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Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...

Aromatic Hydrocarbon Cations: Structural Overview

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...

Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Aromatic Hydrocarbon Anions: Structural Overview

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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...

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Related Experiment Video

Updated: Jan 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

A 2,3-dialkoxynaphthalene-based naphthocage.

Song-Bo Lu¹, Hongxin Chai¹, Jas S Ward²

¹Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Xueyuan Blvd 1088, Shenzhen, 518055, China. jiangw@sustech.edu.cn.

Chemical Communications (Cambridge, England)

|December 21, 2019

Summary

This summary is machine-generated.

A novel 2,3-dialkoxynaphthalene-based naphthocage selectively binds small organic cations. This discovery enables the self-sorting of similar naphthocages and guests, advancing molecular recognition capabilities.

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Naphthocages are cage-like molecules with potential applications in molecular recognition.
The binding properties of naphthocages are influenced by their structural isomers, such as 2,3- and 2,6-dialkoxynaphthalene derivatives.
Selective binding of small organic cations remains a challenge in supramolecular chemistry.

Purpose of the Study:

To synthesize a novel 2,3-dialkoxynaphthalene-based naphthocage.
To investigate the cation-binding preferences of this new naphthocage.
To explore the potential for self-sorting of different naphthocage isomers with structurally similar guests.

Main Methods:

Synthesis of the 2,3-dialkoxynaphthalene-based naphthocage.
Cation-binding studies using various small organic cations.
Self-sorting experiments with tetramethylammonium and tetraethylammonium cations.

Main Results:

Successful synthesis of the 2,3-dialkoxynaphthalene-based naphthocage.
The naphthocage exhibits a preference for binding small organic cations.
A low-symmetry conformation of the 2,3-naphthocage facilitates selective cation binding, contrasting with 2,6-isomers.
Effective self-sorting of 2,3- and 2,6-naphthocages with tetramethylammonium and tetraethylammonium was achieved.

Conclusions:

The 2,3-dialkoxynaphthalene-based naphthocage offers unique binding properties due to its conformation.
This naphthocage represents a new tool for selective molecular recognition of organic cations.
The demonstrated self-sorting capability highlights the potential for complex supramolecular assemblies.