Multi‐Responsive Supramolecular Double Hydrophilic Diblock Copolymer Driven by Host‐Guest Inclusion Complexation between <i>β</i>‐Cyclodextrin and Adamantyl Moieties

Líu, Hao; Zhang, Yanfeng; Hu, Jinming; Li, Changhua; Liu, Shiyong

doi:10.1002/macp.200900279

Cited by 90 publications

(81 citation statements)

References 83 publications

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“…to prove the formation of the desired architectures or to generate multi-stimuli responsive micelles. 11,14,19,25 At 44 C and 50 C the D h of the adamantyl-functionalized poly(DMAAm) does not change significantly as expected for a non-LCST polymer (Fig. S24 †).…”

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confidence: 64%

Miktoarm star polymers via cyclodextrin-driven supramolecular self-assembly

et al. 2012

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We report the formation of a novel class of supramolecular miktoarm star polymers via cyclodextrin host-guest chemistry. Reversible addition-fragmentation chain transfer polymerization from difunctional guest-or alkyne-containing chain transfer agents and copper(I)-catalyzed azide-alkyne cycloaddition leads to hostand guest-containing acrylamido polymers, namely poly(N,Ndimethylacrylamide) and poly(N,N-diethylacrylamide). Subsequently, a supramolecular miktoarm star polymer was formed and characterized via dynamic light scattering and rotating frame nuclear Overhauser effect spectroscopy.The generation of novel macromolecular architectures utilizing the concept of supramolecular chemistry has driven synthetic polymer chemistry significantly in the last few years. 1 Hydrogen bonding, 2,3 metal complexes 4 and inclusion complexes 5 are widely employed in that regard. Cyclodextrins (CDs) are an important class of supramolecular hosts that have the ability to form inclusion complexes. This ability has found manifold utilization in polymer chemistry, e.g. for drug-delivery, 6 to dissolve hydrophobic monomers 7 or to impart water solubility to hydrophobic chain-transfer agents. 8 From the view of macromolecular architectures CDs give the opportunity for the formation of macromolecular architectures that are governed by supramolecular interactions in an aqueous environment. 9 Examples for the utilization of CDs for the formation of complex macromolecular architectures cover a broad range of architectures, e.g. linear diblockcopolymers, 10-14 supramolecular gels, 15,16 star polymers, 17 CDcentered star polymers connected to linear polymers 18,19 or supramolecular grafts for polymer brushes. 20,21 Herein, we report the formation of supramolecular miktoarm star polymers, i.e. star polymers that have arms consisting of more than one polymer type, utilizing CD-and adamantyl-functionalized acrylamido polymers. The precursor polymers were synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization 22,23 -based on a novel two-arm adamantyl bearing trithiocarbonate -of N,N-dimethylacrylamide (DMAAm) and N,Ndiethylacrylamide (DEAAm) and were thoroughly characterized via ESI-MS, NMR and size exclusion chromatography (SEC) in N,Ndimethylacetamide (DMAc). The subsequent formation of the supramolecular complex in water was proven via 2D rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR and is supported by dynamic light scattering (DLS) data.To achieve a mid-chain guest-functionalized polymer a RAFT agent with an adamantyl moiety between two trithiocarbonategroups was synthesized (Schemes 1 and S1 †). The prominent Scheme 1 Synthetic pathway for the supramolecular miktoarm star polymer: poly(DEAAm) is depicted in black, poly(DMAAm) is depicted in red, the CD moiety is depicted orange and the adamantyl group is depicted in dark blue.

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confidence: 64%

Miktoarm star polymers via cyclodextrin-driven supramolecular self-assembly

et al. 2012

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“…A decrease to pH 2 or an increase in temperature led to increase of the solubility of P4VP30 in water and thus to the transformation of the vesicles into micelles. According to this procedure, Liu et al synthesized β‐CD‐PNIPAM and Ad‐functionalized poly(2‐(diethylamino)ethyl methacrylate) (Ad‐PDEA), which formed micelles or vesicles depending on temperature and pH of the aqueous solution . Variation of the host–guest motif was used to selectively disassemble micelles formed by host–guest interactions of β‐CD‐poly(styrene) (CD‐PS) and ferrocene‐poly(ethylene glycol) (Fc‐PEG) .…”

Section: Supramolecular Nanoparticles Mediated By Host–guest Interactmentioning

confidence: 99%

Soft Supramolecular Nanoparticles by Noncovalent and Host–Guest Interactions

Stoffelen

Huskens

2015

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Supramolecular chemistry provides a tool for the formation of highly ordered structures by means of noncovalent interactions. Soft supramolecular nanoparticles are self-assembled nanoassemblies based on small building blocks and stabilized by basic noncovalent interactions, selective host-guest interactions, or a combination of different interaction types. This review provides an overview of the existing approaches for the formation of supramolecular nanoparticles by various types of noncovalent interactions, with a strong focus on host-guest-mediated assemblies. The approaches are ordered based on the nature of the stabilizing supramolecular interaction, while focusing on the aspects that determine the particle structure. Where applicable, the use of these self-assembled nanostructures as vectors in molecular diagnostics and therapeutics is described as well. The stable yet reversible nature of supramolecular interactions and their chemical flexibility offer great prospects for the development of highly engineered nanoparticles which are compatible with the complexity of living systems.

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“…A well‐defined β‐CD‐PNIPAM was synthesized according to a published procedure with a few modifications ().…”

Section: Methodsmentioning

confidence: 99%

Polymer phase transition characteristics coupled with GC‐MS for the determination of phthalate esters

Chen

Xin

et al. 2019

J of Separation Science

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Phthalate esters are easily released from plastics materials and migrate into the soil and water environment, causing serious pollution and posing a great threat to the health of human beings. A novel temperature‐sensitive extractant combined with liquid–liquid microextraction was developed to preconcentrate three phthalates in the water environment. To optimize the extraction efficiency for the three phthalate esters, various parameters, including polymer molecular weight, salt type, salt addition, adsorption time, desorption solvent, desorption volume, and desorption time have been studied. Under optimal conditions, limits of detection and limits of quantification were in the range of 0.007–0.120 and 0.021–0.350 µg/L, respectively. Linearities varied in the range of 5–1000 µg/L, with the correlation coefficients of 0.9867–0.9997. The preconcentration factors were in the range of 25–75. The relative recoveries of the three phthalate esters were in the range of 82.2–105.6% at the spiked levels. The relative standard deviations were in the range of 0.7–9.2% based on triplicate measurements. The results indicate that the temperature‐sensitive material is a good extractant for phthalate esters in water samples.

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Multi‐Responsive Supramolecular Double Hydrophilic Diblock Copolymer Driven by Host‐Guest Inclusion Complexation between β‐Cyclodextrin and Adamantyl Moieties

Cited by 90 publications

References 83 publications

Miktoarm star polymers via cyclodextrin-driven supramolecular self-assembly

Miktoarm star polymers via cyclodextrin-driven supramolecular self-assembly

Soft Supramolecular Nanoparticles by Noncovalent and Host–Guest Interactions

Polymer phase transition characteristics coupled with GC‐MS for the determination of phthalate esters

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