Synthesis of water soluble polyrotaxanes by end-capping polypseudo-rotaxanes of γ-CDs with PHEMA-PPO-PEO-PPO-PHEMA using ATRP of MPC

Kong, Tao; Lin, Jing; Ye, Lin; Zhang, Aiying; Feng, Zeng‐guo

doi:10.1039/c5py00674k

Cited by 16 publications

(16 citation statements)

References 43 publications

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“…This is due to the restricting and shielding effects from the inner cavity of γ-CDs against the vibration of the corresponding chemical bond [ 22 ]. This confirmed that the PMPC segments were successfully attached to two ends of the pentablock polymer to convert γ-CD/PMA-PPO-PEO-PPO-PMA PPRs into the PR-based multiblock copolymers [ 14 , 23 ].…”

Section: Resultsmentioning

confidence: 68%

“…In two recent articles [ 13 – 14 ], we reported that attaching PHEMA to two ends of PPO-PEO-PPO via ATRP of HEMA could change its self-assembly process with γ-CDs. Wherein, the γ-CDs were threaded onto and moved over the PHEMA segments to give access to unmatched γ-CD/PHEMA-PPO-PEO-PPO-PHEMA PPRs showing a mixed loose-fit (with PEO) and over-fit (with PHEMA) architecture, instead of the PEO-bent double-chain-stranded tight-fit ones like those of γ-CD/BrPEPBr PPRs [ 15 – 16 ].…”

Section: Resultsmentioning

confidence: 99%

“…It was found that only about one-fifth of the added γ-CDs were left on the PMA-PPO-PEO-PPO-PMA main chains after the second ATRP of MPC in this study. This was most likely due to a relatively smaller cross-sectional area of PMA compared with PHEMA, leading to a lower inclusion complexation stability of PMA-PPO-PEO-PPO-PMA with γ-CDs during the one-pot in situ ATRP of MPC [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

“…It was shown that when self-assembling with PHEMA-PPO-PEO-PPO-PHEMA, γ-CDs could be threaded onto and moved over the 2-hydroxyethyl methacrylate (PHEMA) segments to form a mixed single-chain-stranded loose-fit (PEO) and over-fit (PHEMA) architecture [ 13 ]. Using in situ ATRP, those PPRs were successfully transformed into the same conformational PRs [ 14 ]. Owing to a more flexible or retardant movement of the entrapped γ-CDs along the thinner PEO and thicker PHEMA segments (as compared with PPO or PMAA), respectively, these unmatched PRs possess the potential to be applied as dynamic-responsive materials, carriers for controlled drug release, biosensors and catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

Lin¹,

Kong²,

Ye³

et al. 2015

Beilstein J. Org. Chem.

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SummaryPentablock copolymers PMA-PPO-PEO-PPO-PMA synthesized via atom transfer radical polymerization (ATRP) were self-assembled with varying amounts of γ-CDs to prepare poly(pseudorotaxanes) (PPRs). When the concentration of γ-CDs was lower, the central PEO segment served as a shell of the micelles and was preferentially bent to pass through the γ-CD cavity to construct double-chain-stranded tight-fit PPRs characterized by a channel-like crystal structure. With an increase in the amount of γ-CDs added, they began to accommodate the poly(methyl acrylate) (PMA) segments dissociated from the core of the micelles. When more γ-CDs were threaded and slipped over the segments, the γ-CDs were randomly distributed along the pentablock copolymer chain to generate single-chain-stranded loose-fit PPRs and showed no characteristic channel-like crystal structure. All the self-assembly processes of the pentablock copolymers resulted in the formation of hydrogels. After endcapping via in situ ATRP of 2-methacryloyloxyethyl phosphorylcholine (MPC), these single-chain-stranded loose-fit PPRs were transformed into conformational identical polyrotaxanes (PRs). The structures of the PPRs and PRs were characterized by means of 1H NMR, GPC, 13C CP/MAS NMR, 2D 1H NOESY NMR, FTIR, WXRD, TGA and DSC analyses.

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Section: Resultsmentioning

confidence: 68%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

Lin¹,

Kong²,

Ye³

et al. 2015

Beilstein J. Org. Chem.

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“…There are several CD-based polyrotaxanes known with homo- and block-copolymer axes, mostly based on poly(ethylene oxide), poly(propylene oxide) or their copolymers [ 15 – 21 ], since these polymers can form sufficiently stable complexes with CDs. The application potential of these polyrotaxanes was already investigated in the fields of biomedicine, as drug [ 22 ] or gene [ 23 ] delivery vehicles, or in materials sciences, as slide ring gels [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

Hilschmann

Wenz

Kali

2017

Beilstein J. Org. Chem.

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The aqueous reversible addition fragmentation chain-transfer (RAFT) copolymerization of isoprene and bulky comonomers, an acrylate and an acrylamide in the presence of methylated β-cyclodextrin was employed for the first time to synthesize block-copolyrotaxanes. RAFT polymerizations started from a symmetrical bifunctional trithiocarbonate and gave rise to triblock-copolymers where the outer polyacrylate/polyacrylamide blocks act as stoppers for the cyclodextrin rings threaded onto the inner polyisoprene block. Statistical copolyrotaxanes were synthesized by RAFT polymerization as well. RAFT polymerization conditions allow control of the composition as well as the sequence of the constituents of the polymer backbone which further effects the CD content and the aqueous solubility of the polyrotaxane.

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Synthesis and Characterization of Polyrotaxanes Comprising γ‐CDs and Distal Azide‐Terminated PHEMA Using Propargylamine Monosubstituted β‐CDs as End Stoppers

Gao

Song

et al. 2020

Macro Chemistry & Physics

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To highlight whether γ‐cyclodextrins (CDs) facilitate propargylamine monosubstituted β‐CDs (PA‐β‐CDs) as end stoppers to get threaded onto a distal azide terminated poly(2‐hydroxyethylmethacrylate) (PHEMA) homopolymer (PH‐46‐2N3) to create linear and hyperbranched polyrotaxanes (PRs) via the in situ copper‐catalyzed azide/alkyne cycloaddition (CuAAC), PH‐46‐2N3 is self‐assembled with a varying amount of γ‐CDs in water and then subjected the CuAAC with PA‐β‐CDs to end‐cap the resulting γ‐CD‐PHEMA polypseudorotaxanes (PPRs) into the γ‐CD‐PHEMA PRs. It demonstrates that γ‐CDs cannot promote PA‐β‐CDs to be entrapped on the PHEMA chain most likely due to their different cavity size and molecular framework and linear PRs are always formed with up to 29% γ‐CD coverage ratio along the PHEMA axis thereof.

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Synthesis of water soluble polyrotaxanes by end-capping polypseudo-rotaxanes of γ-CDs with PHEMA-PPO-PEO-PPO-PHEMA using ATRP of MPC

Cited by 16 publications

References 43 publications

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

Synthesis and Characterization of Polyrotaxanes Comprising γ‐CDs and Distal Azide‐Terminated PHEMA Using Propargylamine Monosubstituted β‐CDs as End Stoppers

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