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The synthesis and study of new derivatives of diketopyrrolopyrroles for organic electronics
Cigánek, Martin ; Maier, Lukáš (referee) ; Krajčovič, Jozef (advisor)
This diploma thesis describes organic pigments of diketopyrrolopyrroles (DDPs) possessing properties applicable in attractive and perspective areas of organic electronics and photonics. The modification of the DPP skeleton was performed by nucleophilic substitution by various alkyl chains and 5 series of DPP derivatives were prepared. The regioselectivity of N-alkylation and also the photophysical properties of the prepared derivatives were studied. A key product of this work is the N,N'-ethyladamantyl derivative of DPP, which exhibited ambipolar characteristic with excellent electron mobility of 0.2 cm2 V–1 s–1. Further, the -conjugation of the above-mentioned DPP derivative was extended by 1 and 2 thiophene units at positions 3,6 and the effect of this modification on optical properties of the resulting derivatives was investigated. A new modified N,N'-unsubstituted DPP derivative was also prepared. The last point of this thesis was the study of the incorporation of formyl functional groups into the skeleton of key N,N'-ethyladamantyl DPP derivative.
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Complex identification of N-methylation reaction products in the synthesis of selected pharmaceuticals
Malíková, Sára ; Klusoň, Petr (advisor) ; Cuřínová, Petra (referee)
This thesis studied the process of the N-alkylation reaction of an ergoline derivative in a flow-through microreactor using phase transfer catalysis, which provides a faster exchange of substances at the phase interface and thus accelerates the reaction. Specifically, this reaction involved the N-methylation of LUME (10--methoxy-dihydrolysergic acid methyl ester) to the product MeLUME (1-methyl 10--methoxydihydrolysergic acid methyl ester). Dimethyl sulfate served as the alkylating agent and tetraethylammonium hydroxide as the phase transfer catalyst. Several side products are formed during this reaction. These are mainly LUME acid, which is formed by hydrolysis of the starting substance LUME, as well as the quaternary ammonium salt of the starting substance and the quaternary ammonium salt of the reaction product (MeLUME), which is formed by quaternization of the ergoline skeleton nitrogen due to used excess of the alkylating agent. The aim of this work was to develop an analytical method for the quantitative determination of the starting substance LUME and the products of the investigated N-alkylation reaction, including the most important side products. For this purpose, it was necessary to selectively prepare the above-mentioned side products and, on this basis, to determine their reaction...
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The synthesis and study of new derivatives of diketopyrrolopyrroles for organic electronics
Cigánek, Martin ; Maier, Lukáš (referee) ; Krajčovič, Jozef (advisor)
This diploma thesis describes organic pigments of diketopyrrolopyrroles (DDPs) possessing properties applicable in attractive and perspective areas of organic electronics and photonics. The modification of the DPP skeleton was performed by nucleophilic substitution by various alkyl chains and 5 series of DPP derivatives were prepared. The regioselectivity of N-alkylation and also the photophysical properties of the prepared derivatives were studied. A key product of this work is the N,N'-ethyladamantyl derivative of DPP, which exhibited ambipolar characteristic with excellent electron mobility of 0.2 cm2 V–1 s–1. Further, the -conjugation of the above-mentioned DPP derivative was extended by 1 and 2 thiophene units at positions 3,6 and the effect of this modification on optical properties of the resulting derivatives was investigated. A new modified N,N'-unsubstituted DPP derivative was also prepared. The last point of this thesis was the study of the incorporation of formyl functional groups into the skeleton of key N,N'-ethyladamantyl DPP derivative.
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