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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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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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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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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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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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Alternating Sequence Control for Poly(ester amide)s by Organocatalyzed Ring-Opening Polymerization.

Yang Liang1, Jun-Lin Pan1, Lin-Hao Sun1

  • 1Department of Chemistry, College of Science, Huazhong Agricultural University, Wuhan, 430070, Hubei, China.

Macromolecular Rapid Communications
|October 10, 2019
PubMed
Summary
This summary is machine-generated.

Organocatalyzed ring-opening polymerization enables precise sequence control in polymer synthesis. This study demonstrates the creation of poly(ester amide)s with controlled sequences, opening new avenues in polymer chemistry.

Keywords:
organocatalysispoly(ester amide)ring expansionring-opening polymerizationsequence control

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry

Background:

  • Sequence-controlled polymerization is a key area in advanced polymer chemistry.
  • Achieving precise control over monomer sequence is crucial for tailoring polymer properties.

Purpose of the Study:

  • To demonstrate the feasibility of sequence regulation using organocatalyzed ring-opening polymerization (ROP).
  • To synthesize pre-organized monomers and subsequently polymerize them to create sequence-controlled poly(ester amide)s.

Main Methods:

  • Synthesis of pre-organized monomers using a ring expansion strategy.
  • Organocatalyzed ring-opening polymerization (ROP) employing 1,5,7-triazabicyclo[4.4.0]dec-5-ene as catalyst and benzyl alcohol as initiator.
  • Characterization of resulting poly(ester amide)s (PEAs) using NMR, MALDI-TOF MS, and DSC.

Main Results:

  • Poly(ester amide)s (PEAs) P1-P3 were synthesized with high molecular weights and good yields.
  • NMR and MALDI-TOF MS confirmed the microstructural integrity and sequence control of the polymers.
  • Differential scanning calorimetry indicated that the PEA without methyl branches exhibited crystallinity.

Conclusions:

  • Organocatalyzed ROP is a viable method for achieving sequence control in polymer synthesis.
  • The synthesized PEAs possess well-defined sequences and tunable properties, including crystallinity, thermal stability, wettability, and degradation profiles.