Related Experiment Video
Updated: Jun 6, 2026
06:53
Magnetometric Characterization of Intermediates in the Solid-State Electrochemistry of Redox-Active Metal-Organic Frameworks
Published on: June 9, 2023
On/off electrochemical switches based on quinone-bisketals
Noelia Fuentes1, Luis Álvarez de Cienfuegos, Andrés Parra
1Departamento de Química Orgánica, Universidad de Granada, Campus Fuentenueva s/n, E-18071 Granada, Spain.
Chemical Communications (Cambridge, England)
|December 1, 2010
Summary
Researchers synthesized novel quinone bisketals from substituted 1,4-dialkoxybenzenes. Their structural and electrochemical studies suggest these compounds are a potential molecular nanofuse, paving the way for new nanoscale materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Electrochemistry
Background:
- 1,4-dialkoxybenzenes are versatile precursors in organic synthesis.
- Quinone derivatives exhibit unique electronic and redox properties.
- Molecular electronics requires well-defined molecular components.
Purpose of the Study:
- To synthesize and characterize novel quinone bisketals.
- To explore the potential of these compounds as molecular nanofuses.
- To investigate the relationship between structure and electrochemical properties.
Main Methods:
- Anodic oxidation of 2,5-diaryl or dialkynylaryl substituted 1,4-dialkoxybenzenes.
- X-ray crystallography for structural determination.
- Electrochemical and spectroscopic analyses (e.g., cyclic voltammetry, NMR, UV-Vis).
Main Results:
- Successful synthesis of a series of quinone bisketals.
- X-ray structures confirmed the molecular architecture.
- Electrochemical and spectroscopic data indicated tunable redox behavior.
- The synthesized compounds demonstrated properties consistent with a molecular nanofuse concept.
Conclusions:
- The studied quinone bisketals represent a promising molecular architecture.
- These compounds offer a foundational approach to developing molecular nanofuses.
- Further research can explore their application in molecular electronic devices.
Related Concept Videos
01:24Types of Reversible Electrodes
For electrode reversibility to be maintained, all the reactants and products involved in the half-reaction must be present at the electrode. There are several types of reversible electrodes (half-cells).In metal-metal-ion electrodes, a metal balances electrochemically with a solution of its own ions. Examples are Cu2+|Cu and Zn2+|Zn. Metals that react with the solvent, like group 1 and most group 2 metals, which react with water, and zinc, which reacts with aqueous acidic solutions, cannot be...
01:17Oxidation of Phenols to Quinones
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
01:28Electrochemical Cells
Electrochemical cells are systems that convert chemical energy into electrical energy or use electrical energy to drive chemical reactions. They consist of two electrodes in contact with an electrolyte, where redox reactions enable electron transfer. Most electrochemical cells include two half-cells connected by an external wire for electron flow and a salt bridge for ion flow. The salt bridge contains an electrolyte solution and maintains charge neutrality by allowing ions—not electrons—to...
01:24Electrochemical Systems
Electrochemical systems provide a fascinating insight into the dynamic interplay of charged species within various phases. One notable example is the interaction between a membrane permeable to K⁺ ions but not to Cl⁻ ions, separating an aqueous KCl solution from pure water. As K⁺ ions diffuse through the membrane, they generate net charges on each phase, leading to a potential difference between them.Similarly, when a piece of Zn is immersed in an aqueous ZnSO₄ solution, the Zn metal, composed...
02:47Voltaic/Galvanic Cells
Spontaneous Chemical Reactions
Spontaneous redox reactions occur abundantly in nature. The chemical reaction occurring in a disposable AA battery powering our remote controls is one such example of a spontaneous redox reaction. Another example is the immersion of coiled copper wire into an aqueous silver nitrate solution. The reaction shows a gradual, visually impressive color change from colorless to bright blue and the formation of a grey precipitate on the copper wire. In this experiment,...
Spontaneous redox reactions occur abundantly in nature. The chemical reaction occurring in a disposable AA battery powering our remote controls is one such example of a spontaneous redox reaction. Another example is the immersion of coiled copper wire into an aqueous silver nitrate solution. The reaction shows a gradual, visually impressive color change from colorless to bright blue and the formation of a grey precipitate on the copper wire. In this experiment,...
01:30Ladder Diagrams: Redox Equilibria
Ladder diagrams are useful tools for understanding redox equilibrium reactions, especially the effects of concentration changes on the electrochemical potential of the reaction. The vertical axis in the redox ladder diagrams represents the electrochemical potential, E. The area of predominance is demarcated using the Nernst equation.
Consider the Fe3+/Fe2+ half-reaction, which has a standard-state potential of +0.771 V. At potentials more positive than +0.771 V, Fe3+ predominates, whereas Fe2+...
Consider the Fe3+/Fe2+ half-reaction, which has a standard-state potential of +0.771 V. At potentials more positive than +0.771 V, Fe3+ predominates, whereas Fe2+...