Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.9K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.8K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

13.9K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
13.9K
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

8.0K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
8.0K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

10.2K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
10.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.4K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Oxidative Porphyrinoid Metamorphosis of Fourfold N-Confused [32]Octaphyrin Bis-Metal Complex to Doubly Linked 10-Oxacorrole Metal Complex Dimer.

Angewandte Chemie (International ed. in English)·2026
Same author

Fixing Pillar[5]Arene-Based Rotaxanes Into Epoxy Networks to Produce Toughened Epoxy Resins.

Angewandte Chemie (International ed. in English)·2026
Same author

Evaluation of Tissue Adequacy by Computed Tomography-Guided Needle Biopsy for Comprehensive Genomic Profiling Following Chemotherapy.

Cureus·2026
Same author

Large Exchange Bias Effect in Geometrically Frustrated Spin Glass Through High-Density Coherent Chemical Interfaces.

Advanced materials (Deerfield Beach, Fla.)·2026
Same author

Solid-solution surface alloying of Cu nanocubes with platinum-group metals: pathway switching and catalyst stabilization in CO<sub>2</sub> reduction.

Chemical science·2026
Same author

Comparison of the intraoperative intra-aneurysm pressure gradients among seven off-the-shelf endovascular aneurysm repair devices.

Surgery today·2026

Related Experiment Video

Updated: Feb 1, 2026

Chemical Dimerization-Induced Protein Condensates on Telomeres
08:52

Chemical Dimerization-Induced Protein Condensates on Telomeres

Published on: April 12, 2021

3.7K

Aromatic and Antiaromatic Cyclophane-type Hexaphyrin Dimers.

Akito Nakai1, Tomoki Yoneda1, Shin-Ichiro Ishida1

  • 1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.

Chemistry, an Asian Journal
|December 15, 2018
PubMed
Summary

Researchers synthesized a cyclophane-type dimer using [28]hexaphyrins, which are rectangular and antiaromatic. X-ray analysis confirmed the structure, revealing no electronic interaction between the segments, thus no three-dimensional aromaticity.

Keywords:
aromaticitycyclophaneexpanded porphyrinhexaphyrinolefin metathesis

More Related Videos

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.6K
Visualization of ATP Synthase Dimers in Mitochondria by Electron Cryo-tomography
10:39

Visualization of ATP Synthase Dimers in Mitochondria by Electron Cryo-tomography

Published on: September 14, 2014

31.0K

Related Experiment Videos

Last Updated: Feb 1, 2026

Chemical Dimerization-Induced Protein Condensates on Telomeres
08:52

Chemical Dimerization-Induced Protein Condensates on Telomeres

Published on: April 12, 2021

3.7K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.6K
Visualization of ATP Synthase Dimers in Mitochondria by Electron Cryo-tomography
10:39

Visualization of ATP Synthase Dimers in Mitochondria by Electron Cryo-tomography

Published on: September 14, 2014

31.0K

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Peripherally strapped [28]hexaphyrins adopt a rectangular conformation and display antiaromatic properties.
  • Cyclophane-type dimers offer unique structural and electronic properties for advanced materials.

Purpose of the Study:

  • To synthesize and characterize a cyclophane-type dimer composed of [28]hexaphyrin units.
  • To investigate the structural, optical, and electronic properties of the synthesized dimer.
  • To determine the presence or absence of three-dimensional aromaticity in the dimer.

Main Methods:

  • Synthesis of the dimer from hexakis(pentafluorophenyl) [26]hexaphyrin via SN Ar reaction with allyl alcohol.
  • One-pot simultaneous intra- and intermolecular olefin metathesis using improved Hoveyda-Grubbs catalysis.
  • Final reduction step using sodium borohydride (NaBH4).
  • Structural elucidation using X-ray crystallography.

Main Results:

  • Successful synthesis of the cyclophane-type dimer of [28]hexaphyrins.
  • X-ray analysis confirmed the cyclophane structures of both [26]- and [28]hexaphyrin dimers.
  • Studies indicated no significant electronic interaction between the two [28]hexaphyrin segments within the dimer.

Conclusions:

  • The synthesized [28]hexaphyrin dimer does not exhibit three-dimensional aromaticity.
  • The lack of electronic communication between the hexaphyrin units is a key finding.
  • This study provides insights into the electronic behavior of complex macrocyclic systems.