Synthesis, characterization and electrochemistry of phthalocyanine derivatives with biomedical applications

[摘要] English: A series of metal-free phthalocyanines, with ethylene glycol and alkyl peripheral and nonperipheralsubstituents, were synthesized and characterized with the aid of 1H NMR, IR andUV/vis spectroscopy. The electrochemical study (cyclic voltammetry) showed smaller peakpotentials for phthalocyanines with shorter ethylene glycol substituents, thus the shorter theethylene glycol chain, the higher the electron density of the macrocycle.Electrochemical (cyclic, square wave and linear sweep voltammetry) and computational(including the determination of relevant geometries and molecular orbitals) studies were doneon a series of ruthenium phthalocyaninato complexes. A comparison of the peak oxidationpotential of the first experimental oxidation process and computed energy of the highestoccupied molecular orbitals (HOMO) for the series of (CO)RuPc, showed a linearcorrelation..An RC1 reactor was used to study the hydrogenation reaction of 4-nitrophthalonitrile as weakas the oxidation reaction of 2,5-dihexylthiophene and 2,5didodecylthiophene utilizingdimethyldioxirane of oxidizing agent. By making use of the RC1 reactor, the reactions werefollowed kinetically and thermodynamically, yielding rate constants as well as reactionenthalpies. These results were compared to theoretical reaction enthalpies determined by DFTcalculations. Good correlation was found between the experimentally obtained reactionenthalpies and theoretical reaction enthalpies.

[发布机构] University of the Free State