion by incorporating post-translationally modified amino acids like l-3,4-dihydroxyphenylalanine (DOPA) in adhesive proteins. Here we designed a catechol containing elastomer adhesive to identify the role of catechol in interfacial adhesion in both dry and wet conditions. To decouple the adhesive contribution of catechol to the overall adhesion, the elastomer was designed to be cross-linked through [2 + 2] photo-cycloaddition of coumarin. The elastomer with catechol moieties displayed a higher adhesion strength than the catechol-protected elastomer. The contact interface was probed using interface-sensitive sum frequency generation spectroscopy to explore the question of whether catechol can displace water and bond with hydrophilic surfaces. The spectroscopy measurements reveal that the maximum binding energy of the catechol and protected-catechol elastomers to sapphire substrate is 7.0 ± 0.1 kJ/(mole of surface O–H), which is equivalent to 0.10 J/m(2). The higher dry and wet adhesion observed in the macroscopic adhesion measurements for the catechol containing elastomer originates from multiple hydrogen bonds of the catechol dihydroxy groups to the surface. In addition, our results show that catechol by itself does not remove the confined interstitial water. In these elastomers, it is the hydrophobic groups that help in partially removing interstitial water. The observation of the synergy between catechol binding and hydrophobicity in enabling the mussel-inspired soft adhesive elastomer to stick underwater provides a framework for designing materials for applications in tissue adhesion and moist-skin wearable electronics.
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spelling pubmed-62026502018-11-08 Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive Kaur, Sukhmanjot Narayanan, Amal Dalvi, Siddhesh Liu, Qianhui Joy, Abraham Dhinojwala, Ali ACS Cent Sci [Image: see text] Marine organisms such as mussels have mastered the challenges in underwater adhesion by incorporating post-translationally modified amino acids like l-3,4-dihydroxyphenylalanine (DOPA) in adhesive proteins. Here we designed a catechol containing elastomer adhesive to identify the role of catechol in interfacial adhesion in both dry and wet conditions. To decouple the adhesive contribution of catechol to the overall adhesion, the elastomer was designed to be cross-linked through [2 + 2] photo-cycloaddition of coumarin. The elastomer with catechol moieties displayed a higher adhesion strength than the catechol-protected elastomer. The contact interface was probed using interface-sensitive sum frequency generation spectroscopy to explore the question of whether catechol can displace water and bond with hydrophilic surfaces. The spectroscopy measurements reveal that the maximum binding energy of the catechol and protected-catechol elastomers to sapphire substrate is 7.0 ± 0.1 kJ/(mole of surface O–H), which is equivalent to 0.10 J/m(2). The higher dry and wet adhesion observed in the macroscopic adhesion measurements for the catechol containing elastomer originates from multiple hydrogen bonds of the catechol dihydroxy groups to the surface. In addition, our results show that catechol by itself does not remove the confined interstitial water. In these elastomers, it is the hydrophobic groups that help in partially removing interstitial water. The observation of the synergy between catechol binding and hydrophobicity in enabling the mussel-inspired soft adhesive elastomer to stick underwater provides a framework for designing materials for applications in tissue adhesion and moist-skin wearable electronics. American Chemical Society 2018-10-09 2018-10-24 /pmc/articles/PMC6202650/ /pubmed/30410980 http://dx.doi.org/10.1021/acscentsci.8b00526 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kaur, Sukhmanjot
Narayanan, Amal
Dalvi, Siddhesh
Liu, Qianhui
Joy, Abraham
Dhinojwala, Ali
Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title_full Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title_fullStr Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title_full_unstemmed Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title_short Direct Observation of the Interplay of Catechol Binding and Polymer Hydrophobicity in a Mussel-Inspired Elastomeric Adhesive
title_sort direct observation of the interplay of catechol binding and polymer hydrophobicity in a mussel-inspired elastomeric adhesive
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6202650/
https://www.ncbi.nlm.nih.gov/pubmed/30410980
http://dx.doi.org/10.1021/acscentsci.8b00526
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