Catechol- and ketone-containing multifunctional bottlebrush polymers for oxime ligation and hydrogel formation

Slegeris, Rimantas; Ondrusek, Brian A.; Chung, Hoyong

doi:10.1039/c7py01112a

Cited by 22 publications

(19 citation statements)

References 62 publications

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“…Although, more recently other natural and synthetic phenolic ligands have been used with a variety of metal ions. Other self-assembled structures include nanoparticles, micelles, [125] vesicles, [126] and brushes, [127] which can be produced by controlling the assembly conditions. Moreover, metal ions can be used to assemble phenolic-coated particles into superstructures.…”

Section: Particlesmentioning

confidence: 99%

“…This design allowed for the presence of free catechols after gel formation, and the catechols could slow the drug release rate from the network when compared to individual micelles. [127] Other macrostructures can be achieved using copolymers of poly(N-(4-aminophenyl) methacrylamide-copolyethylene glycol monomethyl ether methacrylate), where postpolymerization functionalization through a Schiff base formation from 3,4-dihydroxybenzaldehyde allowed for assembly with cosolvent mixtures of Fe III or Cu II into either solid particles or vesicles (Figure 8b,c). [126] Very recently, fiber-like self-assembled materials were obtained from TA and poly(2-ethyl-2-oxazoline) using a thin film templating approach followed by rearrangement with acidic buffer.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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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: Particlesmentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

Phenolic Building Blocks for the Assembly of Functional Materials

et al. 2018

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“…GA wurde traditionell als ditoper Ligand für die MOF‐Synthese verwendet, obwohl in jüngster Zeit andere natürliche und synthetische phenolische Liganden mit einer Vielzahl von Metallionen verwendet werden. Weitere selbstorganisierte Strukturen sind Nanopartikel, Micellen, Vesikel und Bürsten, die durch Steuerung der Assemblierungsbedingungen hergestellt werden können. Darüber hinaus können Metallionen verwendet werden, um phenolbeschichtete Partikel zu Superstrukturen zusammenzufügen .…”

Section: Partikelunclassified

“…In einer eleganten Synthese eines norbornenhaltigen Makromonomers mit einem anhängenden silylgeschützten Catechol wurden “Flaschenbürsten”‐Strukturen synthetisiert und über Ketofunktionen vernetzt. Diese Konstruktion ermöglichte die Anwesenheit von freien Catecholen nach der Gelbildung, und die Catechole konnten die Freisetzungsrate der Medikamente aus dem Netzwerk im Vergleich zu individuellen Micellen verringern . Andere Makrostrukturen können mit Copolymeren aus Poly( N ‐(4‐Aminophenyl)methacrylamid‐ co ‐polyethylenglykolmonomethylethermethacrylat) erreicht werden, wobei die Funktionalisierung nach der Polymerisation durch Bildung einer Schiffschen Base mit 3,4‐Dihydroxybenzaldehyd die Assemblierung in Lösungsmittelgemischen mit Fe III oder Cu II zu festen Partikeln oder Vesikeln erlaubt (Abbildung b,c) .…”

Section: Partikelunclassified

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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“…Particularly important is the adhesion at the interface between the polymeric chains and several different substrates to be then released (where and when needed) upon action of an external stimulus. On a molecular level, this translates in the presence of reversible bonds between the polymeric network and such “loading.” For example, the catechol chemistry (Figure 1) can actually be employed to ensure adhesion of the polymeric chains to several different moieties while crosslinking the network in an irreversible way [15].…”

Section: Introductionmentioning

confidence: 99%

Hydrogels Based on Dynamic Covalent and Non Covalent Bonds: A Chemistry Perspective

Picchioni

Muljana

2018

Gels

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Hydrogels based on reversible covalent bonds represent an attractive topic for research at both academic and industrial level. While the concept of reversible covalent bonds dates back a few decades, novel developments continue to appear in the general research area of gels and especially hydrogels. The reversible character of the bonds, when translated at the general level of the polymeric network, allows reversible interaction with substrates as well as responsiveness to variety of external stimuli (e.g., self-healing). These represent crucial characteristics in applications such as drug delivery and, more generally, in the biomedical world. Furthermore, the several possible choices that can be made in terms of reversible interactions generate an almost endless number of possibilities in terms of final product structure and properties. In the present work, we aim at reviewing the latest developments in this field (i.e., the last five years) by focusing on the chemistry of the systems at hand. As such, this should allow molecular designers to develop a toolbox for the synthesis of new systems with tailored properties for a given application.

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Catechol- and ketone-containing multifunctional bottlebrush polymers for oxime ligation and hydrogel formation

Abstract: We report the synthesis of a highly-functional macromonomer, and subsequent crosslinkable poly(ethylene glycol) (PEG)-based bottlebrush polymers prepared via graft-through ring-opening metathesis polymerization (ROMP).

Cited by 22 publications

References 62 publications

Phenolic Building Blocks for the Assembly of Functional Materials

Phenolic Building Blocks for the Assembly of Functional Materials

Phenolische Bausteine für die Assemblierung von Funktionsmaterialien

Hydrogels Based on Dynamic Covalent and Non Covalent Bonds: A Chemistry Perspective

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