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Related Concept Videos

Redox Reactions01:24

Redox Reactions

Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
Redox Reactions01:27

Redox Reactions

Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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...
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.
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
Redox Equilibria: Overview01:23

Redox Equilibria: Overview

A reduction-oxidation reaction is commonly called a redox reaction. In a redox reaction, electrons are transferred from one species to another rather than being shared between or among atoms. The reducing agent or reductant is the species that loses electrons and gets oxidized in the process. The species that gains electrons and gets reduced in the process is the oxidizing agent or oxidant. Redox reactions are represented as two separate equations called half-reactions, where one equation...

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

A neutral redox-switchable [2]rotaxane.

J-C Olsen1, A C Fahrenbach, A Trabolsi

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.

Organic & Biomolecular Chemistry
|September 1, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed a new neutral, redox-active rotaxane molecular switch. This robust bistable switch, featuring pyromellitic diimide, dioxynaphthalene, and tetrathiafulvalene units, shows promise for nanoscale devices.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Limited availability of redox-active, rotaxane-based molecular switches hinders nanoscale device development.
  • Rotaxanes offer unique mechanically interlocked structures for molecular machinery.

Purpose of the Study:

  • To design and synthesize a novel neutral, redox-active [2]rotaxane molecular switch.
  • To investigate its potential for bistable switching applications in nanoscale devices.

Main Methods:

  • Molecular modeling (MacroModel) for rational design.
  • Synthesis via neutral donor-acceptor templation and copper-catalyzed azide-alkyne cycloaddition (CuAAC).
  • Characterization using cyclic voltammetry (CV), spectroelectrochemistry (SEC), and 1H NMR spectroscopy.

Main Results:

  • A neutral [2]rotaxane incorporating pyromellitic diimide (PmI), dioxynaphthalene (DNP), and tetrathiafulvalene (TTF) units was successfully synthesized (34% yield).
  • Strong binding affinities were observed between the PmI ring and DNP/TTF recognition sites.
  • The rotaxane demonstrated bistable switching behavior in solution via electrochemical and chemical oxidation stimuli.

Conclusions:

  • The synthesized neutral [2]rotaxane functions as a chemically robust and bistable molecular switch.
  • This molecular switch holds significant potential for integration into advanced nanoscale devices.
  • The study highlights the feasibility of integrating DNP, TTF, and PmI units into functional rotaxane switches.