Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Mu, Youbing; Wu, Xiao‐Feng; Pei, Danfeng; Wu, Zelin; Zhang, Chen; Zhou, Dongshan; Wan, Xin

doi:10.1021/acsbiomaterials.7b00673

Cited by 48 publications

(46 citation statements)

References 34 publications

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“…They did, however, find a correlation between the adhesion force and the ratio of cationic to hydrophobic residues in the remainder of the peptide. This is in agreement with the work of Mu et al [27], who investigated the influence of polymer backbone polarity on catechol adhesion by introducing a catecholic moiety at ≈20% of the monomers in polystyrene, poly(acrylate-co-acrylamide), polyacrylamide, and poly( N -vinylpyrrolidone), and comparing wet (seawater) and dry adhesion using a lap-shear test (Figure 3d) on aluminum, glass, and polytetraflourethylen substrates. They found that the bonding strength increased with increasing polarity of the backbone polymer, demonstrating the importance of the chemical environment for catechol adhesion.…”

Section: Catechol Chemistrysupporting

confidence: 90%

“…The diverse chemistry of catechols is summarized in Scheme 1. Strong, yet reversible, and very pH-dependent coordination bonds establish strong adhesion to inorganic surfaces (metals and metal oxides) [1,24,25,26,27] (Scheme 1f,g) as well as hard metal ions in solution [6,28,29,30,31,32,33,34] (Scheme 1c). Similarly, catechols can participate in boronate species (Scheme 1d) that are reversible, even if they possess a high degree of covalency [35,36,37,38].…”

Section: Catechol Chemistrymentioning

confidence: 99%

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Bioinspired Metal–Polyphenol Materials: Self-Healing and Beyond

2019

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The blue mussel incorporates the polyphenolic amino acid l-3,4-dihydroxyphenylalanine (DOPA) to achieve self-healing, pH-responsiveness, and impressive underwater adhesion in the byssus threads that ensure the survival of the animal. This is achieved by a pH-dependent and versatile reaction chemistry of polyphenols, including both physical interactions as well as reversible and irreversible chemical bonding. With a short introduction to the biological background, we here review the latest advances in the development of smart materials based on the metal-chelating capabilities of polyphenols. We focus on new ways of utilizing the polyphenolic properties, including studies on the modifications of the nearby chemical environment (on and near the polyphenolic moiety) and on the incorporation of polyphenols into untraditional materials.

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Section: Catechol Chemistrysupporting

confidence: 90%

Section: Catechol Chemistrymentioning

confidence: 99%

Bioinspired Metal–Polyphenol Materials: Self-Healing and Beyond

2019

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“…[ 17 ] White and Wilker [ 18 ] and Joy and co‐workers [ 19,20 ] incorporated monomers with electrostatic charges or aliphatic pendants into CFPs, achieving underwater bonding strength of 0.4 MPa on aluminum and 0.65 MPa on glass, respectively. By adjusting the polarity [ 21 ] or the hydrophilicity [ 22 ] of CFP backbones, Wan et al reported improved bonding strength of 1.13 and 1.33 MPa on glass substrates. Waite and co‐workers constructed complex coacervates by incorporating polycation with catechol‐functionalized polyanion, which also achieved robust underwater adhesion.…”

Section: Methodsmentioning

confidence: 99%

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Sha

Zhang

et al. 2020

Macromol. Rapid Commun.

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crosslinking [2,3] and metal ion chelation processes. [4,5] Thus, up to now, great efforts have been made to incorporate DOPA or catechol groups in a broad range of designed polymers to get mussel-inspired adhesives, which showed good bonding performances both at dry and underwater conditions. These polymers were generally named as "catecholfunctionalized polymers" (CFPs).Up to now, notable accomplishments have been achieved by using CFPs for high performance adhesion at atmospheric environment. Yu and Deming and co-workers reported the synthesis of DOPA-containing copolypeptides, exhibiting a bonding strength of 4.0 MPa on aluminum. [6] Wilker et al. synthesized poly[(3,4-dihydroxystyrene)-co-styrene] via anionic polymerization method, which achieved a bonding strength of 11 MPa on aluminum by using CaCO 3 particles as reinforcing materials. [7] Subsequently, they also incorporated the CFPs with poly(lactic acid) [8][9][10] or pendant oligo(ethylene glycol) moieties [4] to produce biodegradable/biocompatible adhesives with good dry-state bonding strength. Wan et al. synthesized catechol-functionalized poly(vinyl alcohol) via esterification reactions [11] and acetal formation reactions, [12] exhibiting bonding strengths of 4.0 MPa on glass and 14.9 MPa on stainless steel, respectively. Kaneko et al. synthesized a hyperbranched CFP via thermal polycondensation reaction between 3,4-dihydroxycinnamic acid and 4-hydroxycinnamic acid, which showed a bonding strength of ≈10 MPa on steel. [13] Then, they also prepared a similar hyperbranched polymer system with the bonding strength on steel up to 15 MPa. [14] However, despite great progress, the bonding strength of most reported CFPs on metal substrates is smaller than 15 MPa. Recently, Messersmith and co-workers [15] and Detrembleur and co-workers [16] separately reported the synthesis of catechol-functionalized polybenzoxazines and polyhydroxyurethanes, which were used to prepare thermoset adhesive materials with excellent bonding strength of 20.5 MPa on aluminum and 22.1 MPa on stainless steel, respectively. To our knowledge, these two polymers represent the best adhesive materials among CFPs for dry-state adhesion on metal Marine mussels have the ability to cling to various surfaces at wet or underwater conditions, which inspires the research of catechol-functionalized polymers (CFPs) to develop high-performance adhesive materials. However, these polymeric adhesives generally face the problems of complex synthetic route, and it is still high challenging to prepare CFPs with excellent adhesive performance both at dry and underwater conditions. Herein, a mussel-inspired alternating copolymer, poly(dopamine-alt-2,2-bis(4-glycidyloxyphenyl) propane) (P (DA-a-BGOP)), is synthesized in one step by using commercially available monomers through epoxy-amino click chemistry. The incorporation of polar groups and rigid bisphenol A structures into the polymer backbone enhances the cohesion energy of polymer matrix. The alternating polymer structure endows the polymers with high...

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“…So zeigte eine Studie über die Polarität der Hauptkette eines synthetischen Polymers mit Catechol‐Einheiten eine zusätzliche Komplikationsquelle, da die Polarität spezifische Eigenschaften des Polymers, z. B. die Unterwasseradhäsion, verändert . Andere Untersuchungen an redoxaktiven catecholhaltigen Polymeren ergaben, dass die Veränderung des catecholhaltigen Monomers sowie des Comonomers das Leistungsverhalten bei der elektrochemischen Energiespeicherung beeinflussen kann .…”

Section: Phenolische Bausteineunclassified

Phenolische Bausteine für die Assemblierung von Funktionsmaterialien

et al. 2018

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Phenolische Materialien sind seit langem für ihre Verwendung in Farbtinten, in Holzbeschichtungen und zur Ledergerbung bekannt. In letzter Zeit ist jedoch ein wachsendes Interesse an der Entwicklung moderner Werkstoffe aus phenolischen Bausteinen zu verzeichnen. Die intrinsischen Eigenschaften von phenolischen Verbindungen, wie Metallchelat‐Bildung, Wasserstoffbrücken, pH‐Ansprechverhalten, Redoxpotentiale, Radikalfänger, Polymerisation und Lichtabsorption, haben sie zu einer eigenständigen Klasse von Strukturelementen für die Synthese von funktionellen Materialien gemacht. Aus Phenolverbindungen hergestellte Materialien behalten viele ihrer nützlichen Eigenschaften, oft mit synergistischen Effekten bei Anwendungen, die von der Katalyse bis zur Biomedizin reichen. Dieser Aufsatz gibt einen Überblick über die verschiedenen funktionellen Materialien, die aus natürlichen und synthetischen phenolischen Bausteinen hergestellt werden können, und über ihre Anwendungen.

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Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Cited by 48 publications

References 34 publications

Bioinspired Metal–Polyphenol Materials: Self-Healing and Beyond

Bioinspired Metal–Polyphenol Materials: Self-Healing and Beyond

Mussel‐Inspired Alternating Copolymer as a High‐Performance Adhesive Material Both at Dry and Under‐Seawater Conditions

Phenolische Bausteine für die Assemblierung von Funktionsmaterialien

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