Synthesis of well‐defined star‐shaped poly(ε‐caprolactone)/poly(ethylbene glycol) amphiphilic conetworks by combination of ring opening polymerization and “click” chemistry

Wang, Cui-Wei; Liu, Chao; Zhu, Xiaowei; Yang, Ziying; Sun, Hongfan; Kong, Deling; Yang, Jing

doi:10.1002/pola.27790

Cited by 18 publications

(11 citation statements)

References 50 publications

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“…In another work, CW Wang et al synthesized APCNs based on well‐defined star‐shaped HO poly(caprolactone) (PCL) and HI PEG using ring‐opening polymerization (ROP) and click chemistry. Their studies revealed that synthesized APCNs could be promising materials for sustained release of HO and HI drugs . In PEG‐based hydrogels, mechanical properties, swelling, and consequently, the release behavior of HO and HI components can be influenced by the introduction of polycaprolactone (PCL) as an inexpensive, biocompatible and biodegradable polyester.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of biodegradable multicomponent amphiphilic conetworks with tunable swelling through combination of ring‐opening polymerization and “click” chemistry method as a controlled release formulation for 2,4‐dichlorophenoxyacetic acid herbicide

Dabbaghi

Rahmani

2018

Polymers for Advanced Techs

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Funding informationUniversity of Zanjan Multicomponent (two, three, and four component) amphiphilic conetworks (APCNs) with tunable swelling behaviors were fabricated through the ring opening polymerization and click chemistry utilizing various combinations of azide and alkyne functionalized poly (ethylene glycol) (PEG) and poly (caprolactone) (PCL) precursors. Prepare azido-terminated star-shaped PCL, azido-terminated PEG, alkyne-terminated PEG, and propargylated pentaerythritol were characterized by hydrogen-1 proton nuclear magnetic resonance ( 1 H NMR) and Fourier-transform infrared (FT-IR) spectroscopy.The morphology and thermal behavior of the APCNs were studied by scanning electron microscopy (SEM) and differential scanning calorimetry (DSC). The swelling behavior of APCNs could be manipulated through an establishment of a balance between hydrophilic segments, hydrophobic segments, and cross-linking density.The 2,4-dichlorophenoxyacetic acid (2,4-D) herbicide was entrapped in APCNs as a model agrochemical to study the release profile from APCNs. The obtained results showed that the release of 2,4-D could be controlled by the swelling degree of APCNs. Finally, the biodegradability rates of APCNs were investigated in agricultural soil. The results exhibited that the decrease in the swelling degree led to decreased degradation rate of APCNs. According to obtained results, these APCNs could be used as biomaterials for the controlled release of agrochemicals.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of biodegradable multicomponent amphiphilic conetworks with tunable swelling through combination of ring‐opening polymerization and “click” chemistry method as a controlled release formulation for 2,4‐dichlorophenoxyacetic acid herbicide

Dabbaghi

Rahmani

2018

Polymers for Advanced Techs

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“…Yang and co-workers have synthesized a welldefined star-shaped telechelic hydrophobic PCL with alkyne terminal groups and then coupled it with an azido-terminated PEG via "click chemistry" to prepare well-defined novel amphiphilic PCL/PEG copolymer conetworks (12).…”

Section: Telechelicmentioning

confidence: 99%

Synthesis of an (AB)4-type Star Block Copolymer of L-lactide and Cyclohexene Oxide from a Tetra-Arm Telechelic Macrophotoinitiator

Uyar

Kaya

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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A multi-step reaction process was applied for the synthesis of a novel and well-defined starshaped telechelic macrophotoinitiator with four poly(L-lactide) (PLLA) arms connected to photoinitiating benzoin groups at the chain ends (PLLA-PI)4. To achieve this, 2,2-bis(hydroxymethyl)-1,3-propanediol was used as the initiator which constitutes the core of the star-shaped polymeric scaffold. Benzoin photoreactive end groups of the telechelic (PLLA-PI)4, capable of entering into further polymerization, allowed its use as a polymeric photoinitiator in photoinduced free radical promoted cationic polymerization of cyclohexene oxide (CHO) monomer at =350 nm to produce an (AB)4-type star-shaped block copolymer composed of both esteric L-lactide and etheric cyclohexene oxide chains on each arm, (PLLA-PCHO)4. Structural analysis and characterization of all intermediate and final compounds were done by a series of analytical and spectral methods. Molecular weights of the prepared polymers up to telechelic macrophotoinitiator (PLLA-PI)4 were determined based on 1 H-NMR (Mn H-NMR), GPC (Mn exp) analyses and theoretical calculations (Mn theo) and were found to be in good agreement with each other. Thermal properties and degradations of the prepared polymers were examined by thermogravimetric and differential thermal analyses (TG/DTA). The melting temperature for (PLLA-PCHO)4 was found higher compared to the other homo-type polymers in the literature. The thermogravimetric (TG) analyses showed that incorporation of the thermally stable PCHO block into the structure via photopolymerization improved its stability by increasing its decomposition temperature compared to the prepolymers.

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“…Their study revealed that synthesized hydrogels could be suitable for controlled dual‐release of choline theophyllinate (hydrophilic drug) and 5‐FU (hydrophobic drug). In another work, Wang et al synthesized amphiphilic hydrogels based on alkyne‐terminated six arm star‐shaped PCL and azido‐terminated PEG (N 3 ‐PEG‐N 3 ) using ring‐opening polymerization and click chemistry. Their studies revealed that the swelling and release behavior of the amphiphilic hydrogels is closely related to the composition of hydrophilic and hydrophobic segments.…”

Section: Introductionmentioning

confidence: 99%

Increasing the hydrophilicity of star‐shaped amphiphilic co‐networks by using of PEG and dendritic s‐PCL cross‐linkers

Zare

Dabbaghi

Rahmani

2019

Polymers for Advanced Techs

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New hyperbranched hydrophobic cross‐linkers with peripheral azide groups were synthesized as follows: First, star‐shaped polycaprolactones (sPCL) were synthesized by ring‐opening polymerization of caprolactone in the presence of pentaerythritol and tin (II) octoate. In the next step, sequential acrylation, Micheal addition, tosylation, and azidation by acryloyl chloride, diethanol amine, tosyl chloride, and sodium azide were respectively exploited to synthesize azide‐functionalized hyperbranched star‐shaped polycaprolactones which were named sPCL‐acrylate‐diethanolamine‐azide (sPCL‐AC‐DEA‐N3) and sPCL‐acrylate‐diethanolamine‐acrylate‐diethanolamine‐azide (sPCL‐AC‐DEA‐AC‐N3). All steps were thoroughly characterized by FT‐IR and 1H NMR spectroscopy. The GPC analysis showed that the molecular weight of sPCL increased after two azide functionalizations. Amphiphilic hydrogels based on sPCL‐AC‐DEA‐N3 (Mn = 8130 g/mol) and sPCL‐AC‐DEA‐AC‐N3 (Mn = 10112 g/mol) with linear alkyne‐terminated polyethylene glycols (PEG) (Mn = 2000, 4000, and 6000 g/mol) were synthesized through click coupling between azide and alkyne groups. In both hydrogels, the swelling ratio increased by increasing the molecular weight of PEG. The obtained results showed that the branching of the cross‐linker, significantly affected the swelling ratio of hydrogels. For instance, the swelling ratio of sPCL‐AC‐DEA‐AC‐N3 and PEG‐6000 (Q = 900) was higher than sPCL‐AC‐DEA‐N3 and PEG‐6000 (Q = 600). Despite the high cross‐linking density of sPCL‐AC‐DEA‐AC‐DEA‐N3–based hydrogels, the amount of released theophylline was higher than sPCL‐AC‐DEA‐N3–based hydrogels, due to the high content of PEG in these hydrogels.

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Synthesis of well‐defined star‐shaped poly(ε‐caprolactone)/poly(ethylbene glycol) amphiphilic conetworks by combination of ring opening polymerization and “click” chemistry

Cited by 18 publications

References 50 publications

Synthesis and characterization of biodegradable multicomponent amphiphilic conetworks with tunable swelling through combination of ring‐opening polymerization and “click” chemistry method as a controlled release formulation for 2,4‐dichlorophenoxyacetic acid herbicide

Synthesis and characterization of biodegradable multicomponent amphiphilic conetworks with tunable swelling through combination of ring‐opening polymerization and “click” chemistry method as a controlled release formulation for 2,4‐dichlorophenoxyacetic acid herbicide

Synthesis of an (AB)4-type Star Block Copolymer of L-lactide and Cyclohexene Oxide from a Tetra-Arm Telechelic Macrophotoinitiator

Increasing the hydrophilicity of star‐shaped amphiphilic co‐networks by using of PEG and dendritic s‐PCL cross‐linkers

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