Functionalization of Poly(oxindole biphenylylene) membranes by photoinduced thiol-yne click chemistry

Arslan, Mustafa; Pulido, Bruno A.; Nunes, Suzana Pereira; Yaǧcı, Yusuf

doi:10.1016/j.memsci.2019.117673

Cited by 12 publications

(5 citation statements)

References 49 publications

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“…“Click” reactions show great potential for use in membrane technology due to the simplicity, the high yields of the reaction conditions, and the resulting chemical stability of the polymers formed. Most studies using “click” chemistry are focused on minor precursor modifications either before − or after , the layer formation. However, thus far no study has used the powerful and high yielding “click” reactions to form distinct membrane selective layers.…”

Section: Introductionmentioning

confidence: 99%

New Method toward a Robust Covalently Attached Cross-Linked Nanofiltration Membrane

Kyriakou

Merlet

Willott

et al. 2020

ACS Appl. Mater. Interfaces

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As nanofiltration applications increase in diversity, there is a need for new fabrication methods to prepare chemically and thermally stable membranes with high retention performance. In this work, thio-bromo “click” chemistry was adapted for the fabrication of a robust covalently attached and ultrathin nanofiltration membrane. The selective layer was formed on a pre-functionalized porous ceramic surface via a novel, liquid–vapor interfacial polymerization method. Compared to the most common conventional interfacial polymerization procedure, no harmful solvents and a minimal amount of reagents were used. The properties of the membrane selective layer and its free-standing equivalent were characterized by complementary physicochemical analysis. The stability of the thin selective layer was established in water, ethanol, non-polar solvents, and up to 150 °C. The potential as a nanofiltration membrane was confirmed through solvent permeability tests (water, ethanol, hexane, and toluene), PEG-in-water molecular weight cut-off measurements (≈700 g mol –1 ), and dye retention measurements.

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Section: Introductionmentioning

confidence: 99%

New Method toward a Robust Covalently Attached Cross-Linked Nanofiltration Membrane

Kyriakou

Merlet

Willott

et al. 2020

ACS Appl. Mater. Interfaces

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“…The rigid contorted structure of the bulky side oxindole prevents efficient packing in the solid-state and provides these polymers with improved solubility without any decrease in thermal stability. Furthermore, isatin-based polymers can be further chemically modified by the insertion of highly reactive allyl- and propargyl groups , or by facilitating grafting. , …”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, isatinbased polymers can be further chemically modified by the insertion of highly reactive allyl-and propargyl groups 36,38 or by facilitating grafting. 37,39 To the best of our knowledge, the polymers based on isatin and diimides containing ortho-positioned hydroxyl groups have not been reported, whereas those based on 2,2,2trifluorocetophenone have been reported but obtained by a classical polyimide synthesis involving a three-step-synthesized diamine monomer (1-bis[4-(4-aminophenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane). 40 The attempts to prepare aromatic PIs by one-step synthesis using such catalyst−solvent systems as salicylic acid 41 and ionic liquids (1-ethyl-3-methylimidazolium acetate) are also worthy of note.…”

Section: Resultsmentioning

confidence: 99%

“…The methodology has been applied to synthesize polymers (e.g., poly(aryl piperidinium, poly(oxindolebiphenylylene), etc.) for the preparation of gas separation membranes, , fuel cells, − and ultra- and nanofiltration. − Inspired by these promising results we have extended the application of superacid-catalyzed polyhydroxyalkylation for the synthesis of wholly aromatic PIs.…”

Section: Introductionmentioning

confidence: 99%

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One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

et al. 2021

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Efficient and ambient synthesis of aromatic polyimides (PIs) from readily available starting materials remains a very challenging task in polymer chemistry. Herein, we report for the first time a robust, one-step synthesis of organo-soluble functional aromatic PIs. Room temperature, metal-free, superacid (TFSA)-catalyzed step polymerization of aryl-terminated diimides with carbonyl compounds (2,2,2-trifluoroacetophenone and indoline-2,3-dione (isatin)) afforded 14 high-molecular-weight, linear, film-forming PIs. The effect of structural variation of the dianhydride segment, the amount of catalyst, and monomer concentration were studied. The PIs were obtained in quantitative yields, with high thermal stabilities up to 525 °C and 55% weight residue at 800 °C under an inert atmosphere and number-average molecular weights (M n) in a range of 51–195 kg mol–1. Well-controlled proportions of the functional phenolic hydroxyl groups (at the ortho-position to the imide ring) and diaryloxindole reactive sites were introduced into macromolecules during polyimide syntheses, while pendent allyl and propargyl groups were formed by the chemical postpolymerization reactions. Subsequent modifications of the reactive sites using click-chemistry can afford multifunctional polymers with tunable properties. The thermal postpolymerization modification of polyhydroxyimides converts them into polybenzoxazoles (so-called thermally rearranged polymers).

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“…Recently, biomimetic mussel-inspired adhesion chemistry has exhibited broad applicability to various substrates with low surface energy and the potential for post-functional modification, providing a platform for membrane modification. − Polydopamine (PD) as a functional platform can react with primary amino or thiol terminal compounds or polymers to achieve immobilization through the Schiff base reaction or Michael addition reaction. − In addition, efficient click chemistry shows unique potential for the functional modification of membranes. − Therefore, the preparation of anti-biofouling MF membranes based on the active–passive strategy combined with modern biomimetic adhesion chemistry and click chemistry would be an efficient and feasible strategy.…”

Section: Introductionmentioning

confidence: 99%

Integration of a Hydrophilic Hyperbranched Polymer and a Quaternary Ammonium Compound to Mitigate Membrane Biofouling

Yang

Zhu

Lin

et al. 2022

ACS Appl. Polym. Mater.

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Membrane biofouling, adhesion of microorganisms on the surface and the subsequent formation of a biofilm, remains a persistent and inevitable issue, which results in a dramatic reduction of permeability and lifespan. Constructing a membrane with active bacteria-killing and passive anti-adhesion properties is still a challenge to mitigate membrane biofouling. Herein, an active–passive anti-biofouling membrane was originally fabricated by integration of hydrophilic hyperbranched poly(N-acryloylmorpholine) (HPA) and the dimethylaminoethyl acrylate–dodecylammonium bromide (DD) quaternary ammonium compound. Inspired by modern dopamine biomimetic adhesion chemistry, thiolated HPA was first immobilized on the polydopamine (PD)-modified poly(vinylidene fluoride) membrane surface through Michael addition, followed by conjugation of DD via a thiol–ene click reaction. The membrane surface changes of the chemical structure, hydrophilicity, and zeta potential proved that bacteria-killing DD and the anti-adhesion HPA layer were successively conjugated. The initial contact angle of the M-PD/HPA/DD membrane was reduced from 120.5° for the pure membrane to 52.3°. Furthermore, the water flux of the M-PD/HPA/DD membrane increased from 318.9 L m–2 h–1 (0.02 MPa) for the pure membrane to 854.4 L m–2 h–1. In addition, the M-PD/HPA/DD membrane exhibited excellent active bacteria-killing property with inhibition rates of ∼90% for Escherichia coli and ∼95% for Staphylococcus aureus, respectively. Meanwhile, in the filtration of artificial bacteria wastewater, the M-PD/HPA/DD membrane showed a higher water flux recovery rate of 86.9% than 43.3% for the pure membrane, indicating an excellent anti-biofouling property. Therefore, this molecular-level design approach for the modification of the membrane surface could significantly enhance permeability and mitigate membrane biofouling, which provides a promising dimension for the preparation of the anti-biofouling membrane.

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Functionalization of Poly(oxindole biphenylylene) membranes by photoinduced thiol-yne click chemistry

Cited by 12 publications

References 49 publications

New Method toward a Robust Covalently Attached Cross-Linked Nanofiltration Membrane

New Method toward a Robust Covalently Attached Cross-Linked Nanofiltration Membrane

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

Integration of a Hydrophilic Hyperbranched Polymer and a Quaternary Ammonium Compound to Mitigate Membrane Biofouling

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