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Related Concept Videos

Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
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Anionic Chain-Growth Polymerization: Mechanism01:04

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by π-π Stacking Interactions
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Net anionic poly(β-amino ester)s: synthesis, pH-dependent behavior, and complexation with cationic cargo.

Mara K Kuenen1, Alexa M Cuomo1, Vincent P Gray1

  • 1Department of Chemical Engineering, University of Virginia, Charlottesville, VA, 22903, USA.

Polymer Chemistry
|October 16, 2023
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Researchers created anionic poly(β-amino ester)s (PBAEs) for drug delivery by inverting their charge. These new anionic PBAEs offer tunable degradation and complexation, enabling controlled release of cationic therapeutics.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biomedical Engineering

Background:

  • Poly(β-amino ester)s (PBAEs) are typically cationic and hydrolytically labile, useful for complexing anionic compounds like nucleic acids.
  • Existing PBAEs have limitations in delivering cationic therapeutics due to their inherent positive charge.

Purpose of the Study:

  • To engineer fully-degradable polyelectrolyte complexes and delivery vehicles for cationic therapeutics by inverting the net charge of PBAEs.
  • To synthesize net-anionic PBAEs using alkyne-functionalized monomers and anionic thiol-containing molecules.

Main Methods:

  • Synthesized alkyne-functionalized PBAEs and installed anionic thiols via radical thiol-yne reaction.
  • Developed preparative size exclusion chromatography for purification, avoiding polymer hydrolysis.
  • Characterized net-anionic PBAEs using 1H NMR spectroscopy and assessed their complexation with a cationic peptide.

Main Results:

  • Successfully synthesized net-anionic PBAEs with tunable solution behavior dependent on pH.
  • Demonstrated hydrophobic content-dependent hydrolysis and degradation in aqueous environments.
  • Showcased complexation with cationic peptide (GR)10, with time-dependent disintegration correlating with polymer hydrolysis.

Conclusions:

  • Established a novel synthesis and purification route for previously inaccessible net-anionic PBAEs.
  • Anionic PBAEs offer tunable solution and degradation properties for controlled complexation and release.
  • These anionic PBAEs present new opportunities for degradable polyelectrolyte complexes and cationic therapeutic delivery systems.