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Updated: Jul 27, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Berberine isolation from

R M Gamini Rajapakse¹, Benjamin R Horrocks², A U Malikaramage¹

¹Department of Chemistry, Faculty of Science, University of Peradeniya Peradeniya 20400 Sri Lanka rmgr1521961@gmail.com.

|June 9, 2023

Summary

This summary is machine-generated.

Berberine from tree turmeric was studied using spectroscopy and quantum calculations. Its electronic properties are suitable for creating new donor-acceptor polymers.

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Area of Science:

Photochemistry
Computational Chemistry
Materials Science

Background:

Berberine, a natural alkaloid from Coscinium fenestratum (tree turmeric), possesses interesting photophysical properties.
Understanding berberine's electronic structure is crucial for its application in advanced materials.
Previous studies have explored berberine's biological activities, but its detailed electronic and electrochemical behavior requires further investigation.

Purpose of the Study:

To characterize the UV-Vis absorption and emission spectra of berberine in different media.
To computationally investigate the electronic transitions and charge transfer characteristics of berberine.
To determine the electrochemical gap and assess its potential for polymerization into donor-acceptor materials.

Main Methods:

Extraction and purification of berberine from Coscinium fenestratum using column chromatography.
UV-Vis absorption spectroscopy in acetonitrile and aqueous solutions.
Time-Dependent Density Functional Theory (TD-DFT) calculations with B3LYP functional.
Microelectrode voltammetry for electrochemical gap determination.
Quantum chemical calculations using cc-pVTZ basis set with B3LYP, CAM-B3LYP, and wB97XD functionals.

Main Results:

TD-DFT calculations accurately reproduced the main features of berberine's absorption and emission spectra.
Electronic transitions involve electron density transfer from the methylenedioxy phenyl ring to the isoquinolium moiety.
Electrochemical gap estimated at 2.64 V from voltammetry, showing good agreement with quantum chemical calculations.
Calculations indicate delocalized spin density in the radical dication of berberine.

Conclusions:

Berberine exhibits electronic properties consistent with a donor-acceptor system.
The calculated electronic transitions and electrochemical gap provide valuable data for material design.
Berberine is a promising candidate for synthesizing novel donor-acceptor polymeric materials via oxidative or co-polymerization.