Functionalization of Polysulfones by Click Chemistry

Toiserkani, Hojjat; Yılmaz, Görkem; Yaǧcı, Yusuf; Torun, Lokman

doi:10.1002/macp.201000245

Cited by 53 publications

(54 citation statements)

References 67 publications

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“…[33,34] Many examples of click reactions involving macromolecules were reported. In this laboratory, we have focused on the use of such click reactions for the synthesis of various macromolecular architectures [34][35][36][37][38][39][40][41] and functionalization of polymers [42][43][44][45][46][47], microspheres [48], clays [49,50], and silsesquioxanes [51] with thermal-, photo-, and electro-active groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Küküt

Karal-Yılmaz

Yaǧcı

2012

Designed Monomers and Polymers

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In the present study, a new class of biodegradable graft copolymers of polystyrene (PS) with aliphatic polyester (APE) side chains were synthesized through combination of nitroxide-mediated free radical polymerization (NMRP) and ringopening polymerization (ROP) with copper (I)-catalyzed 'click' chemistry. First, the click component, azido-functional PS (PS-N 3 ) was prepared by copolymerization of styrene and chloromethyl styrene by NMRP followed by the conversion of chlorine groups of the resulting copolymer to azido groups by using NaN 3 in N,N-dimethylformamide. Propargyl functional APEs were prepared independently by ROP of lactic acid and glycolic acid using tin octoate in the presence of propargyl alcohol at 130°C. Finally, PS-N 3 was coupled with the resulting polymers by click chemistry to yield graft copolymers (PS-g-poly (L-lactic-co-glycolic acid) [PLLA] and PS-g-PLLGA, respectively). The intermediates and final graft copolymers were characterized by proton nuclear magnetic resonance ( 1 H NMR) and Fourier transform infrared spectral and gel permeation chromatography analyses. The hydrolytic degradation behavior of the obtained graft copolymers in phosphate buffer saline solution were investigated by the weight loss and molecular weight measurements. It is shown that both copolymers undergo slow hydrolytic degradation, PS-g-PGLLA being relatively faster due to the presence of hydrophilic glycolic acid groups in the structure.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Küküt

Karal-Yılmaz

Yaǧcı

2012

Designed Monomers and Polymers

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“…[21,22] PSUs have also been successfully functionalized with Py by successive chloromethylation, azidation, and click chemistry processes (Scheme 1). [23] Click chemistry has been reported as a promising approach for the construction of various bioconjugates, biomaterials as well as functional bioactive surfaces. [24] In a previous work, [23] we demonstrated that PSUs can be successfully post-functionalized by using click chemistry on the example of fluorescent Py molecule.…”

Section: Introductionmentioning

confidence: 99%

“…[23] Click chemistry has been reported as a promising approach for the construction of various bioconjugates, biomaterials as well as functional bioactive surfaces. [24] In a previous work, [23] we demonstrated that PSUs can be successfully post-functionalized by using click chemistry on the example of fluorescent Py molecule. It was considered that incorporation of such molecules might bring remarkable fluorescence regulated behavior when subjected to irradiation which makes them useful candidates for various applications in biomolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Polysulfone/Pyrene Membranes: A New Microwell Assay Platform for Bioapplications

Karadag

Yılmaz

Toiserkani

et al. 2011

Macromolecular Bioscience

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The use of PSU-Py prepared by click chemistry as a platform in membrane-bottom microwell plates for oxidase and hydrolase/oxidase-based enzyme assays is studied. For the GOx assay, the postulated fluorescence mechanism is based on the consumption of glucose by dissolved oxygen and GOx in the microwell plates covered with the PSU-Py membrane. For the AG-GOx assay, maltose is used as AG substrate and hydrolyzed to glucose which is then oxidized by the GOx activity. It is shown that the PSU-Py membrane acts as a fluorescence indicator of the enzymatic reactions, and both GOx and AG/GOx enzyme assays are successfully applied for glucose, maltose and acorbose analysis in the range 0.125-2.0 × 10(-3) M glucose, 0.05-0.5 × 10(-3) M maltose, and 0.0125-0.1 mg · mL(-1) acorbose, respectively.

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“…[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] The copper-catalyzed click reactions, Diels-Alder reactions, and thiol-ene reactions are such click reactions with very high yields and nearly no by-product formation. Recently, the ketene chemistry is also announced as a promising route for the modification of macromolecular structures with significant yields.…”

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confidence: 99%