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

4.1K
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,...
4.1K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.2K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.2K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
2.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
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.
2.4K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.2K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
3.2K

You might also read

Related Articles

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

Sort by
Same author

Concise synthesis of triasteranones from barbaralones.

Chemical communications (Cambridge, England)·2026
Same author

Protein Nanocarriers: Targeted Theranostics for Cancer Treatment and Imaging.

Cancers·2026
Same author

Visualizing nanostructures in supramolecular hydrogels: a correlative study using confocal and cryogenic scanning electron microscopy.

Beilstein journal of nanotechnology·2025
Same author

Synthesis of <i>S</i>-allylic sulfinamides by the catalytic nucleophilic allylation of <i>N</i>-sulfinylamines.

Organic & biomolecular chemistry·2025
Same author

Visible light photo-switching in a conformationally-strained electron acceptor <i>via</i> a dual singlet-triplet mechanism.

Chemical science·2025
Same author

Co-encapsulation of temozolomide and PbS quantum dots in apoferritin for transferrin receptor 1 targeting, imaging and treatment of glioblastoma.

Nanoscale advances·2025

Related Experiment Video

Updated: Aug 14, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.3K

Highly electron deficient diketopyrrolopyrroles.

Joshua Humphreys1, Ferdinando Malagreca1,2, Paul A Hume3

  • 1GSK Carbon Neutral Laboratories for Sustainable Chemistry, School of Chemistry, University of Nottingham, Triumph Road, Nottingham, NG7 2TU, UK.

Chemical Communications (Cambridge, England)
|January 12, 2023
PubMed
Summary

New diketopyrrolopyrrole (DPP) molecules with pyridinium rings exhibit reversible electrochemistry and low toxicity. Electrochemical reduction significantly enhances their light absorption, indicating potential for advanced electronic applications.

More Related Videos

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K

Related Experiment Videos

Last Updated: Aug 14, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.3K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K

Area of Science:

  • Organic chemistry
  • Materials science
  • Electrochemistry

Background:

  • Diketopyrrolopyrrole (DPP) derivatives are widely studied for their electronic properties.
  • Developing molecules with strong electron-accepting capabilities is crucial for organic electronics.
  • Pyridinium moieties can modulate molecular properties and introduce unique functionalities.

Purpose of the Study:

  • To synthesize and characterize novel diketopyrrolopyrrole (DPP) molecules incorporating pyridinium rings.
  • To investigate the spectroelectrochemical and structural properties of these new DPP compounds.
  • To assess the toxicity profile of the synthesized molecules.

Main Methods:

  • Organic synthesis for creating DPP-pyridinium molecules.
  • Spectroelectrochemistry to study electronic transitions and redox behavior.
  • X-ray crystallography for structural elucidation.
  • Cytotoxicity assays for toxicity assessment.

Main Results:

  • Successful synthesis of highly electron-accepting DPP molecules with adjoining pyridinium rings.
  • Demonstrated reversible electrochemistry for the synthesized compounds.
  • Observed a significant increase in molar extinction coefficient upon electrochemical reduction in one subfamily.
  • Reported apparently low toxicity for the studied molecules.

Conclusions:

  • The novel DPP-pyridinium molecules possess promising electronic and optical properties.
  • Reversible electrochemistry and enhanced light absorption upon reduction suggest potential applications in electrochromic devices or organic electronics.
  • The low toxicity profile is advantageous for further development and potential biological applications.