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

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

1.8K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
1.8K
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

32.5K
sp3d and sp3d 2 Hybridization
32.5K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

9.2K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
9.2K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

47.4K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
47.4K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

9.3K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
9.3K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
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.
2.7K

You might also read

Related Articles

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

Sort by
Same author

Identification of π-Stacking Motifs in Naphthalene Diimides via Solid-State NMR.

Journal of the American Chemical Society·2025
Same author

Stack bonding in pentacene and its derivatives.

Physical chemistry chemical physics : PCCP·2025
Same author

The effect of metalation on antimicrobial piscidins imbedded in normal and oxidized lipid bilayers.

RSC chemical biology·2023
Same author

Molecular Dynamics Simulations of Reduced and Oxidized TFIIIA Zinc Fingers Free and Interacting with 5S RNA.

Journal of chemical information and modeling·2022
Same author

A Halogen Bonding Perspective on Iodothyronine Deiodinase Activity.

Molecules (Basel, Switzerland)·2020
Same author

Halogen Bonding Interactions of Polychlorinated Biphenyls and the Potential for Thyroid Disruption.

Chemistry (Weinheim an der Bergstrasse, Germany)·2019

Related Experiment Video

Updated: Jul 23, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K

Stack bonding in polyaromatic hydrocarbons.

Craig A Bayse1

  • 1Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia 23529, USA. cbayse@odu.edu.

Physical Chemistry Chemical Physics : PCCP
|July 19, 2023
PubMed
Summary

Parallel displacement in organic semiconductors boosts efficiency by enhancing π-density overlap. This study reveals favored dimer conformations in polyaromatic hydrocarbons, optimizing π-stacking interactions for improved electronic properties.

More Related Videos

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
09:16

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

Published on: May 20, 2019

7.7K
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

7.9K

Related Experiment Videos

Last Updated: Jul 23, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K
Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
09:16

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

Published on: May 20, 2019

7.7K
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

7.9K

Area of Science:

  • Materials Science
  • Physical Chemistry
  • Organic Electronics

Background:

  • Efficient organic semiconductors rely on maximizing π-density overlap between stacked molecules.
  • Polyaromatic hydrocarbons (PAHs) are key components in organic electronic materials.
  • Understanding π-stacking interactions is crucial for designing high-performance organic semiconductors.

Purpose of the Study:

  • To investigate how parallel displacement affects π-stacking interactions in PAH dimers.
  • To determine energetically favored conformations for efficient π-density interpenetration.
  • To correlate stacking geometries with electronic properties for organic semiconductor design.

Main Methods:

  • Density functional theory (DFT) calculations were employed.
  • Analysis of π-stacking interactions from a stack bonding perspective.
  • Examination of monomer π-orbital overlap and dimer orbital character.

Main Results:

  • Energetically favored parallel displaced and twisted dimer conformations were identified.
  • These conformations maximize π-density interpenetration by optimizing molecular orbital mixing.
  • Multiple minima along parallel displacement coordinates correspond to bonding interactions, unlike the antibonding nature of the sandwich conformation.

Conclusions:

  • Parallel displacement is a key strategy for enhancing organic semiconductor efficiency.
  • Favorable stack bonding minima align with observed polymorphs in large PAHs.
  • The findings provide insights into designing molecular arrangements for superior electronic performance.