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

Versatile self-complexing compounds based on covalently linked donor-acceptor cyclophanes.

Yi Liu1, Amar H Flood, Ross M Moskowitz

  • 1California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095-1569, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 25, 2004
PubMed
Summary
This summary is machine-generated.

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

Transient and Regulated Cycles of Chemically Driven Disassembly and Reassembly in Anion-Driven Supramolecular Polymers.

Journal of the American Chemical Society·2026
Same author

Highly coherent organic lasing based on etch-free metasurface.

Nature communications·2025
Same author

Self-assembly and Lateral Cobalt Coordination of a Fivefold Symmetric Cyanostar Macrocycle on an Au(111) Surface.

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

Anion Binding by Macrocyclic Receptors: Computational Landscape of 1:1 and 2:1 Stoichiometries.

Journal of computational chemistry·2025
Same author

Multi-Ion Complexes and Competition from Bulky BArF<sup>-</sup> Anions for Chloride Binding in Ion Pairing Conditions.

The Journal of organic chemistry·2025
Same author

Bambusuril Small-Molecule Ionic Isolation Lattices for Exciton Coupled Dimers and Dicationic Fluorophores.

Journal of the American Chemical Society·2025

New molecular machines use temperature-dependent self-complexing/decomplexing equilibria for control. These donor-acceptor compounds, featuring hydroquinone or dioxynaphthalene units, can act as thermo- and electroswitches.

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Covalently linked donor-acceptor compounds are key components in molecular machines.
  • The design of molecules that can undergo controlled conformational changes is crucial for developing advanced functional materials.
  • Cyclic host molecules, such as cyclobis(paraquat-p-phenylene) (CBPQT(4+)), can encapsulate donor moieties through noncovalent interactions.

Purpose of the Study:

  • To synthesize and characterize novel donor-acceptor compounds capable of operating as molecular machines.
  • To investigate the temperature-dependent self-complexing/decomplexing behavior of these compounds.
  • To explore the potential applications of these molecular machines as switches and sensors.

Main Methods:

  • Synthesis of covalently linked donor-acceptor compounds incorporating hydroquinone (HQ), 1,5-dioxynaphthalene (DNP), or tetrathiafulvalene (TTF) as pi-donors and CBPQT(4+) as the pi-accepting tetracationic cyclophane.

Related Experiment Videos

  • Variable-temperature (1)H NMR spectroscopy to study self-complexing/decomplexing equilibria and determine thermodynamic parameters.
  • Structural analysis to understand the influence of bulky substituents on molecular motion.

    • Main Results:

    • The self-complexing/decomplexing equilibria of HQ- and DNP-containing compounds are highly temperature-dependent, with negative enthalpy and entropy changes favoring the uncomplexed state.
    • Molecular motion can be arrested by introducing bulky substituents, leading to distinct conformational behaviors, including diastereoisomeric forms for DNP compounds at low temperatures.
    • TTF-containing compounds exhibit less thermal control but can be manipulated electrochemically and chemically due to TTF's redox activity.

    Conclusions:

    • The synthesized compounds function as simple molecular machines controlled by temperature-induced self-complexing/decomplexing.
    • The thermodynamic parameters provide insights into the driving forces behind the conformational changes.
    • These molecular machines show promise for applications as thermo- and electroswitches, as well as thermochromic imaging and sensing materials.