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Synthesis of cationic phthalocyanines
Cidlina, Antonín ; Zimčík, Petr (advisor) ; Miletín, Miroslav (referee)
CHARLES UNIVERSITY IN PRAGUE FACULTY OF PHARMACY IN HRADEC KRÁLOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND DRUG CONTROL Author: Antonín Cidlina Supervisor: Assoc. Prof. PharmDr. Petr Zimčík PhD. Title: Synthesis of cationic phthalocyanines In my thesis, I dealt with the preparation of cationic phthalocyanines containing quaternary ammonium groups in peripheral chains that are attached to α or β positions of the macrocycle. The synthesis of precursors for cyclotetramerization was the first step of this work. They were prepared by nucleophilic substitution of aromatic dicarbonitriles by 2- (diethylamino)ethanthiolate. These precursors were used to cyclotetramerization in presence of magnesium butoxide. Magnesium phthalocyanines were prepared by this procedure. Magnesium complexes were converted to metal-free phthalocyanines in acidic medium. Then, they reacted with anhydrous zinc acetate to form zinc phthalocyanines. Subsequently, alkylation of peripheral amino groups by ethyliodide led to quaternized Pc. In addition, the derivates with substitution in α positions did not aggregate in aqueous media. Furthermore, zinc phtalocyanine substituted in α positions had very good photochemical properties. That is why it may become potential photosensitizer with promising photodynamic activity.
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Synthesis of cationic phthalocyanines
Cidlina, Antonín ; Zimčík, Petr (advisor) ; Miletín, Miroslav (referee)
CHARLES UNIVERSITY IN PRAGUE FACULTY OF PHARMACY IN HRADEC KRÁLOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND DRUG CONTROL Author: Antonín Cidlina Supervisor: Assoc. Prof. PharmDr. Petr Zimčík PhD. Title: Synthesis of cationic phthalocyanines In my thesis, I dealt with the preparation of cationic phthalocyanines containing quaternary ammonium groups in peripheral chains that are attached to α or β positions of the macrocycle. The synthesis of precursors for cyclotetramerization was the first step of this work. They were prepared by nucleophilic substitution of aromatic dicarbonitriles by 2- (diethylamino)ethanthiolate. These precursors were used to cyclotetramerization in presence of magnesium butoxide. Magnesium phthalocyanines were prepared by this procedure. Magnesium complexes were converted to metal-free phthalocyanines in acidic medium. Then, they reacted with anhydrous zinc acetate to form zinc phthalocyanines. Subsequently, alkylation of peripheral amino groups by ethyliodide led to quaternized Pc. In addition, the derivates with substitution in α positions did not aggregate in aqueous media. Furthermore, zinc phtalocyanine substituted in α positions had very good photochemical properties. That is why it may become potential photosensitizer with promising photodynamic activity.
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Influence of structural aspects on photophysical properties at phthalocyanines
Cidlina, Antonín ; Zimčík, Petr (advisor) ; Musílek, Kamil (referee) ; Lang, Kamil (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Chemistry and Drug Control Candidate: Mgr. Antonín Cidlina Supervisor: doc. PharmDr. Petr Zimčík, Ph.D. Consultant: doc. PharmDr. Veronika Nováková, Ph.D. Title of the Thesis: Influence of structural aspects on photophysical properties at phthalocyanines Phthalocynines (Pc) and their aza-analoues tetrapyrazinoporphyrazines (TPyzPz) are macrocyclic compounds with 18 delocalized π-electrons. The large conjugated system of double bonds imparts them unique spectral, photophysical and electronic properties which can be tuned by peripheral substitution or/and central metal cation. They found their use in several areas such as photodynamic therapy, catalyst, liquid crystals and solar cells. The first part of this doctoral thesis describes the influence of structural aspects on effectiveness of intramolecular charge transfer (ICT) at TPyzPz. ICT is responsible for considerable decrease of photophysical parameters of TPyzPz - quantum yields of singlet oxygen () and fluorescence (F). At first, we focused on the effect of the electronic properties of peripheral substituents attached on macrocycle core on ICT efficiency in TPyzPz. The series of TPyzPz with various peripheral substituents was designed and...
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Synthesis of cationic phthalocyanines
Cidlina, Antonín ; Zimčík, Petr (advisor) ; Miletín, Miroslav (referee)
CHARLES UNIVERSITY IN PRAGUE FACULTY OF PHARMACY IN HRADEC KRÁLOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND DRUG CONTROL Author: Antonín Cidlina Supervisor: Assoc. Prof. PharmDr. Petr Zimčík PhD. Title: Synthesis of cationic phthalocyanines In my thesis, I dealt with the preparation of cationic phthalocyanines containing quaternary ammonium groups in peripheral chains that are attached to α or β positions of the macrocycle. The synthesis of precursors for cyclotetramerization was the first step of this work. They were prepared by nucleophilic substitution of aromatic dicarbonitriles by 2- (diethylamino)ethanthiolate. These precursors were used to cyclotetramerization in presence of magnesium butoxide. Magnesium phthalocyanines were prepared by this procedure. Magnesium complexes were converted to metal-free phthalocyanines in acidic medium. Then, they reacted with anhydrous zinc acetate to form zinc phthalocyanines. Subsequently, alkylation of peripheral amino groups by ethyliodide led to quaternized Pc. In addition, the derivates with substitution in α positions did not aggregate in aqueous media. Furthermore, zinc phtalocyanine substituted in α positions had very good photochemical properties. That is why it may become potential photosensitizer with promising photodynamic activity.
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