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

2.0K
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...
2.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.0K
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...
4.0K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.0K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
4.0K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
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...
4.1K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.9K
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,...
5.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.8K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.8K

You might also read

Related Articles

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

Sort by
Same author

Diagnostic delay and onset-anchored clinical milestones in progressive supranuclear palsy: a japanese single-center retrospective cohort study.

Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology·2026
Same author

Inner-Bond Cleavage of Sterically Congested Dibenzo[<i>g</i>,<i>p</i>]chrysene to a Rigid Figure-Eight Macrocycle.

Organic letters·2026
Same author

Molecular Crystals With Reversible Chromic Three-State Crystal-to-Crystal Transformation via the Dynamic Motion of Negatively Curved π-Frameworks.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Early respiratory decline around diagnosis and short-term post-landmark outcomes in amyotrophic lateral sclerosis: a 6-month landmark cohort study.

Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology·2026
Same author

Electrochemical Wiring of a Metal Nanofilament to Form a Molecular Junction.

The journal of physical chemistry letters·2026
Same author

Anchoring-group-controlled self-assembly and charge transport in antiaromatic molecular systems.

Nanoscale·2026

Related Experiment Video

Updated: Feb 26, 2026

Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates
08:07

Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates

Published on: June 18, 2013

15.5K

Highly-conducting molecular circuits based on antiaromaticity.

Shintaro Fujii1, Santiago Marqués-González1, Ji-Young Shin2

  • 1Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.

Nature Communications
|July 20, 2017
PubMed
Summary

Researchers measured the charge transport properties of antiaromatic compounds, finding they have significantly higher electrical conductance than aromatic molecules. This discovery opens possibilities for novel electronic devices using antiaromaticity.

More Related Videos

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.7K
1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

8.3K

Related Experiment Videos

Last Updated: Feb 26, 2026

Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates
08:07

Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates

Published on: June 18, 2013

15.5K
Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.7K
1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
06:56

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

8.3K

Area of Science:

  • Organic Chemistry
  • Molecular Electronics
  • Quantum Chemistry

Background:

  • Aromaticity, defined by Hückel's rule, classifies cyclic π-systems as aromatic (4n+2 π-electrons) or antiaromatic (4n π-electrons).
  • Antiaromatic compounds are theoretically predicted to possess high charge transport capabilities and redox activity.
  • The experimental investigation of antiaromatic compounds has been limited due to their inherent energetic instability.

Purpose of the Study:

  • To investigate the single-molecule charge transport properties of a genuinely antiaromatic compound.
  • To compare the conductance of antiaromatic species with their aromatic counterparts.
  • To explore the potential of antiaromatic compounds in molecular electronics.

Main Methods:

  • Single-molecule current-voltage measurements.
  • Ab initio transport calculations.
  • Electrochemical modulation of conductance.

Main Results:

  • Antiaromatic compounds exhibit an order of magnitude increase in electrical conductance compared to aromatic compounds.
  • This enhanced conductance is attributed to a reduced energy gap and a frontier molecular resonance near the Fermi level.
  • The conductance of the antiaromatic complex can be tuned electrochemically.

Conclusions:

  • Antiaromaticity significantly enhances molecular conductance.
  • The findings demonstrate the potential of antiaromatic compounds as components in high-conductance molecular transistors.
  • This work overcomes previous limitations in studying unstable antiaromatic species, paving the way for their application in electronic devices.