Abstract
Curcumin, a well-known Indian spice, holds a variety of properties in many different fields from medicinal chemistry to dye industry. The peculiar electronic structure makes curcumin a valuable metal chelator. The principal aim of this work is a computational study of the structural and electronic properties of the ground and the first singlet excited states of the curcuminoidic core. Concerning the ground state, tautomeric equilibrium, vibrational and thermochemical analysis and electronic absorption spectra (with ab initio and semi-empirical methodologies) have been studied. A full geometry optimization of the first singlet excited states was obtained, with different computational methodologies. Solvent effects are also implicitly considered. An accurate comparison of the results is presented. Interesting aspects emerge, which suggest successive investigation about the nature of the excited states. The obtained results may be of large applicative interest. If curcuminoids are considered as potential ligands for complexes formation with metallic ions of pharmaceutical, medical-physical and technological interest, exciting the system with photons of appropriate frequencies, a photomodulated release of the metallic ion in the environment might be guessed, because of an important photoinduced geometrical modification.
| Original language | English |
|---|---|
| Pages (from-to) | 235-250 |
| Number of pages | 16 |
| Journal | Theoretical Chemistry Accounts |
| Volume | 124 |
| Issue number | 3-4 |
| DOIs | |
| Publication status | Published - 1 Jan 2009 |
| Externally published | Yes |
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Keywords
- 1,7-Diphenyl-1,6-heptadiene-3,5-dione
- 1,7-Diphenyl-5-hydroxy-1,4,6-heptatrien-3-one
- Complete active space multiconfiguration SCF (CAS-SCF)
- Configuration interaction (CI-S)
- CS INDO CI
- Curcuminoid
- Density functional theory (DFT)
- Electronic excited states optimization
- Time-dependent SCF (TD-SCF)
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
Cite this
A theoretical study about the structural, electronic and spectroscopic properties of the ground and singlet excited states of curcuminoidic core. / Benassi, Enrico; Spagnolo, Ferdinando.
In: Theoretical Chemistry Accounts, Vol. 124, No. 3-4, 01.01.2009, p. 235-250.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A theoretical study about the structural, electronic and spectroscopic properties of the ground and singlet excited states of curcuminoidic core
AU - Benassi, Enrico
AU - Spagnolo, Ferdinando
PY - 2009/1/1
Y1 - 2009/1/1
N2 - Curcumin, a well-known Indian spice, holds a variety of properties in many different fields from medicinal chemistry to dye industry. The peculiar electronic structure makes curcumin a valuable metal chelator. The principal aim of this work is a computational study of the structural and electronic properties of the ground and the first singlet excited states of the curcuminoidic core. Concerning the ground state, tautomeric equilibrium, vibrational and thermochemical analysis and electronic absorption spectra (with ab initio and semi-empirical methodologies) have been studied. A full geometry optimization of the first singlet excited states was obtained, with different computational methodologies. Solvent effects are also implicitly considered. An accurate comparison of the results is presented. Interesting aspects emerge, which suggest successive investigation about the nature of the excited states. The obtained results may be of large applicative interest. If curcuminoids are considered as potential ligands for complexes formation with metallic ions of pharmaceutical, medical-physical and technological interest, exciting the system with photons of appropriate frequencies, a photomodulated release of the metallic ion in the environment might be guessed, because of an important photoinduced geometrical modification.
AB - Curcumin, a well-known Indian spice, holds a variety of properties in many different fields from medicinal chemistry to dye industry. The peculiar electronic structure makes curcumin a valuable metal chelator. The principal aim of this work is a computational study of the structural and electronic properties of the ground and the first singlet excited states of the curcuminoidic core. Concerning the ground state, tautomeric equilibrium, vibrational and thermochemical analysis and electronic absorption spectra (with ab initio and semi-empirical methodologies) have been studied. A full geometry optimization of the first singlet excited states was obtained, with different computational methodologies. Solvent effects are also implicitly considered. An accurate comparison of the results is presented. Interesting aspects emerge, which suggest successive investigation about the nature of the excited states. The obtained results may be of large applicative interest. If curcuminoids are considered as potential ligands for complexes formation with metallic ions of pharmaceutical, medical-physical and technological interest, exciting the system with photons of appropriate frequencies, a photomodulated release of the metallic ion in the environment might be guessed, because of an important photoinduced geometrical modification.
KW - 1,7-Diphenyl-1,6-heptadiene-3,5-dione
KW - 1,7-Diphenyl-5-hydroxy-1,4,6-heptatrien-3-one
KW - Complete active space multiconfiguration SCF (CAS-SCF)
KW - Configuration interaction (CI-S)
KW - CS INDO CI
KW - Curcuminoid
KW - Density functional theory (DFT)
KW - Electronic excited states optimization
KW - Time-dependent SCF (TD-SCF)
UR - http://www.scopus.com/inward/record.url?scp=84962393581&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84962393581&partnerID=8YFLogxK
U2 - 10.1007/s00214-009-0604-2
DO - 10.1007/s00214-009-0604-2
M3 - Article
VL - 124
SP - 235
EP - 250
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
SN - 1432-881X
IS - 3-4
ER -