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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Types of Step-Growth Polymers: Polyesters01:20

Types of Step-Growth Polymers: Polyesters

The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Inherently reactive polyHIPE material from dicyclopentadiene.

Sebastijan Kovačič1, Peter Krajnc, Christian Slugovc

  • 1University of Maribor, Faculty of Chemistry and Chemical Engineering, Smetanova 17, SI-2000 Maribor, Slovenia.

Chemical Communications (Cambridge, England)
|September 11, 2010
PubMed
Summary

Stable high internal phase emulsions of dicyclopentadiene were formulated and polymerized to create highly porous monolithic materials. These materials exhibit excellent mechanical properties and offer straightforward functionalization options.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Nanotechnology

Background:

  • High internal phase emulsions (HIPEs) are versatile templates for creating porous materials.
  • Dicyclopentadiene (DCPD) is a cyclic olefin monomer suitable for polymerization.
  • Achieving robust, functionalizable porous materials from HIPEs remains a challenge.

Purpose of the Study:

  • To develop a simple formulation for stable high internal phase emulsions of dicyclopentadiene.
  • To investigate the ring-opening metathesis polymerization (ROMP) of DCPD within HIPE templates.
  • To characterize the resulting porous monolithic materials for mechanical properties and functionalization potential.

Main Methods:

  • Formulation of stable dicyclopentadiene-in-water high internal phase emulsions.
  • Curing of the emulsions using selected ring-opening metathesis polymerization initiators.
  • Characterization of the porous monolithic materials using mechanical testing and surface analysis techniques.

Main Results:

  • A stable high internal phase emulsion of dicyclopentadiene was successfully formulated.
  • Ring-opening metathesis polymerization yielded highly porous monolithic materials.
  • The resulting materials demonstrated paramount mechanical properties.
  • The porous monoliths showed potential for easy functionalization.

Conclusions:

  • A straightforward method for producing highly porous, mechanically robust, and functionalizable monolithic materials from dicyclopentadiene HIPEs has been established.
  • This approach offers a promising route for advanced material applications requiring tailored porosity and surface chemistry.