Catechols as versatile platforms in polymer chemistry
TL;DR: The aim of this paper is to review for the first time the main synthetic approaches developed for the design of novel catechol-based polymer materials and highlight the importance of these groups as versatile platforms for further functionalization of the macromolecular structures, but also surfaces.
About: This article is published in Progress in Polymer Science.The article was published on 2013-01-01. It has received 499 citations till now.
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TL;DR: This free-standing, adhesive, tough, and biocompatible hydrogel may be more convenient for surgical applications than adhesives that involve in situ gelation and extra agents.
Abstract: Adhesive hydrogels are attractive biomaterials for various applications, such as electronic skin, wound dressing, and wearable devices. However, fabricating a hydrogel with both adequate adhesiveness and excellent mechanical properties remains a challenge. Inspired by the adhesion mechanism of mussels, we used a two-step process to develop an adhesive and tough polydopamine-clay-polyacrylamide (PDA-clay-PAM) hydrogel. Dopamine was intercalated into clay nanosheets and limitedly oxidized between the layers, resulting in PDA-intercalated clay nanosheets containing free catechol groups. Acrylamide monomers were then added and in situ polymerized to form the hydrogel. Unlike previous single-use adhesive hydrogels, our hydrogel showed repeatable and durable adhesiveness. It adhered directly on human skin without causing an inflammatory response and was easily removed without causing damage. The adhesiveness of this hydrogel was attributed to the presence of enough free catechol groups in the hydrogel, which we...
676 citations
TL;DR: This Review presents one approach to obtain robust surface modifications of the surface of oxides, namely the covalent attachment of monolayers.
Abstract: The modification of surfaces by the deposition of a robust overlayer provides an excellent handle with which to tune the properties of a bulk substrate to those of interest. Such control over the surface properties becomes increasingly important with the continuing efforts at down-sizing the active components in optoelectronic devices, and the corresponding increase in the surface area/volume ratio. Relevant properties to tune include the degree to which a surface is wetted by water or oil. Analogously, for biosensing applications there is an increasing interest in so-called “romantic surfaces”: surfaces that repel all biological entities, apart from one, to which it binds strongly. Such systems require both long lasting and highly specific tuning of the surface properties. This Review presents one approach to obtain robust surface modifications of the surface of oxides, namely the covalent attachment of monolayers.
670 citations
TL;DR: Direct evidence is provided to support that the PDA surface modification can serve as an effective strategy to form ultrastable coatings on NPs in vivo, which can improve the intracellular delivery capacity and biocompatibility of NPs for biomedical application.
Abstract: Bioinspired polydopamine (PDA) has served as a universal coating to nanoparticles (NPs) for various biomedical applications. However, one remaining critical question is whether the PDA shell on NPs is stable in vivo. In this study, we modified gold nanoparticles (GNPs) with finely controlled PDA nanolayers to form uniform core/shell nanostructures (GNP@PDA). In vitro study showed that the PDA-coated GNPs had low cytotoxicity and could smoothly translocate to cancer cells. Transmission electron microscopy (TEM) analysis demonstrated that the PDA nanoshells were intact within cells after 24 h incubation. Notably, we found the GNP@PDA could partially escape from the endosomes/lysosomes to cytosol and locate close to the nucleus. Furthermore, we observed that the PDA-coated NPs have very different uptake behavior in two important organs of the liver and spleen: GNP@PDA in the liver were mainly uptaken by the Kupffer cells, while the GNP@PDA in the spleen were uptaken by a variety of cells. Importantly, we pro...
510 citations
TL;DR: This review can provide important and timely information regarding mussel-inspired chemistry and will be of great interest for scientists in the chemistry, materials, biology, medicine and interdisciplinary fields.
Abstract: After more than four billion years of evolution, nature has created a large number of fascinating living organisms, which show numerous peculiar structures and wonderful properties. Nature can provide sources of plentiful inspiration for scientists to create various materials and devices with special functions and uses. Since Messersmith proposed the fabrication of multifunctional coatings through mussel-inspired chemistry, this field has attracted considerable attention for its promising and exiciting applications. Polydopamine (PDA), an emerging soft matter, has been demonstrated to be a crucial component in mussel-inspired chemistry. In this review, the recent developments of PDA for mussel-inspired surface modification are summarized and discussed. The biomedical applications of PDA-based materials are also highlighted. We believe that this review can provide important and timely information regarding mussel-inspired chemistry and will be of great interest for scientists in the chemistry, materials, biology, medicine and interdisciplinary fields.
472 citations
TL;DR: This overview of the crosslinking pathways of catechol and derivatives in both natural and synthetic systems is described and will point towards a rational direction for further investigation of the complicated catechols chemistry.
Abstract: Catechols play an important role in many natural systems. They are known to readily interact with both organic (e.g., amino acids) and inorganic (e.g., metal ions, metal oxides) compounds, thereby providing a powerful system for protein curing. Catechol crosslinked protein networks, such as sclerotized cuticle and byssal threads of the mussel, have been shown to exhibit excellent mechanical properties. A lot of effort has been devoted to mimicking the natural proteins using synthetic catechol-functionalized polymers. Despite the success in developing catechol-functionalized materials, the crosslinking chemistry of catechols is still a subject of debate. To develop materials with controlled and superior properties, a clear understanding of the crosslinking mechanism of catechols is of vital importance. This review describes the crosslinking pathways of catechol and derivatives in both natural and synthetic systems. We discuss existing pathways of catechol crosslinking and parameters that affect the catechol chemistry in detail. This overview will point towards a rational direction for further investigation of the complicated catechol chemistry.
467 citations
References
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TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
Abstract: Examination of nature's favorite molecules reveals a striking preference for making carbon-heteroatom bonds over carbon-carbon bonds-surely no surprise given that carbon dioxide is nature's starting material and that most reactions are performed in water. Nucleic acids, proteins, and polysaccharides are condensation polymers of small subunits stitched together by carbon-heteroatom bonds. Even the 35 or so building blocks from which these crucial molecules are made each contain, at most, six contiguous C-C bonds, except for the three aromatic amino acids. Taking our cue from nature's approach, we address here the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach we call "click chemistry". Click chemistry is at once defined, enabled, and constrained by a handful of nearly perfect "spring-loaded" reactions. The stringent criteria for a process to earn click chemistry status are described along with examples of the molecular frameworks that are easily made using this spartan, but powerful, synthetic strategy.
9,069 citations
"Catechols as versatile platforms in..." refers background in this paper
...i) performingCuAAC reactions[266, 267] between either catechol-alkyne[268] or catechol-azide[269] tethered surfaces and appropriate complementary functionalized end-terminated polymers....
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TL;DR: Inspired by the composition of adhesive proteins in mussels, dopamine self-polymerization is used to form thin, surface-adherent polydopamine films onto a wide range of inorganic and organic materials, including noble metals, oxides, polymers, semiconductors, and ceramics.
Abstract: We report a method to form multifunctional polymer coatings through simple dip-coating of objects in an aqueous solution of dopamine. Inspired by the composition of adhesive proteins in mussels, we used dopamine self-polymerization to form thin, surface-adherent polydopamine films onto a wide range of inorganic and organic materials, including noble metals, oxides, polymers, semiconductors, and ceramics. Secondary reactions can be used to create a variety of ad-layers, including self-assembled monolayers through deposition of long-chain molecular building blocks, metal films by electroless metallization, and bioinert and bioactive surfaces via grafting of macromolecules.
8,669 citations
"Catechols as versatile platforms in..." refers background or methods in this paper
...The successfully employed strategies include i)either the oxidative[14] or enzymatic[15] polymerization of functional catechols; ii)the polymerization of monomers bearing catechol groups protected or not (radical polymerization[16] or peptide synthesis[17]);iii) t he controlled/living polymerization of synthetic monomers in the presence of catechol base dinitiators (ATRP,[18]ROMP[19] ....
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...5 (A) where a plateau isobtained after 24 hours.[14] Final polyDp thickness also increases with the polymerization temperature....
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...Thickness evolution of poly(dopamine) (polyDp) coa ting on Si as measured by AFM of patterned surfaces (A), X-ray Photoelectron Spec tros opy (XPS) characterizations of several polyDp coated surfaces (B).[14] The bar gra ph represents the intensity of characteristic substrate signal before (hatched) an after (solid) coating with polyDp....
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...Poly(dopamine) (polyDp) network adapted from Messe r mith et al.[14] OH OH NH2 NH2...
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...These pioneering works have opened up wide possibil ities for the preparation of adherentpoly(catecholamines) based coatings on any ki d of substrates[14, 71]....
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6,927 citations
Book•
19 Mar 1998
TL;DR: Encyclopedia of Chemical Technology The Third Edition of the Encycled encyclopedia of chemical technology as mentioned in this paper is built on the solid foundation of the previous editions of the encyclopedia, which has been updated and updated and many new subjects have been added to reflect changes in chemical technology through the 1970s.
Abstract: Encyclopedia of Chemical Technology The Third Edition of the Encyclopedia of Chemical Technology is built on the solid foundation of the previous editions All of the articles have been rewritten and updated and many new subjects have been added to reflect changes in chemical technology through the 1970s The new edition, however, will be familiar to users of the earlier editions comprehensive, authoritative, accessible, lucid The Encyclopedia remains an indispensable information source for all producers and users of chemical products and materials In the Third Edition, emphasis is given to major present-day topics of concern to all chemists, scientists, and engineers--energy, health, safety, toxicology, and new materials New subjects have been added, especially those related to polymer and plastics technology, fuels and energy, inorganic and solid-state chemistry, composite materials, coating, fermentation and enzymes, pharmaceuticals, surfactant technology, fibers and textiles New features include the use of SI units as well as English units, Chemical Abstracts Service's Registry Numbers, and complete indexing based on automated retrieval from a machine-readable composition system Once again this classic serves as an unrivaled library of information for the chemical and allied industries Some comments about Kirk-Othmer-- The First Edition "No reference library worthy of the name will be without this series It is simply a must for the chemist and chemical engineer" --Chemical and Engineering News The Second Edition "A necessity for any technical library" --Choice
3,513 citations
TL;DR: This work focuses on the characterization of the phytochemical components of Lactide ROP and their role in the regulation of cell reprograming.
Abstract: 23 Stereocontrol of Lactide ROP 6164 231 Isotactic Polylactides 6164 232 Syndiotactic Polylactides 6166 233 Heterotactic Polylactides 6166 3 Anionic Polymerization 6166 4 Nucleophilic Polymerization 6168 41 Mechanistic Considerations 6168 42 Catalysts 6169 421 Enzymes 6169 422 Organocatalysts 6169 43 Stereocontrol of Lactide ROP 6170 44 Depolymerization 6170 5 Cationic Polymerization 6170 6 Conclusion and Perspectives 6171 7 Acknowledgments 6173 8 References and Notes 6173
2,014 citations