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

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
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,...
4.5K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
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...
3.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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...
3.1K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

11.9K
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...
11.9K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.1K
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.
3.1K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.6K
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...
11.6K

You might also read

Related Articles

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

Sort by
Same author

Planar Chiral Carbazole-Naphthalene Bisimide Hetero-Cyclophane for Circularly Polarized Delayed Fluorescence.

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

Fluorescent merocyanines: from fundamental properties to applications as molecular probes, in bioimaging and as emissive dye aggregates.

Chemical Society reviews·2026
Same author

Colour by design: tuning the solid-state emission of coronene bisimide by tailored matrices.

Chemical science·2026
Same author

Enzyme-Like Synthetic Cleft for Light-Driven Water-Oxidation Catalysis Via an Oxide Relay Pathway.

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

Distorted Nanographenes by Embedding a Cyclopenta[<i>a</i>]heptalene Core and Multiple Additional Heptagons: Chiral Supramolecular π-Dodecamer and Co-crystal with Fullerenes.

Journal of the American Chemical Society·2026
Same author

Synthesis of an Axially Chiral Quateropyrene by C-H Activation and Benzannulation.

Organic letters·2026

Related Experiment Video

Updated: Oct 4, 2025

Colloidal Synthesis of Nanopatch Antennas for Applications in Plasmonics and Nanophotonics
09:12

Colloidal Synthesis of Nanopatch Antennas for Applications in Plasmonics and Nanophotonics

Published on: May 28, 2016

11.3K

Multilayer stacks of polycyclic aromatic hydrocarbons.

Magnus Mahl1, M A Niyas1, Kazutaka Shoyama1,2

  • 1Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.

Nature Chemistry
|February 8, 2022
PubMed
Summary

Researchers explored multilayered polycyclic aromatic hydrocarbons (PAHs), or nanographenes, for advanced electronics. They successfully assembled novel C64 nanographene derivatives into stacks with smaller PAHs, revealing new material possibilities.

More Related Videos

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

8.0K
Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides
10:27

Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides

Published on: July 14, 2015

10.2K

Related Experiment Videos

Last Updated: Oct 4, 2025

Colloidal Synthesis of Nanopatch Antennas for Applications in Plasmonics and Nanophotonics
09:12

Colloidal Synthesis of Nanopatch Antennas for Applications in Plasmonics and Nanophotonics

Published on: May 28, 2016

11.3K
Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

8.0K
Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides
10:27

Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides

Published on: July 14, 2015

10.2K

Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Organic Electronics

Background:

  • Polycyclic aromatic hydrocarbons (PAHs), particularly nanographenes, are key for organic electronics like photovoltaics and transistors.
  • While single-layer nanographenes are studied, multilayered structures remain underexplored.
  • Developing methods for controlled assembly of multilayered PAHs is crucial for advancing functional materials.

Purpose of the Study:

  • To investigate the assembly of multilayered nanographene structures.
  • To explore the potential of a functionalized C64 nanographene derivative as a host for smaller PAHs.
  • To understand the self-assembly behavior and stabilizing forces in PAH multilayer complexes.

Main Methods:

  • Synthesis of a C64 nanographene derivative with peripheral meta-terphenyl-imide groups.
  • Solution-phase self-assembly of the C64 derivative with smaller PAHs (naphthalene, ovalene, hexabenzocoronene).
  • Characterization of resulting bilayers and trilayers in solution and solid states.
  • Quantum-chemical calculations to determine stabilizing interactions.

Main Results:

  • The C64 nanographene derivative successfully formed ditopic host-guest complexes with smaller PAHs.
  • Bilayers (1:1 host:guest) and trilayers (1:2 host:guest) were observed in solution.
  • Multilayer compounds and dimers of complexes were isolated in the solid state.
  • Quantum-chemical calculations identified dispersion forces as the primary stabilizing factor.

Conclusions:

  • Functionalized C64 nanographene derivatives can act as hosts for assembling multilayered PAH structures.
  • These findings open new avenues for designing complex nanographene architectures for electronic applications.
  • Dispersion forces play a critical role in the stability of these supramolecular PAH assemblies.