Primary Amine-Functionalized Silicon Surfaces via Click Chemistry with α-Alkynyl-Functionalized Poly(2-aminoethyl methacrylate)

Alidedeoglu, Alp H.; Harris, Christopher A.; Martínez-Castro, Nemesio; York, Adam W.; McCormick, Charles L.; Morgan, Sarah E.

doi:10.1021/bk-2010-1053.ch006

Cited by 11 publications

(10 citation statements)

References 59 publications

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“…40 The difference in the calculated weight percent of poly(AEM) and poly(AEMA) grafted CNCs could be due to the challenge in executing controlled polymerization of these monomers, whereby unprotected amine containing monomers are known to undergo unwanted side reactions. 42 In both techniques, trace amounts of sulfur were observed due to the sulfate ester groups, with peaks at 167 eV in XPS. We observed a general increase in the percentage of carbon both by XPS and elemental analysis, due to the presence of polymer grafts on the CNCs' surface.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cationic Poly(2-aminoethylmethacrylate) and Poly(N-(2-aminoethylmethacrylamide) Modified Cellulose Nanocrystals: Synthesis, Characterization, and Cytotoxicity

et al. 2014

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Section: ■ Results and Discussionmentioning

confidence: 99%

Cationic Poly(2-aminoethylmethacrylate) and Poly(N-(2-aminoethylmethacrylamide) Modified Cellulose Nanocrystals: Synthesis, Characterization, and Cytotoxicity

et al. 2014

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“…53 Numerous amine-containing monomers with RAFT polymerization conditions required an acidic buffer to prevent CTA aminolysis. 64 Thang et al demonstrated that trithiocarbonate CTAs exhibited increased hydrolytic stability compared to the corresponding dithioesters. 65 In addition, Moad and Mc-Cormick discovered that trithiocarbonate CTAs effectively controlled more reactive monomers such as acrylamides and methacrylamides.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Controlled Radical Polymerization of 4-Vinylimidazole

et al. 2012

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We report the unprecedented controlled radical polymerization of 4-vinylimidazole (4VIM). Reversible addition–fragmentation chain transfer (RAFT) of 4VIM in glacial acetic acid afforded homopolymers with well-defined molecular weights and narrow polydispersity indices (PDIs). The polymerizations in acetic acid mediated with 4-cyano-4-(ethylsulfanylthiocarbonylsulfanyl)pentanoic acid (CEP) displayed linear pseudo-first-order kinetics and linear molecular weight growth with monomer conversion. Systematic variation of numerous polymerization parameters included solvent composition, initiator concentration, monomer concentration, and the calculated degree of polymerization. Aqueous size exclusion chromatography (SEC) confirmed linear molecular weight growth to number-average molecular weights (M n) of 65 000 g/mol with low PDIs (<1.20). Subsequent monomer addition confirmed the presence of the trithiocarbonate functionality at the chain ends, which provided further evidence of controlled polymerization conditions. Polymerizations in traditional aqueous RAFT solvents (acidic buffers) failed to achieve controlled molecular weight growth. Effectively controlling 4VIM homopolymerizations enables the design of amphoteric block copolymers for emerging applications including nucleic acid delivery and electroactive membranes.

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“…The aRAFT polymerization of PGalEAm exhibits an initialization period of 50 min, while that of PGlcEAm is 100 min. Similar initialization periods in aqueous RAFT polymerizations have been reported previously by our team, including Alidedeoglu et al 32 38 investigated the initialization period observed in the RAFT polymerization of styrene with the chain transfer agent cyanoisopropyl dithiobenzoate via in situ 1 H NMR. It was found that the time taken by the chain transfer agents to react with a single monomer unit is the reason for the observed delay of polymerization.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Aqueous RAFT Synthesis of Glycopolymers for Determination of Saccharide Structure and Concentration Effects on Amyloid β Aggregation

Das¹,

Dean²,

Fogel³

et al. 2017

Biomacromolecules

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GM1 ganglioside is known to promote amyloid-β (Aβ) peptide aggregation in Alzheimer’s disease. The roles of the individual saccharides and their distribution in this process are not understood. Acrylamide-based glycomonomers with either β-d-glucose or β-d-galactose pendant groups were synthesized to mimic the stereochemistry of saccharides present in GM1 and characterized via 1H NMR and electrospray ionization mass spectrometry. Glycopolymers of different molecular weights were synthesized by aqueous reversible addition–fragmentation chain transfer (aRAFT) polymerization and characterized by NMR and GPC. The polymers were used as models to investigate the effects of molecular weight and saccharide unit type on Aβ aggregation via thioflavin-T fluorescence and PAGE. High molecular weight (~350 DP) glucose-containing glycopolymers had a profound effect on Aβ aggregation, promoting formation of soluble oligomers of Aβ and limiting fibril production, while the other glycopolymers and negative control had little effect on the Aβ propagation process.

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Primary Amine-Functionalized Silicon Surfaces via Click Chemistry with α-Alkynyl-Functionalized Poly(2-aminoethyl methacrylate)

Cited by 11 publications

References 59 publications

Cationic Poly(2-aminoethylmethacrylate) and Poly(N-(2-aminoethylmethacrylamide) Modified Cellulose Nanocrystals: Synthesis, Characterization, and Cytotoxicity

Cationic Poly(2-aminoethylmethacrylate) and Poly(N-(2-aminoethylmethacrylamide) Modified Cellulose Nanocrystals: Synthesis, Characterization, and Cytotoxicity

Controlled Radical Polymerization of 4-Vinylimidazole

Aqueous RAFT Synthesis of Glycopolymers for Determination of Saccharide Structure and Concentration Effects on Amyloid β Aggregation

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