Synthesis of 3,6-bis(dialkylamino)substituted phthalonitriles

Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Helena Buršíková Supervisor doc. PharmDr. Miroslav Miletín, Ph.D. Consultant PharmDr. Veronika Nováková, Ph.D. Title of Thesis Synthesis of 3,6-bis(dialkylamino)substituted phthalonitriles Phthalonitriles are used as precursors for the synthesis of phthalocyanines (Pc). Pc are planar macrocyclic compounds with unique absorption and photophysical properties, for which they are used in many different fields. Capability to absorb light in range 630-800 nm and following production of ROS and singlet oxygen, both fundamental for principle of PDT, is essential for their biological applications. Non-peripheral substitution of Pc core by appropriate substituents was found to assure monomerization of Pc and cause the shift of the absorption band to higher wavelengths. Therefore, the diploma thesis is focused on the synthesis of phthalonitriles substituted in 3,6 positions by alkylamines, that are potentially suitable for the cyclotetramerization to the final non-peripherally substituted Pcs. Synthesis of required precursor was carried out in several different pathways. In the first case, nucleophilic substitutions of phthalonitriles derivatives 3,6-disubstituted..