Fully Oxygen-Tolerant Visible-Light-Induced ATRP of Acrylates in Water: Toward Synthesis of Protein-Polymer Hybrids

Kapil, Kriti; Jazani, Arman Moini; Szczepaniak, Grzegorz; Murata, Hironobu; Olszewski, Mateusz; Matyjaszewski, Krzysztof

doi:10.1021/acs.macromol.2c02537

Cited by 31 publications

(25 citation statements)

References 128 publications

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“…However, UV light has a biocidal effect on biomacromolecules and can cause undesirable side reactions . Alternatively, the dormant polymer chain can be activated by direct electron transfer from an organophotoredox catalyst under visible light irradiation, − but organocatalyzed ATRP (O-ATRP) is mainly limited to methacrylates and organic solvents. − To overcome these limitations, photoredox/copper catalytic systems have been developed, although most of them operate only in the wavelength range of 400 to 520 nm. − …”

Section: Introductionmentioning

confidence: 99%

Red-Light-Driven Atom Transfer Radical Polymerization for High-Throughput Polymer Synthesis in Open Air

Hu,

Szczepaniak,

Lewandowska-Andralojc

et al. 2023

J. Am. Chem. Soc.

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Photoinduced reversible-deactivation radical polymerization (photo-RDRP) techniques offer exceptional control over polymerization, providing access to well-defined polymers and hybrid materials with complex architectures. However, most photo-RDRP methods rely on UV/visible light or photoredox catalysts (PCs), which require complex multistep synthesis. Herein, we present the first example of fully oxygen-tolerant red/ NIR-light-mediated photoinduced atom transfer radical polymerization (photo-ATRP) in a high-throughput manner under biologically relevant conditions. The method uses commercially available methylene blue (MB + ) as the PC and [X−Cu II /TPMA] + (TPMA = tris(2-pyridylmethyl)amine) complex as the deactivator. The mechanistic study revealed that MB + undergoes a reductive quenching cycle in the presence of the TPMA ligand used in excess. The formed semireduced MB (MB • ) sustains polymerization by regenerating the [Cu I /TPMA] + activator and together with [X−Cu II /TPMA] + provides control over the polymerization. This dual catalytic system exhibited excellent oxygen tolerance, enabling polymerizations with high monomer conversions (>90%) in less than 60 min at low volumes (50−250 μL) and high-throughput synthesis of a library of well-defined polymers and DNA−polymer bioconjugates with narrow molecular weight distributions (Đ < 1.30) in an open-air 96-well plate. In addition, the broad absorption spectrum of MB + allowed ATRP to be triggered under UV to NIR irradiation (395−730 nm). This opens avenues for the integration of orthogonal photoinduced reactions. Finally, the MB + /Cu catalysis showed good biocompatibility during polymerization in the presence of cells, which expands the potential applications of this method.

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Section: Introductionmentioning

confidence: 99%

Red-Light-Driven Atom Transfer Radical Polymerization for High-Throughput Polymer Synthesis in Open Air

Hu,

Szczepaniak,

Lewandowska-Andralojc

et al. 2023

J. Am. Chem. Soc.

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“…14,24 Among the various ATRP methods reported, 40 we used the oxygen-tolerant photoinduced ATRP (photo-ATRP) techni-que mediated by eosin Y (EYH 2 ) photocatalyst and a copper complex (X−Cu II /L) under green light irradiation. 41,42 In this green-light-driven ATRP, the excited eosin Y photocatalyst transfers an electron to the X−Cu II /L complex, thereby (re)generating the ATRP activator (Cu I /L) required for polymer growth. Compared to other ATRP methods, this photoredox/Cu-catalyzed ATRP method is particularly advantageous for polymerization from nucleic acid initiators.…”

Section: ■ Introductionmentioning

confidence: 99%

RNA-Polymer Hybrids via Direct and Site-Selective Acylation with the ATRP Initiator and Photoinduced Polymerization

Jeong

Murata

et al. 2023

J. Am. Chem. Soc.

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Combining synthetic polymers with RNA paves the way for creating RNA-based materials with non-canonical functions. We have developed an acylation reagent that allows for direct incorporation of the atom transfer radical polymerization (ATRP) initiator into both short synthetic oligoribonucleotides and natural biomass RNA extracted from torula yeast. The acylation was performed in a quantitative yield. The resulting initiator-functionalized RNAs were used for grafting polymer chains from the RNA by photoinduced ATRP, resulting in RNA-polymer hybrids with narrow molecular weight distributions. The RNA initiator was used for the polymerization of oligo(ethylene oxide) methyl ether methacrylate, poly(ethylene glycol) dimethacrylate, and N-isopropylacrylamide monomers, resulting in RNA bottlebrushes, hydrogels, and stimuli-responsive materials. This approach, readily applicable to both post-synthetic and nature-derived RNA, can be used to engineer the properties of a variety of RNA-based macromolecular hybrids and assemblies providing access to a wide variety of RNA-polymer hybrids.

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“…Due to the small size of their constituent units, nanomaterials have several unique properties, from other materials, such as high specific surface area, excellent electrical/magnetic/thermal properties, good adsorption properties, and so on. Over the past few decades, the green preparation of multifunctional nanocomposites inspired numerous interests in broad research fields. , The nanocomposites composed of noble metal nanoparticles (Ag, Au, Pd, and Pt NPs and so on) and their nanocarriers attract more attention due to their various applications in light energy transformation, electronics, advanced precision equipment, catalysis, − environmental applications, , bioimaging, and bioanalysis, as antibacterial/anticancer agents. − However, the development of economically feasible and green processing technology for high-performance multifunctional noble metal nanocomposites is still challenging.…”

Section: Introductionmentioning

confidence: 99%

Tannin-Assisted Synthesis of Nanocomposites Loaded with Silver Nanoparticles and Their Multifunctional Applications

Xia,

Jiang,

et al. 2023

Biomacromolecules

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Nanocomposites have been widely used in many important areas due to their particular physical/chemical properties; however, just though a simple technology, endowing multiple functions into a single nanomaterial for realizing their multifunctional applications is still a challenge. Here, we report a robust method for the facile synthesis of Ag-based multifunctional nanocomposites via using tannin-coated phenol–formaldehyde resin nanospheres (TA-PFRN) as silver nanoparticle (Ag NP) carriers. The thickness of the tannin coating is readily tuned from 50 to 320 nm by regulating the concentration of tannin added. Under the optimal conditions, the TA-PFRN has a 23.8 wt % of Ag NPs loading capacity with only 17.2 nm Ag NP layers. Consequently, the novel TA-PFRN@Ag nanocomposites possess multiple functions and integrated characteristics. As catalysts, the catalytic efficiency of TA-PFRN@Ag is nearly 6 times higher than that of the PFRN@Ag. As highly effective free radical initiators, TA-PFRN@Ag nanocomposites can trigger ultrafast acrylic acid (AA)/acrylamide (AM) polymerization at room temperature (in only a few minutes). As nano-reinforced fillers, the addition of 0.04 wt % nanocomposites can improve the tensile strength of PVA film from 60 to 153.2 MPa. In addition, the nanocomposites can also serve as antibacterial agents, efficiently inhibiting the growth of Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus); as antiultraviolet agents, the presence of TA-PFRN@Ag nanocomposites endows the film/hydrogel materials excellent ultraviolet (UV) shielding. This work provides a novel strategy for the green synthesis of Ag-based multifunctional nanocomposites that show promising applications in catalysis, nanomaterials, and biomedicine.

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Fully Oxygen-Tolerant Visible-Light-Induced ATRP of Acrylates in Water: Toward Synthesis of Protein-Polymer Hybrids

Cited by 31 publications

References 128 publications

Red-Light-Driven Atom Transfer Radical Polymerization for High-Throughput Polymer Synthesis in Open Air

Red-Light-Driven Atom Transfer Radical Polymerization for High-Throughput Polymer Synthesis in Open Air

RNA-Polymer Hybrids via Direct and Site-Selective Acylation with the ATRP Initiator and Photoinduced Polymerization

Tannin-Assisted Synthesis of Nanocomposites Loaded with Silver Nanoparticles and Their Multifunctional Applications

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