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Synthesis and characterisation of advanced molecules with implemented adamantane skeleton
Jančík, Ján ; Maier,, Lukáš (referee) ; Krajčovič, Jozef (advisor)
This diploma thesis describes synthetic approach and characterization of advanced molecules with implemented adamantane skeleton and perspective use in attractive field of organic electronics. Three of four prepared molecules based on para-bis(2-thienyl)phenylene are original and totally new, and there were performed different synthetic approaches with comparison of yield, ecological and financial impact. Study of microwave synthetic approach was provided for cross-coupling reactions on para-bis(2-thienyl)phenylene skeleton. For all molecules were used ethyladamantyl and methyladamantyl substituents. Also, two completely new molecules based on 2,2':5',2''-terthiophene with ethyladamantyl and methyladamantyl substituents were prepared. In the next part were prepared new dimer structures of adamantane with possible application on field of polymers as bridge molecules. In the thesis were also made series of experiments for preparation of tetrasubstituted adamantane molecules, and for optimisation of preparation of spiroadamantane systems.
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Study of Thiophene Oligo-copolymers: Synthesis and Optoelectronic Properties
Krajčovič, Jozef ; Mazal,, Ctibor (referee) ; Kapička, Vratislav (referee) ; Friedl, Zdeněk (advisor)
Thesis presents synthesis and study of thiophene monomers, oligomers and polymers. The new series of thieno[3,4-b]pyrazine copolymers based on 3-dodecylthiophene and pyrazine monomers were prepared by oxidative polymerization with FeCl3. The effective synthetic method for preparation of 3-alkylthiophenes and thiophene oligomers was developed by optimizing of Kumada cross-couplig. The mentioned method could be realized for multikilos scale with possibility of transfer to pilot plant production. The second part of thesis focuses on synthesis and study of new thiophene compounds, which consist of both 2,3-diazo-1,3-butadiene bridge with two terminal chromophores and two thiophene units linked together via -position by pyrazine or hydrazine bridge. Finally, the new type of regular alternating copolymer consists of 2,2´:5´,2´´-terthiophene-5,5´-dicarboxylic acid (TEDA) and polyethyleneoxide (PEO) was prepared. Formation of polymer nano-subunits as separated phases in solid state was confirmed by TEM.
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The synthesis and functionalization of diketopyrrolopyrrole derivatives for organic electronics
Mamleev, Kamil ; Halaksa, Roman (referee) ; Krajčovič, Jozef (advisor)
Nowadays, organic electronics is a promising field of science. Because of a number of advantages, materials based on organic substances can replace existing inorganic analogues in such devices as organic solar cells, OLED, OFET, biosensors, etc. In the theoretical part of the bachelor's thesis, the molecules of diketopyrrolopyrrole (DPP), dithioketopyrrolopyrrole (DTPP), and their derivatives were fully reviewed. An overview of the synthesis and the properties of the derivatives of these molecules was given. Possible applications of DPP and DTPP in various areas of organic electronics were provided. The experimental part of the bachelor's thesis described the synthesis of DTPP structures with thiophene and phenyl substituents. In addition, a modification of thiophene DTPP with S'S alkylation was demonstrated. All synthesized compounds were purified by silica gel column chromatography. The structures of the obtained products were characterized by 1H NMR spectroscopy.
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Synthesis and studies of novel difuranone heterocycles for optoelectronic applications
Szotkowski, Martin ; Ing. Jan Vyňuchal, Ph.D (referee) ; Krajčovič, Jozef (advisor)
Organic electronics is a progressive field of science that combines knowledge of many disciplines concerned with the study and application possibilities of organic molecules from both, the low-molecular segment as well as the oligomers and polymers. Such molecules are well recognizable by their excellent properties and variability of their structure. This thesis deals with properties, applications and brief research review of benzodifuranones and diketopyrrolopyrroles as the representatives of smart molecules. Furthermore various synthetic approaches to the preparation of both symmetrical and unsymmetrical benzodifuranones are described. Experimental part is focused on the development of hydroxy(thiophene-2-yl) acetic acid initial intermediate for the development of benzodifuranone analogues containing aromatic thiophene core.
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Bio-inspired materials for aplications in organic electronics
Meindl, Jiří ; Pospíšilík, Karel (referee) ; Krajčovič, Jozef (advisor)
The bachelor ‘s thesis is a literary research, which summarise perspective bioinspired materials for organic electronic applications. Mainly focused are bioinspired and biocompatible materials in this thesis. The main area of interest is synthesis, characterization and application of these semiconducting materials. The first part of the thesis is focused on indigo, 6,6‘-dibromoindigo and thiophen derivatives of isoindigo copolymers. The second part of the thesis is all about biocompatible materials and applications of these materials in bio-protonic electronics. Malein-chitosan is described in this part as role model substance of bio-protonic electronics.
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IMPLEMETATION OF POLYCYCLIC SATURATED SYSTEMS IN ADVANCED SMART MOLECULES USABLE IN ORGANIC ELECTRONICS
Jančík, Ján ; Richtár, Jan (referee) ; Krajčovič, Jozef (advisor)
This essay deals with implementation of polycyclic saturated systems as bulky and very stable molecules, in advanced systems usable in organic electronics. It deals with theoretical aspects of structure and properties of polycyclic saturated systems, which based on available examples and literature are very perspective. Based on theoretical aspect in the first part of essay, the second part deals with synthesis of new molecule with incorporation of polycyclic saturated system usable in organic electronics. This part deals with all main intermediates synthetized via cross-coupling reactions.
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Study of effect of side chains of organic semiconductors for bioelectronic applications
Ivanová, Lucia ; Cigánek, Martin (referee) ; Krajčovič, Jozef (advisor)
Organic bioelectronics is a relatively young but perspective science discipline that introduces the applicability of organic electronic materials in bioelectronic devices. The promising outlook for using these applications ranges from improving the quality of the disabled people's life to the development of artificial intelligence. The theoretical part describes the essential properties of semiconducting polymers for the utilization in bioelectronics and, moreover, it presents a way of improving these properties by the proper implementation of the side chains. It deals with the possibility of optimizing the biomimetic properties of conjugated polymers by using bio-inspired molecules as peripheral chains, specifically nucleic bases. The nucleobase groups introduced onto the polymer chain thus provide the synthetic molecules with the ability of self-assembly and recognition of each other. The second part of the thesis focuses on the modification of the adenine molecule, with the preparation of the key intermediate for Stille coupling. Subsequent cross-coupling reaction results in the extension of the adenine’s -conjugated system with the thiophene molecule.
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Preparation and study of the reactivity of a new series of N, N'-substituted diketopyrrolopyrrole (DPP) for organic photonics
Cigánek, Martin ; Vyňuchal, Jan (referee) ; Krajčovič, Jozef (advisor)
Currently, the major trend is the development of materials that could be used for transformation of solar energy into electrical energy. Organic photovoltaics studies this area of interest and especially in recent years increasingly tries to put functional materials of organic origin into practice. These materials belong to a group of "high performance pigments" due to their exceptional and relatively stable properties. One of the most important molecules are the diketopyrrolopyrroles (DPP) derivatives. The theoretical part of this bachelor work describes the organic electronics and photonics, DPP derivatives, various synthetic routes of DPP, properties of particular DPP derivatives and the dependence of their properties on the used substituents. There are described separation and analytical methods most commonly used in organic synthesis too. The experimental part describes the preparation of the backbone DPP containing thiophene units. The following are the modifications of DPP backbones with N,N‘-alkylation and N,N‘-arylation.
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Synthesis of advanced adamantane containing intermediates based on para-bis (2-thienyl) phenylene. Influence of intramolecular hydrogen bonds on photoisomerization
Veselý, Dominik ; Pospíšilík, Karel (referee) ; Krajčovič, Jozef (advisor)
This diploma thesis describes study and onward synthesis of advanced organic structures with potential application in the field of organic electronics and, in particular, molecular photoswitches. In the theoretical part of the thesis are closely described most commonly used conventional molecular photoswitches with special attention to the influence of the structural modifications on properties and applications of the given derivatives. Next passage is dedicated to study of donor-acceptor systems, as fundamental building blocks for synthesis of advanced derivatives. The possibilities of derivatization with a goal of improving the physicochemical properties of these compounds are also discussed. In the final chapter are proposed modern synthetic methods for preparation of novel materials for organic electronics. This section is connected with an experimental part, where are designed and consequently synthesised 4 novel imine derivatives with dodecyl and adamantyl-ethyl side chain.
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