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

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

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

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...

You might also read

Related Articles

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

Sort by
Same author

Alternating Current-Driven Hydrogen Isotope Labeling of Aliphatic Amines Using 1,3-Propanedithiol as an Efficient Hydrogen Atom Transfer Reagent.

Journal of the American Chemical Society·2026
Same author

Cobalt-Catalyzed Asymmetric Cyclopropanation of Heteroaryl Alkenes with Homogeneous Zinc Carbenoids.

Journal of the American Chemical Society·2026
Same author

Leukemia Cutis at Initial Diagnosis of Acute Myeloid Leukemia Consistent With Therapy-Related Disease After Lung Cancer Chemotherapy: A Case Report.

Case reports in hematology·2026
Same author

Progress towards the elimination of vertical transmission of HIV, syphilis and hepatitis B in 21 high-burden countries.

Journal of the International AIDS Society·2026
Same author

Synthesis of Conjugated Linear and Cyclic Polyynes by Selective Alkyne Metathesis.

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

The versatile world of cumulene chemistry.

Chemical science·2025

Related Experiment Video

Updated: Jul 2, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

Exploring electronically polarized pentacenes.

Dan Lehnherr1, Robert McDonald, Rik R Tykwinski

  • 1Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.

Organic Letters
|September 4, 2008
PubMed
Summary
This summary is machine-generated.

New unsymmetrical pentacene molecules were created with tunable electronic properties. These stable, soluble organic materials show promise for various electronic applications.

More Related Videos

Using Neutron Spin Echo Resolved Grazing Incidence Scattering to Investigate Organic Solar Cell Materials
06:05

Using Neutron Spin Echo Resolved Grazing Incidence Scattering to Investigate Organic Solar Cell Materials

Published on: January 15, 2014

Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds
09:11

Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds

Published on: October 12, 2018

Related Experiment Videos

Last Updated: Jul 2, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

Using Neutron Spin Echo Resolved Grazing Incidence Scattering to Investigate Organic Solar Cell Materials
06:05

Using Neutron Spin Echo Resolved Grazing Incidence Scattering to Investigate Organic Solar Cell Materials

Published on: January 15, 2014

Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds
09:11

Raman and IR Spectroelectrochemical Methods as Tools to Analyze Conjugated Organic Compounds

Published on: October 12, 2018

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Pentacenes are a class of organic semiconductors with potential applications in organic electronics.
  • Controlling the electronic properties of pentacenes is crucial for optimizing their performance.
  • Functionalization of pentacene cores allows for tuning of their optoelectronic characteristics.

Purpose of the Study:

  • To synthesize unsymmetrically functionalized pentacenes with diverse electronic properties.
  • To investigate the impact of electron-rich and/or -poor substituents on pentacene behavior.
  • To evaluate the stability and solubility of these novel pentacene derivatives.

Main Methods:

  • Synthesis of unsymmetrically substituted pentacene derivatives.
  • Solution-state ultraviolet-visible (UV-vis) absorption spectroscopy.
  • Solution-state emission spectroscopy.

Main Results:

  • Successful synthesis of pentacene derivatives with substituents at the 6- and 13-positions.
  • Demonstrated tunability of electronic properties through substituent choice, as evidenced by spectroscopic data.
  • Observed good solubility in common organic solvents.
  • Confirmed stability in the presence of air and water.

Conclusions:

  • Unsymmetrical functionalization provides a viable route to tailor pentacene electronic properties.
  • The synthesized pentacenes possess favorable solubility and stability for practical applications.
  • These materials represent promising candidates for advanced organic electronic devices.