Azaphthalocyanines substituted with one aminogroup - distance dependence on photoinduced electron transfer

Charles University in Prague, Faculty of Pharmacy in Hradec Kralove Department: Department of Pharmaceutical Chemistry and Drug Control Candidate: Veronika Krepsova Supervisor: doc. PharmDr. Petr Zimcik, Ph.D. Title of Diploma Thesis: Azaphthalocyanines substituted with one aminogroup - distance dependence on photoinduced electron transfer Azaphthalocyanines (AzaPc), the aza-analogues of phthalocyanines are macrocyclic compounds with large conjugated system and mostly with high quantum yields of singlet oxygen and fluorescence. Intramolecular charge transfer (ICT) was discovered to proceed in AzaPc when alkylamino group is present on AzaPc periphery. ICT is responsible for quenching of excited states causing disappearance of singlet oxygen production and fluorescence emission. The aim of this thesis was to synthesize AzaPcs suitable for studying a similar process called photo-induced electron transfer (PET). In this process donor amino group is not in conjugation with AzaPc macrocycle, electron must "jump" over a distance leading to the quenching of excited states of molecules. In the first part of my work 5-chloro-6-methylpyrazine-2,3-dicarbonitrile was synthesized using nucleophilic substitution on 5-[2-(diethylamino)ethylsulfanyl]-6- methylpyrazine-2,3-dicarbonitrile (precursor A). The synthesis...