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

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
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.1K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.8K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.8K
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

1.8K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1.8K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.4K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.4K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.6K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
16.6K

You might also read

Related Articles

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

Sort by
Same author

5,12-TIPS-Substitution of Tetracene: Effects on Redox Potentials and Cyclic Voltammetric Behavior in CH<sub>2</sub>Cl<sub>2</sub> and THF.

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

RE-ADC: The algebraic diagrammatic construction scheme for the polarization propagator using the retaining-the-excitation-degree partitioning.

The Journal of chemical physics·2026
Same author

Ethynylene-Linked 1,2-Dihydro-1,2-Azaborinines With High Energy Densities for Efficient Molecular Solar Thermal Energy Storage.

ChemSusChem·2026
Same author

Green circularly polarized luminescence with a high dissymmetry factor emitted by a [2.2]fluorenonophane.

Physical chemistry chemical physics : PCCP·2026
Same author

The Nodal Structure of π-Orbitals Is Mapped in the Interaction Energy of π-Stacked Acene Dimers.

Journal of the American Chemical Society·2026
Same author

Revisiting acene dimers: A comprehensive theoretical study of a less explored conformer.

The Journal of chemical physics·2026

Related Experiment Video

Updated: Mar 6, 2026

Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes
09:47

Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes

Published on: February 19, 2016

10.2K

Heptacene: Characterization in Solution, in the Solid State, and in Films.

Ralf Einholz1, Treliant Fang2, Robert Berger3,4

  • 1Institut für Organische Chemie, Universität Tübingen , Auf der Morgenstelle 18, 72076 Tübingen, Germany.

Journal of the American Chemical Society
|March 21, 2017
PubMed
Summary

Researchers synthesized bulk heptacene, a key organic semiconductor, using diheptacene precursors. This breakthrough allows for the study of heptacene's properties in solid form at room temperature.

More Related Videos

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
08:18

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

2.2K
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

12.1K

Related Experiment Videos

Last Updated: Mar 6, 2026

Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes
09:47

Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes

Published on: February 19, 2016

10.2K
Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
08:18

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

2.2K
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

12.1K

Area of Science:

  • Organic electronics
  • Nanoscale carbon materials
  • Acene chemistry

Background:

  • Acenes are crucial organic semiconductors and atom-precise models for graphene nanoribbons.
  • Heptacene, the smallest acene, has historically been limited to matrix isolation studies.
  • Confirming bulk heptacene has been a long-standing challenge in materials science.

Purpose of the Study:

  • To synthesize and characterize bulk heptacene.
  • To investigate the stability and properties of solid-state heptacene.
  • To establish a method for generating heptacene films for further study.

Main Methods:

  • Reduction of 7,16-heptacenequinone to form diheptacene molecules.
  • Thermal cleavage of diheptacenes to generate heptacene in the solid state.
  • Solid-state 13C cross-polarized magic angle spinning NMR for monitoring cycloreversion and stability.

Main Results:

  • Successful synthesis of diheptacene precursors.
  • Demonstration of thermal cleavage of diheptacenes to produce heptacene.
  • Determination of solid heptacene's room temperature half-life of several weeks.
  • Development of diheptacenes as precursors for vapor-deposited heptacene films.

Conclusions:

  • Diheptacenes are effective precursors for generating solid-state heptacene.
  • Solid heptacene is stable enough at room temperature for characterization.
  • This work overcomes a 70-year challenge, enabling new studies of nanoscale carbon materials.