Preparation of hydrophobic tannins‐inspired polymer materials via low‐ppm ATRP methods

Zaborniak, Izabela; Chmielarz, Paweł; Flejszar, Monika; Surmacz, Karolina; Ostatek, Robert

doi:10.1002/pat.4825

Cited by 11 publications

(13 citation statements)

References 69 publications

(88 reference statements)

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“…The diminution of catalyst complex amount is based on its continuous regeneration due to incorporation of an additional redox cycle using an appropriate reducing agent or external stimulus. These techniques include supplemental activator and reducing agent (SARA) ATRP, activators regeneration by electron transfer (ARGET) ATRP, initiators for continuous activator regeneration (ICAR), or electrochemically mediated ATRP (eATRP), where the ratio of the concentration of activator to deactivator is precisely controlled by electrochemical means . These techniques allow controlled polymerization of various vinyl and acrylic monomers under mild conditions .…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of fluorescent shell functionalized polymer micelles for biomedical application

Ismail

Bryaskova

Georgiev

et al. 2020

Polymers for Advanced Techs

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pH-sensitive polymers can be defined as polyelectrolytes that include in their structure weak acidic or basic groups that either accept or release protons in response to a change in the environmental pH. This work summarizes the design, synthesis, and potential applications of pH-responsive fluorescent copolymers in the biomedical field.This was achieved using atom transfer radical polymerization (ATRP) of tert-butyl acrylate using a CuBr/N,N,N 0 ,N 00 N 00 -pentamethyldiethylenetriamine catalyst system in conjunction with an alkyl bromide as the initiator. Well-defined macroinitiators based on poly(tert-butyl acrylate) with narrow molecular weight distributions were obtained by the addition of an appropriate solvent system in order to create a homogeneous catalytic system. The addition of n-butyl acrylate as a second building block in order to create well-defined poly(tert-butyl acrylate)-b-poly(n-butyl acrylate) block copolymers (PtBA-b-PnBA) followed by chemical modification of the block copolymers and functionalization with an appropriate fluorescent compound are the basis for the preparation of well-defined fluorescent pH-sensitive micelles. Thus, prepared water soluble nanosized pH-sensitive micelles consisting of hydrophobic poly(n-butyl acrylate) core and hydrophilic polyacrylic acid shell decorated with an appropriate fluorescent compound determined their potential applications of these systems in the field of biomedicine as biosensors, controlled drug delivery systems, and so on. In this respect, the cell viability and internalization of the polymer micelles were studied. K E Y W O R D S bioimaging, fluorescent nanosized micelles, personalized theranostic systems, pH-sensitive block copolymers 1 | INTRODUCTION These days, a wide range of compounds being developed are polymers, because of the variety of their chemical and physical properties and the possibility to be tailored towards many applications. In the last two decades, tremendous interest has been shown in polymeric materials that could reversibly or irreversibly change their physical and chemical properties under the influence of external stimuli, eg, pH, temperature, presence of specific ions, light radiation, mechanical forces, magnetic fields, electric fields, and bioactive molecules. 1 Among them, special attention is paid to the well-defined pH block copolymers, which at physiological pH (7.1-7.3) self-assemble into micellar structures and the acidification of the media lead to controlled micelle dissociation and triggered drug release. Several modern techniques can be applied for their synthesis as atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer (RAFT), and stable free radical polymerization (SFRP). 2 These techniques are based on a reversible activation/deactivation cycle of

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of fluorescent shell functionalized polymer micelles for biomedical application

Ismail

Bryaskova

Georgiev

et al. 2020

Polymers for Advanced Techs

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“…Improved hydrophobic, and thus lipophilic properties of troxerutin, resulted from modification by P n BA polymer chains was confirmed by contact angles (Θ) measurements for polar and nonpolar liquid, followed by the calculation of FSE values according to the Owens‐Wendt method (Figure S11 and Table S5). 16,87,88 A significant increase in the value of Θ for polar liquid after incorporation of P n BA chains (compare Θ for water droplets, Table S5) clearly proved the enhancement in hydrophobicity of the troxerutin‐based macromolecule. Two basic components constituting the total value of FSE parameter' dispersive ( γ S d ) and polar ( γ S p ) part.…”

Section: Resultsmentioning

confidence: 86%

“…Each time three droplets were analyzed at 25°C. The geometric analysis of pictures (Camera 13 MP, f/2.2, PDAF) taken for the droplets was conducted by Kropla software to receive the values of contact angles, subsequently used for the calculation of free surface energy (FSE, γ S ) values for troxerutin/polymer coatings according to Owens‐Wendt methods by the software Energia 16 …”

Section: Methodsmentioning

confidence: 99%

“…Flavonoids as polyphenol compounds with functional hydroxyl groups can be easily polymerized with different monomers to enhance their properties 15 . Modification by polymers improves, for example, hydrophobic, 16,17 hydrophilic, 18,19 antifouling, 18,20 antimicrobial, 21 antibacterial 22 properties, pH‐ and temperature‐responsiveness in drug, and gene delivery systems 23‐25 …”

Section: Introductionmentioning

confidence: 99%

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Miniemulsion switchable electrolysis under constant current conditions

Zaborniak

Chmielarz

2020

Polymers for Advanced Techs

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Troxerutin, a naturally occurring flavonoid glycoside, has a variety of beneficial activities characteristic for flavonols, such as strong antioxidant and anti-inflammatory properties. Besides the beneficial effects of troxerutin, limitations such as bioavailability have disrupted its application and prompt scientists to look for effective modification methods. This work presents the synthesis of troxerutin-based macromolecules with lipophilic poly(n-butyl acrylate) (PnBA) star arms via "core-first" procedure in a two-step synthetic route. Troxerutin as a polyphenol structure with ubiquitous reactive hydroxyl groups was for the first time modified with α-bromoisobutyryl bromide to receive an atom transfer radical polymerization (ATRP) initiator with 10 brominated initiation sites. The further step involved the synthesis of novel star-like macromolecules with troxerutin core and PnBA star arms by simplified electrochemically mediated ATRP (seATRP) in an environmentally friendly reaction medium-miniemulsion. Electrolysis under constant current conditions with temporal control was implemented, resulting in well-defined star-like polymers with complete preservation of chain-end functionality after restarting the synthesis. Hydrophobic properties of received troxerutin-based macromolecules were investigated by contact angles (Θ) measurements, followed by the free surface energy (FSE) calculations.

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“…Photos of modified silicon surfaces were taken with a Panasonic DC-FZ82 camera equipped with a LUMIX DC VARIO 1:2.8-5.9/3.58-215 ASPH lens. The obtained contact angles were used to determine the free surface energy of the grafted brushes based on the Owens-Wendt method and van Oss-Good method by Energia software [65,66].…”

Section: Water Contact Angle Measurements (Wca)mentioning

confidence: 99%

Polymer Brushes via Surface-Initiated Electrochemically Mediated ATRP: Role of a Sacrificial Initiator in Polymerization of Acrylates on Silicon Substrates

et al. 2020

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Silicon wafers as semiconductors are essential components of integrated circuits in electronic devices. For this reason, modification of the silicon surface is an important factor in the manufacturing of new hybrid materials applied in micro- and nanoelectronics. Herein, copolymer brushes of hydrophilic poly(2-hydroxyethyl acrylate) (PHEA) and hydrophobic poly(tert-butyl acrylate) (PtBA) were grafted from silicon wafers via simplified electrochemically mediated atom transfer radical polymerization (seATRP) according to a surface-initiated approach. The syntheses of PHEA-b-PtBA copolymers were carried out with diminished catalytic complex concentration (successively 25 and 6 ppm of Cu). In order to optimize the reaction condition, the effect of the addition of a supporting electrolyte was investigated. A controlled increase in PHEA brush thickness was confirmed by atomic force microscopy (AFM). Various other parameters including contact angles and free surface energy (FSE) for the modified silicon wafer were presented. Furthermore, the effect of the presence of a sacrificial initiator in solution on the thickness of the grafted brushes was reported. Successfully fabricated inorganic–organic hybrid nanomaterials show potential application in biomedicine and microelectronics devices, e.g., biosensors.

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Preparation of hydrophobic tannins‐inspired polymer materials via low‐ppm ATRP methods

Cited by 11 publications

References 69 publications

Design and synthesis of fluorescent shell functionalized polymer micelles for biomedical application

Design and synthesis of fluorescent shell functionalized polymer micelles for biomedical application

Miniemulsion switchable electrolysis under constant current conditions

Polymer Brushes via Surface-Initiated Electrochemically Mediated ATRP: Role of a Sacrificial Initiator in Polymerization of Acrylates on Silicon Substrates

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