Synthesis and Acid-Base Properties of Tetraphenylporphine Derivatives with Amino Acid “Anchor” Groups

Abstract

Asymmetrically substituted 5,10,15,20-tetraphenylporphyrin derivatives such as 5-(4-aminophenyl)10,15,20-triphenylporphine, 5-[4-(tyrosinylamino)phenyl]-10,15,20-triphenylporphine and 5-{4-[( N - tert -butoxycarbonyltyrosinyl)amino]phenyl}-10,15,20-triphenylporphine were synthesized. Their spectral and acid-base properties were studied. The acid-base interactions of the obtained compounds in the binary acetonitrile–perchloric acid and dimethyl sulfoxide–potassium cryptate (KOH[222]) systems were studied by spectrophotometry method. The effect of the nature of the solvent, concentration, pH value on the chemical activity of porphyrin was analyzed. Amino acid fragments affect the protolytic equilibrium of porphyrins in acidic and basic media.