Synthesis, characterization and electrochemistry of phthalocyanine derivatives with biomedical applications

English: A series of metal-free phthalocyanines, with ethylene glycol and alkyl peripheral and nonperipheral substituents, were synthesized and characterized with the aid of 1H NMR, IR and UV/vis spectroscopy. The electrochemical study (cyclic voltammetry) showed smaller peak potentials for phthalocyanines with shorter ethylene glycol substituents, thus the shorter the ethylene 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 done on a series of ruthenium phthalocyaninato complexes. A comparison of the peak oxidation potential of the first experimental oxidation process and computed energy of the highest occupied molecular orbitals (HOMO) for the series of (CO)RuPc, showed a linear correlation.. An RC1 reactor was used to study the hydrogenation reaction of 4-nitrophthalonitrile as weak as the oxidation reaction of 2,5-dihexylthiophene and 2,5didodecylthiophene utilizing dimethyldioxirane of oxidizing agent. By making use of the RC1 reactor, the reactions were followed kinetically and thermodynamically, yielding rate constants as well as reaction enthalpies. These results were compared to theoretical reaction enthalpies determined by DFT calculations. Good correlation was found between the experimentally obtained reaction enthalpies and theoretical reaction enthalpies.