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Synthesis and Density Functional Theory Studies of Octakis(propyl)porphyrazine and its Zn(II) Complex

M.K. Mongale1, D.A. Isabirye1,*, M.M. Kabanda2, T.O. Aiyelabola1,3 and E.E. Ebenso2

1Department of Chemistry, School of Mathematical and Physical Sciences, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa

2Material Science Innovation & Modelling (MaSIM) Research Focus Area, Faculty of Agriculture, Science and Technology, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa

3Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria

*Corresponding author: E-mail: david.isabirye@nwu.ac.za

Abstract

Metalloporphyrazine 2,3,7,8,12,13,17,18-octakis(propyl)porphyrazine Zn(II) was synthesized and characterized using elemental analysis, IR, 1H NMR and UV-visible spectroscopy. The kinetics of the incorporation of Zn(II) into the free base 2,3,7,8,12,13,17,18-octakis(propyl) porphyrazine was also investigated. Quantum chemical calculations (utilizing B3LYP/6-31G(d,p) method) was carried out on the free base and its Zn(II) complex to determine their electronic and geometric properties. Time-dependent Density Functional theory (TDDFT) approach was utilized for the analysis of the UV-visible spectra. The results indicated that both the experimental and theoretical results were in reasonable agreement. This showed that metallation and alkylation respectively had significant influence on the molecular and electronic properties of the porphyrazine moiety. It was proposed that the peripheral substituent, cavity size and the size of the metal ion incorporated are the main factors that determine metallation rate and consequently reactivity of the metalloporphyrazine complex.

Keywords

Porphyrazine derivatives, Alkylation, Metalloporphyrazine, Macrocyclization, Mulliken atomic charges.

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