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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

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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Monitoring the Effects of Illumination on the Structure of Conjugated Polymer Gels Using Neutron Scattering

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Published on: December 21, 2017

Conjugated polymer-porphyrin complexes for organic electronics.

Rolf E Andernach¹, Stephan Rossbauer, Raja S Ashraf

¹Centre for Plastic Electronics, Imperial College London, London SW7 2AZ (UK).

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry

|January 27, 2015

Summary

We developed new polymer-porphyrin materials for organic electronics. These novel conjugated polymers show improved performance and morphology control in organic field-effect transistors.

Keywords:

energy conversion polymers porphyrins semiconductors solar cells

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

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Published on: October 18, 2018

Area of Science:

Materials Science
Organic Electronics
Polymer Chemistry

Background:

Conjugated polymers are crucial for organic electronics.
Controlling polymer morphology is key to enhancing device performance.
Porphyrins offer unique optical and electronic properties.

Purpose of the Study:

To synthesize novel conjugated polymer-porphyrin complexes.
To investigate the effect of porphyrin stacking and dimensionality on polymer morphology.
To enhance the performance of organic electronic devices.

Main Methods:

Synthesis of linear and star-shaped platinated porphyrins.
Attachment of porphyrins to regioregular poly(3-hexylthiophene-2,5-diyl) (P3HT) arms.
Characterization using optical spectroscopy and atomic force microscopy.
Fabrication and testing of organic field-effect transistors (OFETs).

Main Results:

Novel polymer-porphyrin complexes were successfully synthesized.
Materials exhibited optical properties similar to P3HT.
Incorporation of porphyrins led to increased aggregation and altered polymer morphology.
Organic field-effect transistors fabricated with these materials showed higher charge carrier mobilities.

Conclusions:

Conjugatively linked porphyrins effectively tune polymer morphology.
Increased porphyrin dimensionality and stacking enhance aggregation and performance.
These materials represent a promising advancement for organic electronics.