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 Experiment Videos

Unusual solid-state behavior in a neutral [2]catenane bearing a hydrolyzable component.

Gary D Fallon1, Marcia A-P Lee, Steven J Langford

  • 1School of Chemistry and Centre for Green Chemistry, Monash University, Clayton, Victoria 3800, Australia.

Organic Letters
|February 28, 2004
PubMed
Summary

Researchers developed a template-directed method to create a bis(diimide) macrocycle using an asymmetric [2]catenane intermediate. This mechanically interlocked structure significantly slows ester linkage saponification, forming infinite channels in the crystal lattice.

Related Concept Videos

You might also read

Related Articles

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

Sort by
Same author

Challenges and Design Strategies for Stable Zinc Anodes in Rechargeable Zinc Batteries.

Small (Weinheim an der Bergstrasse, Germany)·2025
Same author

Stabilizing Dye-Sensitized Upconversion Hybrids by Cyclooctatetraene.

Nano letters·2024
Same author

Aggregation-Induced Emission of Naphthalene Diimides: Effect of Chain Length on Liquid and Solid-Phase Emissive Properties.

Chemistry, an Asian journal·2024
Same author

Retraction of "A Core-Substituted Naphthalene Diimide Fluoride Sensor".

Organic letters·2024
Same author

Defective 2D silicon phosphide monolayers for the nitrogen reduction reaction: a DFT study.

Nanoscale·2022
Same author

p-Block element-doped silicon nanowires for nitrogen reduction reaction: a DFT study.

Nanoscale·2021

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Mechanically interlocked molecules offer unique properties due to their topological constraints.
  • Crown ethers are known for their ability to complex cations and their susceptibility to hydrolysis.
  • Controlling the self-assembly of complex molecular architectures is a key challenge in chemistry.

Purpose of the Study:

  • To report a novel template-directed strategy for synthesizing bis(diimide) macrocycles.
  • To investigate the impact of mechanical interlocking on the reactivity of crown ether components.
  • To explore the self-assembly behavior and crystal packing of the resulting macrocyclic structures.

Main Methods:

  • Template-directed synthesis utilizing an asymmetric [2]catenane intermediate.

Related Experiment Videos

  • Comparative kinetic studies of ester linkage saponification in interlocked vs. free crown ether systems.
  • Single-crystal X-ray diffraction analysis to determine the solid-state structure and packing.

    • Main Results:

    • Successful formation of a bis(diimide) macrocycle via a [2]catenane intermediate.
    • Significantly reduced rate of ester hydrolysis in the mechanically interlocked crown ether compared to the free analog.
    • Observation of a predominant single translational isomer leading to a dimeric structure.
    • Generation of infinite channels within the crystal lattice due to the ordered dimeric assembly.

    Conclusions:

    • Template-directed synthesis provides an effective route to complex mechanically interlocked molecules.
    • Mechanical interlocking can modulate the chemical stability of molecular components.
    • The specific translational isomerism dictates the supramolecular assembly and resulting material properties, such as porosity.