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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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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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Modification of Organic High Performance Pigments for Applications in Organic Electronics
Cigánek, Martin ; Imramovský, Aleš (referee) ; Vyňuchal, Jan (referee) ; Krajčovič, Jozef (advisor)
Dizertační práce pojednává o studiu, syntéze a chemické derivatizaci molekul spadajících do skupiny organických vysoce výkonných pigmentů a jejich potenciálním uplatnění v oblastech organické elektroniky. Teoretická část práce je zaměřena na nejnovější trendy v dané oblasti, a to jak z aplikačního potenciálu konkrétních derivátů, tak z pohledu syntetických možností a jejich strukturálních derivatizací. V experimentální části je pak podrobně popsána příprava pestré škály intermediátů a výsledných produktů, zahrnujících deriváty diketopyrrolopyrrolů (DPP), benzodifuranonu (BDF), epindolidionu (EP), naphthyridinedionu (NTD) a polymeru na bázi thiofenu (PT). Celkově bylo nasyntetizováno 103 molekul, přičemž 49 tvořily výsledné produkty, z nichž 27 bylo zcela nových, dosud nepublikovaných. Hlavním motivem derivatizace molekul pigmentů je zde inkorporace derivátů adamantanu do finálních struktur. V další části práce jsou blíže diskutovány jednotlivé chemické modifikace vedoucí k výsledným produktům. Na sérii N,N'-; N,O'- a O,O'-substituovaných derivátů DPP je popsána komplexní studie vlivu charakteru alkylových řetězců a také pozice jejich navázání v molekule DPP, a to nejen na selektivitu reakce, ale rovněž na optické i termické vlastnosti syntetizovaných produktů.
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Modification of Polyethylene by Reactive Compounding
Horkel, Ondřej ; Kučera, Jaroslav (referee) ; Petrůj, Jaroslav (advisor)
This Master’s thesis deals with the problematics of radically initiated compounding of polyethylene by 1-vinyladamantane. Theoretical part focuses on the theory of grafting processes and how they are influenced by chosen process parameters, as well as the properties of used monomer. In experimental part, two sets of experiments were designed, in both cases the chemicals used were polyethylene LITEN MB 87, (2,5-dimethyl-2,5-bis(tert-butylperoxy) hexane), also called Trigonox 101, as the initiator, and chemicals called Ionol and Irgafos 168 as stabilizers. The experiments were carried out in a Brabender batch mixer, the temperature was 180 – 185 °C, the reaction time was 5 minutes. The analytic methods used to evaluate the prepared samples’ properties were the tensile testing, the Charpy notch test, measuring of the melt flow index, analyzing the torque during kneading and the analysis of infrared spectra of the samples. By carrying out of these experiments it was found that excessive crosslinking was present with mass fraction of initiator being as low as 2 %. It was also concluded that under these conditions the modification does not improve tensile properties of the material, but it does improve the impact strength, albeit slightly. The influence of the modification on flow properties needs to be investigated further. A presence of vinyl groups was observed in infrared spectra, suggesting the presence of ungrafted vinyladamantane.
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Modification of Polypropylene by Reactive Compounding
Svítil, Jan ; Kučera, Jaroslav (referee) ; Petrůj, Jaroslav (advisor)
Knowledge of radical initiated grafting was summarized in theoretical part. It also contains a part about adamantane, its derivatives and a study of their use in polymer chemistry. In experimental part radical grafted polypropylene was prepared in batch mixer Brabender at 185 and 195 °C, 40 RPM and reaction time 5 min. Initiator 2,5-dimethyl-2,5-bis(tert-buthylperoxy)hexane (Trigonox 101) in concentrations between 0,2 – 4 wt % was used. 1-vinyladamantane was chosen as a monomer and its concetration ranged from 0,75 to 2,24 wt %. Mechanical properties of prepared samples were tested. Sample with content of initiator 0,2 wt % and monomer 1,4 wt % showed increase in notch toughness by 56,3 %, strength by 8,7 %, ductility by 11,5 % and decrease in MFR (230 °C; 2,16 kg) by 29,7 %. Values of torque indicated grafting reactions which couldn’t be proven by use of FTIR method so more suitable methods have been proposed.
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New derivatives of diketopyrrolo[2,3-f]indole (DPIs) for organic electronics
Šípek, Jiří ; Richtár, Jan (referee) ; Cigánek, Martin (advisor)
This bachelor's thesis deals with semiconducting materials based on diketopyrroloindoles, their preparation and possible applications. In the theoretical part of the thesis, a current overview of the issues of organic electronics and photonics is presented, and technologies using the potential of organic molecules to behave as semiconductors capable of transmitting electrical energy are presented. A brief history highlights important milestones for organic conductive molecules and polymers, including important categories of high performance organic pigments and dyes such as diketopyrroloindoles (DPI). In other parts of the work, the synthetic approaches known so far in the preparation of DPI themselves are summarized, with a focus on their thiophene analogues and related derivatives. In the experimental part, the preparation of the basic molecule of the DPI skeleton is described. Finally, three derivatives differing in the character of the aliphatic side chain from a series of branched, linear and bulky substituents prepared by means of N,N'alkylation reactions are presented.
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Implementation of polycyclic saturated systems in synthesis of advanced organic and hybrid materials for application in organic electronics
Jančík, Ján ; Částková, Klára (referee) ; Todorov, Petar (referee) ; Krajčovič, Jozef (advisor)
Ve všech oblastech současného průmyslu zažívají pokročilé materiály extrémní romzmach, a to díky neustálé miniaturizaci součástek a elektroniky, vytváření chytrých a funkčních materiálů, vývoji nových terapeutických a diagnostických metod a v neposlední řadě zdokonalování a zefektivňování výrobních procesů. Významné postavení v tomto systému má sektor organické elektroniky, ve kterém řada technologických firem a investorů vidí velkou budoucnost. K prokázání flexibility, všestrannosti a škálovatelnosti pokročilých materiálů byly syntetizované a zkumané zcela nové adamantanem substituované polythiofeny. Tyto polymery jako silné konkurenty komerčně využívaných materiálů ukazují, že oblast organické elektroniky dosud nedosáhla svých hranic. Byla provedena rozsáhlá charakterizace a studium nových polymerů. Pro rozšíření záběru výzkumu byla navržena, připravena a zkoumána řada zcela nových fotospfotospínačů na bázi para-bis(2-thienyl)fenylenu jako dalšího typu pokročilých organických materiálů. Podle aktuálních trendů byly zkoumány i perovskitové materiály. Byla vyvinuta a optimalizována zcela nová, k životnímu prostředí šetrná, nízkonákladová a snadno do velkovýroby tranformovatelná metoda pro přípravu čtyř nejčastěji používaných hybridních perovskitových makrokrystalů. Tato metoda by mohla být odpovědí pro průmyslovou výrobu vysoce kvalitních, bezchybných a symetrických perovskitových krystalů a zařízení. Na druhou stranu byly zkoumány různé druhy perovskitových nanočástic za účelem zlepšení stability a vlastností. Byla zkoumána základní stabilizace za pomocí ligandů se zaměřením na ligandy na bázi adamantanu a pro zlepšení vlastností byla navržena stabilizace za pomocí polymerní matrice. Jako vodivá matrice pro perovskitové nanočástice byly použity adamantylem substituované polythiofeny ve formě tenkých vrstev.
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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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Modification of Polypropylene by Reactive Compounding
Svítil, Jan ; Kučera, Jaroslav (referee) ; Petrůj, Jaroslav (advisor)
Knowledge of radical initiated grafting was summarized in theoretical part. It also contains a part about adamantane, its derivatives and a study of their use in polymer chemistry. In experimental part radical grafted polypropylene was prepared in batch mixer Brabender at 185 and 195 °C, 40 RPM and reaction time 5 min. Initiator 2,5-dimethyl-2,5-bis(tert-buthylperoxy)hexane (Trigonox 101) in concentrations between 0,2 – 4 wt % was used. 1-vinyladamantane was chosen as a monomer and its concetration ranged from 0,75 to 2,24 wt %. Mechanical properties of prepared samples were tested. Sample with content of initiator 0,2 wt % and monomer 1,4 wt % showed increase in notch toughness by 56,3 %, strength by 8,7 %, ductility by 11,5 % and decrease in MFR (230 °C; 2,16 kg) by 29,7 %. Values of torque indicated grafting reactions which couldn’t be proven by use of FTIR method so more suitable methods have been proposed.
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Modification of Polyethylene by Reactive Compounding
Horkel, Ondřej ; Kučera, Jaroslav (referee) ; Petrůj, Jaroslav (advisor)
This Master’s thesis deals with the problematics of radically initiated compounding of polyethylene by 1-vinyladamantane. Theoretical part focuses on the theory of grafting processes and how they are influenced by chosen process parameters, as well as the properties of used monomer. In experimental part, two sets of experiments were designed, in both cases the chemicals used were polyethylene LITEN MB 87, (2,5-dimethyl-2,5-bis(tert-butylperoxy) hexane), also called Trigonox 101, as the initiator, and chemicals called Ionol and Irgafos 168 as stabilizers. The experiments were carried out in a Brabender batch mixer, the temperature was 180 – 185 °C, the reaction time was 5 minutes. The analytic methods used to evaluate the prepared samples’ properties were the tensile testing, the Charpy notch test, measuring of the melt flow index, analyzing the torque during kneading and the analysis of infrared spectra of the samples. By carrying out of these experiments it was found that excessive crosslinking was present with mass fraction of initiator being as low as 2 %. It was also concluded that under these conditions the modification does not improve tensile properties of the material, but it does improve the impact strength, albeit slightly. The influence of the modification on flow properties needs to be investigated further. A presence of vinyl groups was observed in infrared spectra, suggesting the presence of ungrafted vinyladamantane.
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