1. Metalation effect (M= Cu(II), Zn(II)) of bixin isolated from annato seeds (Bixa orellana L.) towards electronic transition in solvents.
- Author
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Silalahi, Imelda Hotmarisi, Rahmalia, Winda, Naselia, Uray Amira, and Usman, Thamrin
- Subjects
COPPER ,METALATION ,THIN layer chromatography ,POLAR solvents ,REFRACTIVE index ,APROTIC solvents ,SOLVENTS - Abstract
Bixin isolated from annatto seeds (Bixa Orellana L.) was metalated (M = Cu
2+ , Zn2+ ) through a reaction with the metal precursors in acetone under reflux conditions. The reaction was followed by thin layer chromatography showing that the metalation with copper(II) ion increases the polarity of the compound while metalation with zinc(II) appears to lower the polarity compared with the bixin alone. The UV-vis spectroscopy indicated that copper(II) metalation destabilize the ground state of π-π* system in the bixin structure demonstrated from the batochromic shift of the main transition band. Conversely zinc(II) metalation appears to stabilize the electronic density in the bixin molecule and shift the band towards higher electronic transition energy. Behavior of the bixin in aprotic polar solvents in association with the electronic transition energy appears to be maintained after metalation however copper(II) metalation enhances the polar solvents effects while zinc(II) metalation suggests the stabilization of π-π* system in non-polar solvents. Hansen solubility parameter and Onsager cavity model suggests that the electronic transition energy of the main band, S0 →S2 , in metalated-bixin depends on polarizability factor as the function of solvent refractive index, R(n2 ), and dispersion interactions, δD , but it is independent towards permanent dipole, δP , and hydrogen bonding, δH , interactions of solvents. [ABSTRACT FROM AUTHOR]- Published
- 2024
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