A combined theoretical and experimental approach to the study of the structural and electronic properties of curcumin as a function of the solvent

Enrico Benassi, Ferdinando Spagnolo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Curcumin, a chemical compound present in the well-known Indian spice turmeric, has uses in many different fields ranging from medicinal chemistry to the dye industry. Its poor water solubility, though, makes Curcumin difficult to handle, making it less appealing for potential uses. The principal aim of this work is to perform a computational study of the structural and electronic properties of Curcumin {IUPAC name: 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6- heptadiene-3,5-dione} in several solvents, and a comparison with experimental data. Rotameric equilibria, vibrational and thermochemical analysis, and electronic absorption spectra (with ab initio and semi-empirical methodologies) have been studied, both in vacuum and in three selected solvents. Different computational techniques have been applied and the results compared. Combined approaches resulted in very satisfactory results. Interesting results have emerged, which suggest subsequent investigations about the nature of the excited states and potential derivatives of Curcumin that possibly have non-linear optical applications, as a π-core for innovative materials in laser engineering and photonics.

Original languageEnglish
Pages (from-to)11-29
Number of pages19
JournalJournal of Solution Chemistry
Volume39
Issue number1
DOIs
Publication statusPublished - 1 Jan 2010
Externally publishedYes

Fingerprint

Curcumin
Electronic properties
Structural properties
heptadiene
chemical compounds
Dione
electronics
electronic spectra
solubility
dyes
industries
engineering
photonics
methodology
Optics and Photonics
chemistry
absorption spectra
Curcuma
Spices
vacuum

Keywords

  • Absorption electronic spectra
  • CS INDO CI
  • Curcumin
  • Density Functional Theory
  • Hartree-Fock
  • Molecular quantum mechanics
  • Solvent effect
  • TD-SCF

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Physical and Theoretical Chemistry

Cite this

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AB - Curcumin, a chemical compound present in the well-known Indian spice turmeric, has uses in many different fields ranging from medicinal chemistry to the dye industry. Its poor water solubility, though, makes Curcumin difficult to handle, making it less appealing for potential uses. The principal aim of this work is to perform a computational study of the structural and electronic properties of Curcumin {IUPAC name: 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6- heptadiene-3,5-dione} in several solvents, and a comparison with experimental data. Rotameric equilibria, vibrational and thermochemical analysis, and electronic absorption spectra (with ab initio and semi-empirical methodologies) have been studied, both in vacuum and in three selected solvents. Different computational techniques have been applied and the results compared. Combined approaches resulted in very satisfactory results. Interesting results have emerged, which suggest subsequent investigations about the nature of the excited states and potential derivatives of Curcumin that possibly have non-linear optical applications, as a π-core for innovative materials in laser engineering and photonics.

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