Stabilization and Functionalization of Polymer Multilayers and Capsules via Thiol−Ene Click Chemistry

Connal, Luke A.; Kinnane, Cameron R.; Zelikin, Alexander N.; Caruso, Frank

doi:10.1021/cm803011w

Cited by 110 publications

(93 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…150 Since that time, photochemical reticulation has been extensively studied using diazo, 151154 benzophenone, 155157 vinylbenzyl, 158,159 or vinylphenol 160,161 groups as well as the thiolene reaction. 162 A large number of different systems using strategy (i) have been developed. Of the most popular, heat treatment was introduced in 1999 by Harris et al for covalently reticulation of PAHpoly(acrylic acid) (PAA) multilayers.…”

Section: History Of Layer-by-layermentioning

confidence: 99%

Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution

et al. 2013

View full text Add to dashboard Cite

Materials fabrication with nanoscale structural precision based on bottom-up-type self-assembly has become more important in various current disciplines in chemistry including materials chemistry, organic chemistry, physical chemistry, analytical chemistry, biochemistry, colloid and surface chemistry, and supramolecular chemistry. Although the design of new materials based on nanoscale self-assembly is anticipated as a key concept, preparing complete three-dimensional structures at nanoscale precision remains a difficult target using current technologies. Rather, dimension-reduced approaches such as layering of two-dimensional nanostructures into precisely controlled lamellar nanomaterials are currently achievable. In particular, layer-by-layer (LbL) assembly is known as a highly versatile method for fabrication of controlled layered structures from various kinds of component materials using very simple, inexpensive, and rapid procedures. Therefore, fabrication of multilayer films through the LbL deposition process has attracted growing interest from various research communities. The high versatility and flexibility of LbL assembly is continuously creating new concepts, new materials, new procedures, and new applications. In this highlight review, we focus on nanoarchitectonics by LbL assembly. After an initial introduction on the invention and a brief history of the LbL assembly technique, innovations and the evolution of the technique are described based mainly on recent examples, which are categorized into two sections: (i) developments in methodology (technical, material, and phenomenological aspects with expansion of concept) and (ii) progress in applications (physical, chemical/biochemical, and biomedical applications).

show abstract

Section: History Of Layer-by-layermentioning

confidence: 99%

Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution

et al. 2013

View full text Add to dashboard Cite

show abstract

“…6,7 The subsequent dissolution of the CaCO 3 core yields, then, the substrate-loaded microcapsules. Different methods to assemble the shells of the microcapsules were reported, [8][9][10][11][12][13][14] and a variety of external stimuli to degrade the microcapsules and release the loads were discussed. These included the thermal degradation of the microcapsules by the light-induced excitation of plasmonic nanoparticles entrapped in the microcapsules, [15][16][17] by the local heating of magnetic nanoparticle-loaded microcapsules using an alternate magnetic field, 18 and by the mechanical ultrasound or microwave agitation of the microcapsules.…”

Section: Introductionmentioning

confidence: 99%

Light-Responsive and pH-Responsive DNA Microcapsules for Controlled Release of Loads

et al. 2016

View full text Add to dashboard Cite

A method to assemble light-responsive or pH-responsive microcapsules loaded with different loads (tetramethylrhodamine-modified dextran, TMR-D; microperoxidase-11, MP-11; CdSe/ZnS quantum dots; or doxorubicin-modified dextran, DOX-D) is described. The method is based on the layer-by-layer deposition of sequence-specific nucleic acids on poly(allylamine hydrochloride)-functionalized CaCO3 core microparticles, loaded with the different loads, that after the dissolution of the core particles with EDTA yields the stimuli-responsive microcapsules that include the respective loads. The light-responsive microcapsules are composed of photocleavable o-nitrobenzyl-phosphate-modified DNA shells, and the pH-responsive microcapsules are made of a cytosine-rich layer cross-linked by nucleic acid bridges. Irradiating the o-nitrobenzyl phosphate-functionalized microcapsules, λ = 365 nm, or subjecting the pH-responsive microcapsules to pH = 5.0, results in the cleavage of the microcapsule shells and the release of the loads. Preliminary studies address the cytotoxicity of the DOX-D-loaded microcapsules toward MDA-MB-231 breast cancer cells and normal MCF-10A breast epithelial cells. Selective cytotoxicity of the DOX-D-loaded microcapsules toward cancer cells is demonstrated.

show abstract

“…More recently, thiol-ene chemistry has been introduced as a new click reaction [44] and successfully used for bioconjugated polymers, [45,46] modification of polymers [47][48][49][50][51][52] and surfaces, [53][54][55] synthesis of star polymers, [56] dendrimers, [57] and disaccharides. [58] Thiol-ene reactions can be induced photochemically or thermally at ambient temperature in the presence of oxygen without undesirable side reactions such as sulfenyl radical coupling.…”

Section: Introductionmentioning

confidence: 99%

Influence of Type of Initiation on Thiol–Ene “Click” Chemistry

Uygun

Taşdelen

Yaǧcı

2009

Macro Chemistry & Physics

226

161

View full text Add to dashboard Cite

Thermally and photochemically initiated thiol–ene click reactions using thiol‐ and allyl‐ end functionalized linear polystyrenes with various enes (allyl bromide, methyl acrylate, and methyl methacrylate) and thiol (3‐mercaptopropionic acid) have been investigated. Allyl‐ and thiol‐end‐capped polystyrenes with controlled molecular weight and low polydispersity were prepared by atom transfer radical polymerization (ATRP) of styrene using functional initiator and end group modification approaches, respectively. Thiol–ene reactions can be initiated by both cleavage type photoinitiators such as (2,4,6‐trimethylbenzoyl)diphenylphosphine oxide (TMDPO) and 2,2‐dimethoxy‐2‐phenyl acetophenone (DMPA) and H‐abstraction type photoinitiators such as benzophenone (BP), thioxanthone (TX), camphorquinone (CQ), and classical thermal initiator, 2,2′‐azobis(isobutyronitrile) (AIBN) at 80 °C. The kinetics of the reactions was monitored online with a real time ATR‐FTIR monitoring system and the conversions were determined by 1H NMR spectroscopy. A comparison of click efficiencies of the studied initiator systems was performed. Compare to the thermal initiators and H‐abstraction type photoinitiators, cleavage type photoinitiators were found to induce thiol–ene click reactions with higher efficiency.magnified image

show abstract

Stabilization and Functionalization of Polymer Multilayers and Capsules via Thiol−Ene Click Chemistry

Cited by 110 publications

References 31 publications

Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution

Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution

Light-Responsive and pH-Responsive DNA Microcapsules for Controlled Release of Loads

Influence of Type of Initiation on Thiol–Ene “Click” Chemistry

Contact Info

Product

Resources

About