Azaphthalocyanines substituted with one aminogroup - influence of aliphatic substituents on intramolecular charge transfer.

CHARLES UNIVERSITY IN PRAGUE FACULTY OF PHARMACY IN HRADEC KRALOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND DRUG CONTROL Name: Ivana Zajícová Supervisor: Doc. PharmDr. Petr Zimčík Ph.D Azaphthalocyanines substituted with one aminogroup-influence of aliphatic substituents on intramolecular charge transfer. At the beginning of my thesis I was working on synthesis of 1,2,6,7,11,12,16,17- octakis-[(4-dimethylamino)benzylidenamino] porphyrazine from N,N-bis[(4- dimethylamino)benzylidenamino]fumaronitrile and N,N-bis[(4-dimethylamino) benzylidenamino]maleonitrile. Cyclotetramerization was performed with magnesium butoxide, zinc acetate in quinoline or in N, N-dimethylformamide. Unfortunately, no product was obtained. As an alternative aim, I started to deal with synthesis of unsymmetrical azaphthalocyanines substituted with one amino group. The amino group is a donor in intramolecular charge transfer. This process competes with fluorescence and singlet oxygen formation and may lead to compounds useful as dark quenchers of fluorescence in hybridization probes. I prepared a precursors, substituted pyrazine-2,3-dicarbonitriles, containing primary amino group, diethylamino- or butylamino- group. Prepared precursors were cyclotetramerized by method of statistical condensation. Cyclotetramerization was carried out in..