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Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Redox Reactions

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...

Thermal and Photochemical Electrocyclic Reactions: Overview

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.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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Published on: January 30, 2015

π-Conjugated redox-active two-dimensional polymers as organic cathode materials.

Zexin Jin¹, Qian Cheng¹, Austin M Evans¹

¹Department of Chemistry, Columbia University New York New York 10027 USA zj2286@columbia.edu cn37@columbia.edu.

Chemical Science

|April 18, 2022

Summary

New π-conjugated redox-active two-dimensional polymers (RA-2DPs) overcome conductivity limits in organic cathode materials. These advanced polymers demonstrate high performance and stability for lithium batteries, enabling practical applications like powering LED lights.

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

Area of Science:

Materials Science
Electrochemistry
Polymer Chemistry

Background:

Redox-active two-dimensional polymers (RA-2DPs) show promise for lithium battery organic cathodes due to porosity and stability.
Limited electrical conductivity in existing RA-2DPs hinders their practical application and device performance.

Purpose of the Study:

To develop π-conjugated RA-2DPs with enhanced electrical conductivity.
To improve the performance and practical relevance of organic cathode materials for lithium batteries.

Main Methods:

A modular synthesis approach using a novel polycyclic aromatic building block (PDI-DA).
Imine-condensation reactions followed by alkyl chain removal to form conjugated, porous networks (TAPPy-PDI and TAPB-PDI).

Main Results:

Synthesized π-conjugated RA-2DPs (TAPPy-PDI and TAPB-PDI) with inherent porosity and high electrical conductivity.
Demonstrated excellent rate performance and cycling stability for these materials as organic cathode materials.
Achieved higher areal mass-loadings, enabling a practical demonstration powering LED lights.

Conclusions:

The developed synthetic methodologies and design principles enable high-performance organic cathode materials.
π-conjugation and permanent porosity are key factors for enhancing conductivity and ion diffusion in RA-2DPs.
These findings pave the way for advanced organic electrode materials in energy storage devices.