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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.
RSC Advances
|June 9, 2023
Summary
Berberine from tree turmeric was studied using spectroscopy and quantum calculations. Its electronic properties are suitable for creating new donor-acceptor polymers.
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.
