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Related Concept Videos

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

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

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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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.3K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.6K
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...
3.6K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.4K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.4K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.1K
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...
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Updated: Dec 24, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Prismarene: An Emerging Naphthol-Based Macrocyclic Arene.

Liu-Pan Yang1, Wei Jiang1

  • 1Shenzhen Grubbs Institute, Academy of Advanced Interdisciplinary Studies, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology, Xueyuan Blvd 1088, Shenzhen, 518055, China.

Angewandte Chemie (International Ed. in English)
|April 8, 2020
PubMed
Summary

Researchers developed new naphthol-based macrocyclic arenes, called prismarenes, with efficient synthesis and strong guest-binding capabilities. These compounds show promise for broad applications in supramolecular chemistry.

Keywords:
host-guest chemistrymacrocyclesprismarenessupramolecular chemistry

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Host-Guest Chemistry

Background:

  • Phenol-based macrocyclic arenes are foundational in supramolecular chemistry.
  • Naphthol-based macrocyclic arenes remain largely unexplored.
  • Existing supramolecular chemistry toolboxes lack naphthol-based macrocycles.

Purpose of the Study:

  • To synthesize novel naphthol-based macrocyclic arenes.
  • To investigate the guest-binding properties of these new macrocycles.
  • To establish prismarenes as a viable alternative to phenol-based macrocycles.

Main Methods:

  • Reaction of 2,6-dimethoxynaphthalene with paraformaldehyde.
  • Optimization of reaction conditions for macrocycle synthesis.
  • Assessment of guest-binding ability through experimental methods.

Main Results:

  • Successful synthesis of naphthol-based macrocycles, termed prismarenes.
  • Demonstrated good guest-binding ability of the synthesized prismarenes.
  • Established a straightforward synthetic route for prismarenes.

Conclusions:

  • Prismarenes offer a promising new class of macrocyclic hosts.
  • The simple synthesis and strong binding suggest wide applicability.
  • Naphthol-based macrocycles can significantly expand supramolecular chemistry.