meso-Tetra[2-(8-hydroxyquinolyl)]porphine was synthesized by the Rothemund method as a model of porphyrin with metal chelating groups in the peripheral region. The compound was soluble in dimethylformamide (DMF) but practically insoluble in water. Addition of Cu(II) perchlorate to the DMF solution resulted in biphasic spectral changes, an instantaneous change and a subsequent slow change. The spectrum after the first step showed the formation of the free base porphyrin with metal-chelated 8-quinolinol moieties. The second step was observable in the presence of a large excess of Cu(II) and was ascribed to the formation of the Cu(II)-porphyrin with Cu(II)-chelated 8-quinolinol. Addition of perchloric acid to the solution of the metalloporphyrin gave rise to the spectrum assignable to the Cu(II)-porphyrin with unchelated 8-quinolinol.
ASJC Scopus subject areas
- Drug Discovery