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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
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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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Degradable Polyphosphoramidate via Ring-Opening Metathesis Polymerization.

Yifei Liang1, Hao Sun1,2, Wei Cao1,2

  • 1Department of Chemistry, International Institute for Nanotechnology, Simpson-Querrey Institute, Chemistry of Life Processes Institute, Lurie Cancer Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

ACS Macro Letters
|June 2, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized degradable polyphosphoramidates using ring-opening metathesis polymerization (ROMP). These polymers break down in acidic conditions, offering tunable degradability for advanced materials.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Developing degradable polymers is crucial for sustainable materials and biomedical applications.
  • Ring-opening metathesis polymerization (ROMP) offers a versatile route to synthesize complex polymer architectures.
  • Acid-labile linkages are desirable for controlled degradation in specific environments.

Purpose of the Study:

  • To synthesize a novel degradable polyphosphoramidate via ROMP.
  • To investigate the controlled polymerization of a diazaphosphepine monomer.
  • To explore the copolymerization of this monomer with norbornene derivatives for tunable degradability.

Main Methods:

  • Synthesis of a diazaphosphepine-based cyclic olefin monomer.
  • Ring-opening metathesis polymerization (ROMP) using a Grubbs-type ruthenium catalyst.
  • Acid-catalyzed hydrolysis to study polymer degradation.
  • Random and block copolymerization with phenyl and oligo(ethylene glycol) norbornenes.

Main Results:

  • Achieved controlled ROMP of the diazaphosphepine monomer at low temperatures.
  • Synthesized well-defined polyphosphoramidates with tunable molecular weights.
  • Demonstrated facile degradation in acidic conditions through cleavage of phosphoramidate bonds.
  • Successfully incorporated the diazaphosphepine unit into random and block copolymers with norbornenes.
  • Generated amphiphilic copolymers capable of forming micellar nanoparticles.

Conclusions:

  • A novel degradable polyphosphoramidate was synthesized via controlled ROMP.
  • The phosphoramidate linkage provides an acid-labile point for controlled polymer degradation.
  • Copolymerization allows for the introduction of tunable degradability and amphiphilicity.
  • The developed polymers are promising for applications such as drug delivery systems and nanoparticles.