Hydrophobized plant polyphenols: self-assembly and promising antibacterial, adhesive, and anticorrosion coatings

Payra, Debabrata; Naito, Masanobu; Fujii, Yoshihisa; Nagao, Yuki

doi:10.1039/c5cc07090b

Cited by 52 publications

(42 citation statements)

References 38 publications

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“…Traditionally, phenolic-based materials have been used as pigments, antioxidants, photographic developers, and inks. [70] However, in recent times, their broad range chemical properties and functions have made them useful precursors for constructing a range of smart, advanced materials including stimuli-responsive materials, [192,193] antibacterial and chemical-resistant materials, [194,195] superstructures, [128] unique polymeric materials, [196] DNA origami-based materials, [197] and other nanosystems. [198,199] Moreover, natural polyphenols have recently been shown to provide enhanced blood circulation after complexation with proteins.…”

Section: Applicationsmentioning

confidence: 99%

Phenolic Building Blocks for the Assembly of Functional Materials

et al. 2018

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Phenolic materials have long been known for their use in inks, wood coatings, and leather tanning. However, recently there has been a renewed interest in engineering advanced materials from phenolic building blocks. The intrinsic properties of phenolic compounds, such as metal chelation, hydrogen bonding, pH responsiveness, redox potentials, radical scavenging, polymerization, and light absorbance, have made them a distinct class of structural motifs for the synthesis of functional materials. Materials prepared from phenolic compounds often retain many of these useful properties with synergistic effects in applications ranging from catalysis to biomedicine. The present review provides an overview of the diverse functional materials that can be prepared from phenolic building blocks, bridging the various fields currently studying and using phenolic compounds. Natural and synthetic phenolic compounds are first discussed, followed by the assembly of functional materials. The engineered phenolic materials are grouped under three broad categories: thin films (e.g., metal-phenolic networks and polydopamine); particles (e.g., metal-organic frameworks and superstructures); and bulk materials (e.g., gels). Applications of phenolic-based materials are then presented, focusing mainly on mechanical (e.g., adhesives), biological (e.g., drug delivery), and environmental and energy (e.g., separation and catalysis) applications. Several examples of their emerging applications are also included. Finally, potential routes for the continued integration of disparate fields using phenolic building blocks and fundamental questions still requiring investigation are highlighted, and an outlook of the field is provided.

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Section: Applicationsmentioning

confidence: 99%

Phenolic Building Blocks for the Assembly of Functional Materials

et al. 2018

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“…1,2 It consists of a center glucose molecule with all five hydroxyl moieties esterified with two gallic acid (3,4,5-trihydroxybenzoic acid) molecules. The trihydroxylphenyl groups play an important role in binding a variety of substrates through chemical and physical interactions, [3][4][5][6][7][8][9][10][11][12][13] which are similar to the adhesion mechanism of 3,4-dihydroxyphenylalanine (DOPA)-enriched adhesive proteins of blue mussels. 14 TA can be deposited onto various organic and inorganic substrates because of its inherent affinity towards surfaces.…”

Section: Introductionmentioning

confidence: 99%

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Pranantyo

Neoh

et al. 2016

ACS Sustainable Chem. Eng.

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Inspired by tea stains, a new surface anchor, maleimido-containing tannic acid (TAMA), was developed to introduce the maleimido functionality onto the stainless steel (SS) surfaces. The feasibility of maleimido groups to serve as anchoring sites for surface functionalization via Michael addition was explored in a model experiment using thiol-containing 1H,1H,2H,2H-perfluorodecanethiol. The surface conjugation efficiency of TAMA with the thiol-containing compounds via Michael addition was also compared to that of the surface with tannic acid (TA) only. Water-soluble thiolated carboxymethyl chitosan (CMCSSH) was then grafted on the SS surface pre-anchored with TAMA via solution immersion and spin coating.The deposition of CMCSSH was characterized by contact angle measurement, surface zeta potential, and X-ray photoelectron spectroscopy (XPS). The antifouling efficacy of the CMCSSH coatings was evaluated by protein adsorption and bacterial adhesion. The cytotoxic effect of the CMCSSH coatings on mammalian cells was evaluated using the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with 3T3 fibroblasts.

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“…In addition, the partial substitution of hydrophilic hydroxyl groups by hydrophobic alkyl bromide moieties may facilitate the layer‐by‐layer deposition due to the adoption of an amphiphilic TA‐Br molecular. Consequently, the hydrophobic alkyl bromides tend to become positioned at one side of the TA‐Br molecule and the hydrophilic hydroxyl groups tend to become localized at the other side, rather than undergoing the random aggregation that is observed with pristine TA molecules . Based on the following two measurements, it could be concluded that the surface of glass was completely covered by a TA layer.…”

Section: Resultsmentioning

confidence: 92%

“…WILEYONLINELIBRARY.COM/APP the hydrophobic alkyl bromides tend to become positioned at one side of the TA-Br molecule and the hydrophilic hydroxyl groups tend to become localized at the other side, rather than undergoing the random aggregation that is observed with pristine TA molecules. 36 Based on the following two measurements, it could be concluded that the surface of glass was completely covered by a TA layer. First, silica elements could not be detected via XPS due to the depth limitation of 10 nm for XPS measurements, while the number ratio of C/O/Br atoms was 60.52/38.3/1.17 (Table I), which was similar to that revealed via 1 H NMR characterization.…”

Section: Articlementioning

confidence: 93%

Highly transparent thermoresponsive surfaces based on tea‐stain‐inspired chemistry

Dong

Yuan

et al. 2018

J of Applied Polymer Sci

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A highly transparent thermoresponsive surface that could switch its wettability at different temperatures was constructed via tea‐stain‐inspired chemistry. The pristine tannic acid was modified by alkyl bromide with a substitution degree of 1.7 alkyl bromide units per tannic acid molecule. A coating of the alkyl bromine modified tannic acid with a thickness of 22 ± 3 nm was deposited onto the surface of glass via auto‐oxidation. A poly(N‐isopropylacrylamide) (PNIPAAm) brush was grafted from the alkyl bromide initiator via surface initiation atom transfer radical polymerization with a polymer grafting density of 8.6 × 10−3 mg/cm2. Due to the low thickness of the tannic acid and PNIPAAm coating, the transparency of this thermoresponsive surface remained constant at 94.3% even when the temperature was changed from 20 to 40 °C, but the water contact angle of this surface increased rapidly when the temperature was elevated from 25 to 35 °C. Due to the inevitable hydrolysis and deprotonation, this tea‐stain‐inspired chemistry‐based coating was stable in aqueous solution with a pH of 7 or isopropanol for soaking times of up to 24 h. The coating reported here may have various potential applications such as surfaces for cell culture media, food storage, or self‐cleaning materials. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46694.

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Hydrophobized plant polyphenols: self-assembly and promising antibacterial, adhesive, and anticorrosion coatings

Cited by 52 publications

References 38 publications

Phenolic Building Blocks for the Assembly of Functional Materials

Phenolic Building Blocks for the Assembly of Functional Materials

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Highly transparent thermoresponsive surfaces based on tea‐stain‐inspired chemistry

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