Photoresponsive Hybrid Raspberry‐Like Colloids Based on Cucurbit[8]uril Host–Guest Interactions

Lan, Yang; Karas, Athan; Scherman, Oren A.

doi:10.1002/anie.201309204

Cited by 105 publications

(174 citation statements)

References 42 publications

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“…While there have been examples of microcapsules formed from interfacial polymerization 30,31 or crosslinking 32 of monomers at the interface of a microdroplet, the interfacial assembly of preformed polymeric materials to form multi-layer amphiphilic microcapsules has not yet been demonstrated. Supramolecular host-guest chemistry has been applied in the preparation of various self-assembled structures, including polymers 33,34 , micelles 35 , hydrogels 36,37 , colloids 38 and more recently by our group, microcapsules 39 . In this supramolecular system, CB [8] was exploited to crosslink a naphthol (Np) modified poly(acrylamide) copolymer and methyl viologen (MV) functionalized gold nanoparticles, forming a nanocomposite supramolecular skin around aqueous microdroplets.…”

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confidence: 99%

Interfacial assembly of dendritic microcapsules with host–guest chemistry

et al. 2014

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The self-assembly of nanoscale materials to form hierarchically ordered structures promises new opportunities in drug delivery, as well as magnetic materials and devices. Herein, we report a simple means to promote the self-assembly of two polymers with functional groups at a water-chloroform interface using microfluidic technology. Two polymeric layers can be assembled and disassembled at the droplet interface using the efficiency of cucurbit[8]uril (CB[8]) host-guest supramolecular chemistry. The microcapsules produced are extremely monodisperse in size and can encapsulate target molecules in a robust, well-defined manner. In addition, we exploit a dendritic copolymer architecture to trap a small hydrophilic molecule in the microcapsule skin as cargo. This demonstrates not only the ability to encapsulate small molecules but also the ability to orthogonally store both hydrophilic and hydrophobic cargos within a single microcapsule. The interfacially assembled supramolecular microcapsules can benefit from the diversity of polymeric materials, allowing for fine control over the microcapsule properties.

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confidence: 99%

Interfacial assembly of dendritic microcapsules with host–guest chemistry

et al. 2014

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“…1−4 The shape and structure of the formed clusters depend strongly on the size ratio and volume fractions of the participating particle species. Following this strategy a variety of superstructures have been prepared, including colloidal chains 4 and colloidal crystals.…”

Section: Introductionmentioning

confidence: 99%

pH Reversible Encapsulation of Oppositely Charged Colloids Mediated by Polyelectrolytes

et al. 2017

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We report the first example of reversible encapsulation of micron-sized particles by oppositely charged submicron smaller colloids. The reversibility of this encapsulation process is regulated by pH-responsive poly(acrylic acid) (PAA) present in solution. The competitive adsorption between the small colloids and the poly(acrylic acid) on the surface of the large colloids plays a key role in the encapsulation behavior of the system. pH offers an experimental knob to tune the electrostatic interactions between the two oppositely charged particle species via regulation of the charge density of the poly(acrylic acid). This results in an increased surface coverage of the large colloids by the smaller colloids when decreasing pH. Furthermore, the poly(acrylic acid) also acts as a steric barrier limiting the strength of the attractive forces between the oppositely charged particle species, thereby enabling detachment of the smaller colloids. Finally, based on the pH tunability of the encapsulation behavior and the ability of the small colloids to detach, reversible encapsulation is achieved by cycling pH in the presence of the PAA polyelectrolytes. The role of polyelectrolytes revealed in this work provides a new and facile strategy to control heteroaggregation behavior between oppositely charged colloids, paving the way to prepare sophisticated hierarchical assemblies.

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“…[17][18][19][20][21][22][23] Embedding multiple switches on these PAs via covalent attachment is always a challenging task. [34][35][36] Interestingly, Kim et al reported that when an asymmetric viologen amphiphile is used, such ternary complexation eventually leads to the formation of uniform vesicles. Since the molecules are adhered together through multiple weak interactions, appropriate stimulus can be used to dis-assemble them easily.…”

Section: Introductionmentioning

confidence: 99%

“…[30][31][32][33] Stimuli responsive materials derived from ternary complexes of CB [8] have recently gained significant attention. 36,42,43 A trans-isomer can fit within the available cavity space of MV@CB [8] while the space is not adequate for the cis-isomer. 37 Recently, we have shown that this vesicle formation is a micelle to vesicle transformation and can be achieved with extremely low content of the ternary complex in the system (1% of the total surfactant concentration).…”

Section: Introductionmentioning

confidence: 99%

Reversible deformation–formation of a multistimuli responsive vesicle by a supramolecular peptide amphiphile

et al. 2015

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A systematic study of the ternary complex formation process for aromatic amino acids using ucurbit[8]uril (CB[8]) and a viologen amphiphile shows that the affinity of the amino acid needs to be higher or in a comparable range to that of CB[8] for the amphiphile in order to form the ternary complex. Based on these observations, a supramolecular peptide amphiphile and its corresponding vesicle are prepared using a peptide containing an azobenzene moiety. The azobenzene group at the N-terminus of the peptide served as the second guest for CB[8]. The vesicles obtained from this peptide amphiphile show response to a number of external triggers. The trans-cis isomerization of the azobenzene group upon irradiation with UV-light of 365 nm leads to the breakdown of the ternary complex and eventually to the disruption of the vesicle. The deformation-reformation of the vesicle can be controlled by illuminating the disrupted solution with light of 420 nm as it facilitates the cis-trans isomerization. Thus, the vesicle showed a controlled and reversible response to UV-light with the ability for manipulation of the formation-deformation of the vesicle by the choice of an appropriate wavelength. The vesicle showed response to a stronger guest (1-adamantylamine) for CB[8], which displaces both the guests from the CB[8] cavity and consequently ruptures the vesicle structure. 2,6-Dihydroxynaphthalene acts as a competitive guest and thereby behaves as another external trigger for replacing the peptide from the CB[8] cavity by self-inclusion to form the ternary complex. Henceforth, it allows retaining the vesicle structure and results in the release of the peptide from the vesicle.

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Photoresponsive Hybrid Raspberry‐Like Colloids Based on Cucurbit[8]uril Host–Guest Interactions

Cited by 105 publications

References 42 publications

Interfacial assembly of dendritic microcapsules with host–guest chemistry

Interfacial assembly of dendritic microcapsules with host–guest chemistry

pH Reversible Encapsulation of Oppositely Charged Colloids Mediated by Polyelectrolytes

Reversible deformation–formation of a multistimuli responsive vesicle by a supramolecular peptide amphiphile

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