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Implementace polycyklických nasycených systémů do pokročilých „smart“ molekul využitelných v organické elektronice
Jančík, Ján ; Richtár, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
Tato práce pojednává o implementaci polycyklických nasycených systémů, jakožto objemných a velice stabilních molekul do pokročilých molekul využitelných v organické elektronice. Zabývá se teoretickými aspekty struktury a vlastností polycyklických nasycených systémů, které se na základě dosavadních výzkumů a odstupních příkladů z literatury ukazují velice perspektivní. Na základě získaných poznatků, je v druhé části práce popsána příprava úplně nové dosud nepopsané molekuly obsahující polycyklický nasycený systém vhodné pro organickou elektroniku. V této části jsou popsány také všechny klíčové intermediáty získané cross-kaplingovými reakcemi.
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Bio-inspirované uracilové stavební jednotky jako terminální skupiny pro elektronické materiály
Krusberský, Vojtěch ; Ivanová, Lucia (oponent) ; Richtár, Jan (vedoucí práce)
Tato bakalářská práce se zaměřuje na syntézu, purifikaci a charakterizaci bio-inspirovaných elektronakceptorních motivů v podobě N,N’-dialkylovaných derivátů barbiturové kyseliny pro potenciální aplikace v oblasti N-typových organických polovodičů. Teoretická část pojednává o organických polovodičích a principech jejich vodivosti, dále o uracilu, barbiturové kyselině a jejích derivátech a také o syntetických přístupech k cílovým molekulám práce a jejich analogům. V rámci experimentální části byly vybrány dva druhy alkylových substituentů – flexibilní butyl a objemný a rigidní adamantylethyl. Každý z nich byl do struktury inkorporován přes příslušnou symetrickou dialkylmočovinu, která byla následně podrobena kondenzační reakci na N,N’-dialkylbarbiturovou kyselinu. Finálním krokem byla Knoevenagelova kondenzace s -konjugovaným trimerem.
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Novel organic semiconductors for bioelectronic applications
Veselý, Dominik ; Richtár, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
This bachelor’s thesis deals with a highly perspective field of bioorganic electronics. It is divided into a theoretical and an experimental part. In the theoretical part of the thesis basic device functioning principles in conjunction with living organisms and production of such devices together with their practical application are elaborated on. In the next part of the thesis conductive polymers as advanced materials for organic electronics, their synthesis, chemical modification and functionalisation, but also their use for functional electronic devices are analysed. A synthetic route for preparation of new functional organic materials by the means of modification of a basic monomer on a molecular level is proposed in the final chapter. This chapter is connected with an experimental part where a basic monomer of the most important conductive polymer for bioelectronic applications is prepared.
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Synthesis and Characterization of New Organic Materials for Organic Electronics
Richtár, Jan ; Vícha,, Robert (oponent) ; Weidlich,, Tomáš (oponent) ; Krajčovič, Jozef (vedoucí práce)
In the modern era, organic electronics and bioelectronics go through tremendous development efforts to obtain novel organic materials with features usually unattainable by conventional silicon-based electronics. This thesis concerns the synthesis and characterization of novel organic materials for organic electronics. It deals with the synthesis of novel pentafluorosulfanylated heterocyclic building blocks, alkylated high-performance organic pigments, and bioinspired organic -conjugated materials with tunable physico-chemical properties and rational synthetic approaches towards their preparation. Pentafluorosulfanyl group (SF5) is appreciated for the high electronegativity, lipophilicity, thermal and chemical stability. It influences positively optical and electronic properties, solubility, and stability to a degree often superior to more established CF3-analogues. Two types of derivatives of 3-SF5-substituted pyrrolidines were synthesized by six and four-step synthetic approaches serving as potential versatile building blocks for the incorporation into advanced aromatic and heteroaromatic -conjugated systems via nitrogen atoms as the fluorinated terminal groups. A model derivative was introduced as a terminal group in an electron-deficient heteroaromatic system by nucleophilic substitution. Hydrogen-bonded high-performance organic pigments attract a lot of attention due to their impressive semiconducting properties, strong 2D molecular association, high thermal, chemical and photochemical stability, and non-toxicity. Nevertheless, they suffer from limited solubility and processability which is commonly solved by the introduction of solubilizing groups. Moreover, particularly bulky rigid adamantyl-bearing groups are known to improve molecular packing, thermal stability, and resulting properties due to the self-organizing ability of adamantane. The adamantylmethyl and adamantylethyl groups were incorporated into selected hydrogen-bonded dyes and pigments from groups of carbonyl azaacenes, rylene-diimides and indigoids by means of nucleophilic substitution aiming towards increasing solubility and processability while preserving the thermal stability and favorable solid-state molecular packing. Physico-chemical studies of quinacridone and epindolidione series showed thermal stability comparable or higher than for H-bonded derivatives, good solubility in organic solvents, strong fluorescence in solid state and solution in VIS region and distinct molecular packing in single crystals as was observed from X-ray analysis. Flavins are ubiquitous bio-inspired organic material with indispensable biological functions, promising physico-chemical properties, chemical and application versatility. Consequently, the focus was put on the tuning of the optical, electronic, electrochemical, thermal and other properties by the extension of the -conjugated system of said materials. Initially, two complementary synthetic approaches were envisaged in order to provide NH-free flavin series which was to undergo comprehensive physico-chemical studies. Afterwards, two different approaches were proposed to synthesize N,N’-dialkylated flavins incorporating butyl, adamantylethyl and triethyleneglycol-derived substituents. The alkylation enhanced solubility in organic solvents and aqueous media, increased fluorescence in solid state and solutions, and tuned the thermal properties depending on the alkyl substitution.
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The synthesis of organic -conjugated systems for advanced photonic applications
Prekopová, Terézia ; Richtár, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
This diploma thesis is focused on the synthesis of new, organic, -conjugated systems with potential use in the field of singlet fission (SF). It is one of the most efficient multiexciton generation processes studied so far, which offers the potential to increase the efficiency of solar cells. The theoretical part focuses on the description of SF and the molecules providing this phenomenon. The first aim of the experimental part is focused on the synthesis of target pentacene and anthracene derivatives. The work presents and verifies three synthetic approaches to the preparation of these molecules, of which only one has proven to be successful. The second aim deals with the synthesis of intermediates that are crucial for the preparation of target pyrene fused pyrazaacenes. The synthesis consists of the oxidation of pyrene and the condensation of 4,5-diketone or 4,5,9,10-tetraketone with commercially available diamines or diamines prepared by us. A basic optical characterization was performed on these derivatives, which showed the effect of substitution on excimer emission. Assuming the same quantum fluorescence yield for all molecules and comparing the spectral measurements, it was found that the solid phase excimer emission is significantly higher than in solution.
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Nové deriváty diketopyrrolo[2,3-f]indolu (DPI) pro organickou elektroniku
Šípek, Jiří ; Richtár, Jan (oponent) ; Cigánek, Martin (vedoucí práce)
Tato bakalářská práce pojednává o polovodivých materiálech na bázi diketopyrroloindolů, jejich přípravě a možné aplikaci. V teoretické části práce je představen současný náhled na problematiku organické elektroniky a fotoniky, dále jsou představeny technologie využívající potenciálu organických molekul chovat se jako polovodiče schopné přenosu elektrické energie. Stručnou historií jsou připomenuty milníky důležité pro organické vodivé molekuly a polymery, včetně představení důležité kategorie vysoce-výkonných organických pigmentů a barviv, jako jsou právě diketopyrroloindoly (DPI). V další částí této práce jsou shrnuty dosud známé syntetické přístupy v přípravě samotných DPI, se zaměřením na jejich thiofenové analogy a příbuzných derivátů. V experimentální části je pak popsána příprava základního skeletu molekuly DPI. Nakonec jsou představeny tři deriváty lišící se charakterem postranního alifatického řetězce ze série rozvětvených, lineárních a objemných substituentů připravených pomocí N,N‘alkylačních reakcí.
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Bio-inspirované uracilové stavební jednotky jako terminální skupiny pro elektronické materiály
Krusberský, Vojtěch ; Ivanová, Lucia (oponent) ; Richtár, Jan (vedoucí práce)
Tato bakalářská práce se zaměřuje na syntézu, purifikaci a charakterizaci bio-inspirovaných elektronakceptorních motivů v podobě N,N’-dialkylovaných derivátů barbiturové kyseliny pro potenciální aplikace v oblasti N-typových organických polovodičů. Teoretická část pojednává o organických polovodičích a principech jejich vodivosti, dále o uracilu, barbiturové kyselině a jejích derivátech a také o syntetických přístupech k cílovým molekulám práce a jejich analogům. V rámci experimentální části byly vybrány dva druhy alkylových substituentů – flexibilní butyl a objemný a rigidní adamantylethyl. Každý z nich byl do struktury inkorporován přes příslušnou symetrickou dialkylmočovinu, která byla následně podrobena kondenzační reakci na N,N’-dialkylbarbiturovou kyselinu. Finálním krokem byla Knoevenagelova kondenzace s -konjugovaným trimerem.
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The synthesis of organic -conjugated systems for advanced photonic applications
Prekopová, Terézia ; Richtár, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
This diploma thesis is focused on the synthesis of new, organic, -conjugated systems with potential use in the field of singlet fission (SF). It is one of the most efficient multiexciton generation processes studied so far, which offers the potential to increase the efficiency of solar cells. The theoretical part focuses on the description of SF and the molecules providing this phenomenon. The first aim of the experimental part is focused on the synthesis of target pentacene and anthracene derivatives. The work presents and verifies three synthetic approaches to the preparation of these molecules, of which only one has proven to be successful. The second aim deals with the synthesis of intermediates that are crucial for the preparation of target pyrene fused pyrazaacenes. The synthesis consists of the oxidation of pyrene and the condensation of 4,5-diketone or 4,5,9,10-tetraketone with commercially available diamines or diamines prepared by us. A basic optical characterization was performed on these derivatives, which showed the effect of substitution on excimer emission. Assuming the same quantum fluorescence yield for all molecules and comparing the spectral measurements, it was found that the solid phase excimer emission is significantly higher than in solution.
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Synthesis and Characterization of New Organic Materials for Organic Electronics
Richtár, Jan ; Vícha,, Robert (oponent) ; Weidlich,, Tomáš (oponent) ; Krajčovič, Jozef (vedoucí práce)
In the modern era, organic electronics and bioelectronics go through tremendous development efforts to obtain novel organic materials with features usually unattainable by conventional silicon-based electronics. This thesis concerns the synthesis and characterization of novel organic materials for organic electronics. It deals with the synthesis of novel pentafluorosulfanylated heterocyclic building blocks, alkylated high-performance organic pigments, and bioinspired organic -conjugated materials with tunable physico-chemical properties and rational synthetic approaches towards their preparation. Pentafluorosulfanyl group (SF5) is appreciated for the high electronegativity, lipophilicity, thermal and chemical stability. It influences positively optical and electronic properties, solubility, and stability to a degree often superior to more established CF3-analogues. Two types of derivatives of 3-SF5-substituted pyrrolidines were synthesized by six and four-step synthetic approaches serving as potential versatile building blocks for the incorporation into advanced aromatic and heteroaromatic -conjugated systems via nitrogen atoms as the fluorinated terminal groups. A model derivative was introduced as a terminal group in an electron-deficient heteroaromatic system by nucleophilic substitution. Hydrogen-bonded high-performance organic pigments attract a lot of attention due to their impressive semiconducting properties, strong 2D molecular association, high thermal, chemical and photochemical stability, and non-toxicity. Nevertheless, they suffer from limited solubility and processability which is commonly solved by the introduction of solubilizing groups. Moreover, particularly bulky rigid adamantyl-bearing groups are known to improve molecular packing, thermal stability, and resulting properties due to the self-organizing ability of adamantane. The adamantylmethyl and adamantylethyl groups were incorporated into selected hydrogen-bonded dyes and pigments from groups of carbonyl azaacenes, rylene-diimides and indigoids by means of nucleophilic substitution aiming towards increasing solubility and processability while preserving the thermal stability and favorable solid-state molecular packing. Physico-chemical studies of quinacridone and epindolidione series showed thermal stability comparable or higher than for H-bonded derivatives, good solubility in organic solvents, strong fluorescence in solid state and solution in VIS region and distinct molecular packing in single crystals as was observed from X-ray analysis. Flavins are ubiquitous bio-inspired organic material with indispensable biological functions, promising physico-chemical properties, chemical and application versatility. Consequently, the focus was put on the tuning of the optical, electronic, electrochemical, thermal and other properties by the extension of the -conjugated system of said materials. Initially, two complementary synthetic approaches were envisaged in order to provide NH-free flavin series which was to undergo comprehensive physico-chemical studies. Afterwards, two different approaches were proposed to synthesize N,N’-dialkylated flavins incorporating butyl, adamantylethyl and triethyleneglycol-derived substituents. The alkylation enhanced solubility in organic solvents and aqueous media, increased fluorescence in solid state and solutions, and tuned the thermal properties depending on the alkyl substitution.
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Novel organic semiconductors for bioelectronic applications
Veselý, Dominik ; Richtár, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
This bachelor’s thesis deals with a highly perspective field of bioorganic electronics. It is divided into a theoretical and an experimental part. In the theoretical part of the thesis basic device functioning principles in conjunction with living organisms and production of such devices together with their practical application are elaborated on. In the next part of the thesis conductive polymers as advanced materials for organic electronics, their synthesis, chemical modification and functionalisation, but also their use for functional electronic devices are analysed. A synthetic route for preparation of new functional organic materials by the means of modification of a basic monomer on a molecular level is proposed in the final chapter. This chapter is connected with an experimental part where a basic monomer of the most important conductive polymer for bioelectronic applications is prepared.
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