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 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...
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...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

You might also read

Related Articles

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

Sort by
Same author

Taurine Boosts Cellular Uptake of Small D-Peptides for Enzyme-Instructed Intracellular Molecular Self-Assembly.

Journal of the American Chemical Society·2015
Same author

Diameter-Axial-Polar Nephrometry is Predictive of Surgical Outcomes Following Partial Nephrectomy.

Medicine·2015
Same author

Assessing visual green effects of individual urban trees using airborne Lidar data.

The Science of the total environment·2015
Same author

A New Ligustrazine Derivative-Selective Cytotoxicity by Suppression of NF-κB/p65 and COX-2 Expression on Human Hepatoma Cells. Part 3.

International journal of molecular sciences·2015
Same author

Organ and effective dose evaluation in coronary angiography by using a 320 MDCT based on in-phantom dose measurements with TLDs.

Journal of radiological protection : official journal of the Society for Radiological Protection·2015
Same author

High Strength Multifunctional Multiwalled Hydrogel Tubes: Ion-Triggered Shape Memory, Antibacterial, and Anti-inflammatory Efficacies.

ACS applied materials & interfaces·2015
Same journal

The role of spacer length and flexibility in peptide self-assembly.

Beilstein journal of organic chemistry·2026
Same journal

Novel macrocycles: from synthesis to supramolecular function.

Beilstein journal of organic chemistry·2026
Same journal

Electrochemical reduction of unsaturated carbon-carbon bonds via 3d transition-metal catalysis.

Beilstein journal of organic chemistry·2026
Same journal

Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones.

Beilstein journal of organic chemistry·2026
Same journal

Chiral cyclopropenimine-catalyzed enantioselective Michael reactions of phenol and benzofuran-derived α,β-unsaturated pyrazolamides with benzophenone-imine of glycine esters.

Beilstein journal of organic chemistry·2026
Same journal

A practical CO<sub>2</sub>-mediated synthesis of 5,6-carboxylated silicon-rhodamines for targeted probe development.

Beilstein journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Jun 3, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Exceptionally small supramolecular hydrogelators based on aromatic-aromatic interactions.

Junfeng Shi1, Yuan Gao, Zhimou Yang

  • 1Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453.

Beilstein Journal of Organic Chemistry
|March 31, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed novel small molecule hydrogelators using aromatic-aromatic interactions. The lowest molecular weight peptide-based hydrogelator to date, compound 6, forms self-assembled molecular nanofibers in water.

Keywords:
aromatic–aromatic interactioncinnamoylhydrogelhydrogelatorsupramolecular

More Related Videos

Synthesis of Poly(N-isopropylacrylamide) Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability
09:09

Synthesis of Poly(N-isopropylacrylamide) Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability

Published on: February 27, 2016

Thermal Scanning Conductometry (TSC) as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels
10:01

Thermal Scanning Conductometry (TSC) as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels

Published on: January 23, 2018

Related Experiment Videos

Last Updated: Jun 3, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
16:24

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water

Published on: August 2, 2012

Synthesis of Poly(N-isopropylacrylamide) Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability
09:09

Synthesis of Poly(N-isopropylacrylamide) Janus Microhydrogels for Anisotropic Thermo-responsiveness and Organophilic/Hydrophilic Loading Capability

Published on: February 27, 2016

Thermal Scanning Conductometry (TSC) as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels
10:01

Thermal Scanning Conductometry (TSC) as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels

Published on: January 23, 2018

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Aromatic-aromatic interactions are crucial for molecular self-assembly.
  • Developing low molecular weight hydrogelators is essential for advanced materials.

Purpose of the Study:

  • To synthesize and characterize novel small molecule hydrogelators.
  • To investigate the self-assembly behavior of these compounds in water.
  • To explore the potential of aromatic-aromatic interactions in hydrogel formation.

Main Methods:

  • Synthesis of small molecule hydrogelators.
  • Self-assembly studies in aqueous solutions.
  • Characterization using Transmission Electron Microscopy (TEM) and fluorescence spectroscopy.
  • Rheological property analysis.

Main Results:

  • Successfully produced small molecule hydrogelators that self-assemble into molecular nanofibers.
  • Identified compound 6, derived from phenylalanine and a cinnamoyl group, as the lowest molecular weight peptide-based hydrogelator (MW = 295.33 g/mol).
  • TEM and fluorescence spectroscopy results correlated well with rheological properties.
  • Compound 6 exhibited UV-induced cis/trans-isomerization.

Conclusions:

  • Aromatic-aromatic interactions effectively drive the formation of hydrogels from small molecules.
  • Compound 6 represents a significant advancement in peptide-based hydrogelator design.
  • The characterized hydrogels possess tunable properties suitable for various applications.
  • Photoisomerization capability offers potential for stimuli-responsive materials.