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Related Concept Videos

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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Cyclooctyne End-Functionalized Poly(morpholine-2,5-dione)s.

Johanna Schreiber1,2, Natalie E Göppert1,2, Leanne M Stafast1,2

  • 1Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743, Jena, Germany.

Macromolecular Rapid Communications
|November 29, 2024
PubMed
Summary

This study introduces a novel initiator for controlled polymerization of amino acid-based monomers, creating functional poly(ester amide)s. The cyclooctyne initiator allows for metal-free click chemistry to attach other molecules, enabling customized polymer applications.

Keywords:
click chemistrymorpholine‐2,5‐dionepoly(ester amide)polydepsipeptidering‐opening polymerizationstrain‐promoted azide‐alkyne cycloaddition (SPAAC)

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Ring-opening polymerization (ROP) is a key method for synthesizing polymers.
  • Functional initiators are crucial for controlling polymer architecture and properties.
  • Amino acid-derived monomers offer biocompatibility and tunable properties.

Purpose of the Study:

  • To develop a novel cyclooctyne-functionalized initiator for controlled ROP of morpholine-2,5-diones.
  • To synthesize well-defined poly(ester amide)s with a cyclooctyne moiety at the alpha-end group.
  • To demonstrate the utility of the cyclooctyne group for post-polymerization modification via click chemistry.

Main Methods:

  • Organo-catalyzed ring-opening polymerization (ROP) using a binary system of DBU and TU.
  • Initiation with (1R,8S,9S)-bicyclo-[6.1.0]non-4-yn-9-ylmethanol (BCN-OH).
  • Characterization using 1H NMR, SEC, and MALDI-TOF-MS.
  • Strain-promoted azide-alkyne cycloaddition (SPAAC) for block copolymer synthesis.

Main Results:

  • Controlled ROP of morpholine-2,5-diones initiated by BCN-OH up to 80% monomer conversion.
  • Synthesis of poly(morpholine-2,5-dione)s with low dispersities (≤1.25) and cyclooctyne alpha-end groups.
  • Successful synthesis of a block copolymer by coupling a vitamin A-functionalized poly(2-ethyl-2-oxazoline) to the poly(ester amide) via SPAAC.
  • Confirmation of block copolymer structure using SEC and DOSY NMR.

Conclusions:

  • BCN-OH is an effective initiator for controlled ROP of morpholine-2,5-diones.
  • The cyclooctyne moiety enables versatile, metal-free functionalization of poly(ester amide)s.
  • This approach provides access to a new generation of customizable functional poly(ester amide)s for diverse applications.