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The effect of substitution on the basicity of azomethine nitrogens of phthalocyanines
Ludvová, Lucie ; Nováková, Veronika (advisor) ; Miletín, Miroslav (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Chemistry and Drug Control Candidate: Mgr. Lucie Ludvová Supervisor: assoc. prof. PharmDr. Veronika Nováková, Ph.D. Title of Thesis: The effect of substitution on the basicity of azomethine nitrogens of phthalocyanines This work deals with the effect of substituents on the basicity of azomethine nitrogens in phthalocyanines, which are macrocyclic compounds with wide system of conjugation bounds. Substituents differed in their position at the macrocycle (attached at peripheral or non-peripheral positions) and in the type of substituents (alkylsulfanyl-, alkyloxy- or alkyl groups). Three zinc phthalocyanines were prepared in this project to complete the above mentioned series. In the first step, appropriate precursors were prepared by multi-step procedure using e.g. nucleophilic substitution or Negishi coupling reaction. These precursors were further used for cyclotetramerization reaction to get metal free phthalocyanines. Finally, the zinc cation was coordinated into the center of phthalocyanines. The second part of the project focused on the determination of the basicity of this series of zinc phthalocyanines by the mean of the absorption spectroscopy. The highest basicity showed...
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The effect of substitution on the basicity of azomethine nitrogens of phthalocyanines
Ludvová, Lucie ; Nováková, Veronika (advisor) ; Miletín, Miroslav (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Chemistry and Drug Control Candidate: Mgr. Lucie Ludvová Supervisor: assoc. prof. PharmDr. Veronika Nováková, Ph.D. Title of Thesis: The effect of substitution on the basicity of azomethine nitrogens of phthalocyanines This work deals with the effect of substituents on the basicity of azomethine nitrogens in phthalocyanines, which are macrocyclic compounds with wide system of conjugation bounds. Substituents differed in their position at the macrocycle (attached at peripheral or non-peripheral positions) and in the type of substituents (alkylsulfanyl-, alkyloxy- or alkyl groups). Three zinc phthalocyanines were prepared in this project to complete the above mentioned series. In the first step, appropriate precursors were prepared by multi-step procedure using e.g. nucleophilic substitution or Negishi coupling reaction. These precursors were further used for cyclotetramerization reaction to get metal free phthalocyanines. Finally, the zinc cation was coordinated into the center of phthalocyanines. The second part of the project focused on the determination of the basicity of this series of zinc phthalocyanines by the mean of the absorption spectroscopy. The highest basicity showed...
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Photophysical and Photochemical Study of Metal Free Phthalocyanines and Their Azaanalogues
Ludvová, Lucie ; Nováková, Veronika (advisor) ; Švec, Jan (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department: Department of Biophysics and Physical Chemistry Candidate: Lucie Ludvová Supervisor: PharmDr. Veronika Nováková, Ph.D. Title of Diploma Thesis: Photophysical and Photochemical Study of Metal Free Phthalocyanines and Their Azaanalogues This work deals with phthalocyanines and azaphthalocyanines that are macrocyclic compounds with large conjugated system giving them interesting photophysical properties. The aim of this work was to prepare new phthalocyanines and azaphthalocyanines and complete a previously prepared series of compounds. Concretely, the compounds with peripheral substituents connected through oxygen (tert-butoxy for azaphthalocyanines and butoxy and tert-butoxy for phthalocyanines) were intended to prepare. The work was mainly focused on the synthesis of intermediates (4,5-dibutoxyphthalonitrile and 4,5-di-tert-butoxyphthalonitrile), that are precursors for the preparation of phthalocyanines. 4,5-disubstituted phthalonitriles with a substituents bound through heterotom are usually synthesized using nucleophilic substitution of 4,5-dichlorophthalonitrile. However, this procedure was not successful in our case. The method was changed and 4,5-dibutoxyphthalonitrile was successfully prepared from pyrocatechol,...
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