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Nízkomolekulární materiály pro organickou elektroniku a fotoniku
Češka, Matěj ; Salyk, Ota (oponent) ; Weiter, Martin (vedoucí práce)
Tato diplomová práce je zaměřena na studium organických materiálů využitelných v oblasti elektroniky a fotoniky, přičemž pozornost byla věnována nízkomolekulárním látkám. Součástí práce je teoretická část, která obsahuje stručný úvod do organické elektroniky a fotoniky. Především zde byly zmíněny organické tranzistory, organické solární články a organické světlo emitující diody. Cílem experimentální části bylo studium elektrických a optických vlastností dvou druhů ftalocyaninů. Za tím účelem byly připraveny tenké vrstvy a roztoky ftalocyaninů, které byly charakterizovány metodou UV-VIS spektroskopie. Připravené tenké vrstvy byly také charakterizovány metodou volt-ampérových charakteristik, metodou spektrálně rozlišené fotovodivosti a metodou transientní fotovodivosti. Z výsledků vyplývá, že tenké vrstvy ftalocyaninů mění po vystavení světelnému záření své elektrické vlastnosti. Vlastnosti tenkých vrstev také závisely na druhu použitého ftalocyaninu a tloušťce vrstvy.
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Utilization of nanomaterials for organic electronic and photovoltaics
Flimel, Karol ; Žídek, Jan (oponent) ; Weiter, Martin (vedoucí práce)
The study of the new materials potentially usable for organic photovoltaic and electronics are getting very important from the point of ecological and financial view. Organic electronic devices are getting more and more popular and it is only up to us to search for the new ones that are able to improve their physical properties. The aim of this thesis is to search for materials like have been mentioned above which have very good semiconducting properties. Solutions of pure materials and its mixtures with different concentrations of fullerene have been investigated by ultra-violet spectroscopy, classical fluorescence and time resolved spectrometry. Mainly, were studied the influence of the central atom and side substituents for the optical and electronical properties of our materials of interest. With adding fullerene was observed quenching phenomena of the fluorescence, because all these new materials show usually high photoluminescence. Based on the given results, the most suitable materials had been chosen to provide trial of making organic solar cell, and therefore investigated by the mean of electric measurements (direct current).
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Organic materials for molecular electronics and photonics
Vrchotová, Jana ; Cimrová, Věra (oponent) ; Zmeškal, Oldřich (oponent) ; Weiter, Martin (vedoucí práce)
Organic electronics is a dynamic rapidly growing industry. Therefore the research of novel materials for organic electronics is an important challenge both in terms of materials performance and economy of the final product, while the environmental impact is also important. Diketopyrrolopyrrole derivatives are materials with a great potential for organic electronics exploitation. This thesis is focused on optical and electrical characterization of diketopyrrolopyrroles, an assessment of their potential applications in organic electronics and suggestions, how to optimize their performance. Theoretical part of this thesis describes state of art in organic electronics with focus on the field of diketopyrrolopyrrole based materials. Subsequent results part summarizes important results and contains brief introduction to the enclosed publications, including evaluation of author´s personal contribution to particular publications. Results part consists of 6 scientific articles, integral to this thesis, thematically connected with area of organic electronics, new diketopyrrolopyrrole based materials and their applications. Formally the thesis is, based on article 42 paragraph 1b of The Study and Examination Rules of BUT, designed as thematically arranged set of published works and works accepted for publication.
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Modification of Organic High Performance Pigments for Applications in Organic Electronics
Cigánek, Martin ; Imramovský, Aleš (oponent) ; Vyňuchal, Jan (oponent) ; Krajčovič, Jozef (vedoucí práce)
The doctoral thesis deals with the study, synthesis and chemical derivatization of molecules belonging to the group of organic high-performance pigments and their potential application in the fields of organic electronics. The theoretical part of the work is focused on the latest trends in the area mentioned above, both from the application potential of specific derivatives and in terms of synthetic possibilities and their structural derivatization. The experimental part describes in detail the preparation of a wide range of intermediates and final products, including derivatives of diketopyrrolopyrroles (DPP), benzodifuranone (BDF), epindolidione (EP), naphthyridinedione (NTD) and thiophene-based polymer (PT). A total of 103 molecules were synthesized, of which 49 were final products, and 27 of them were completely novel, as yet unpublished. Herein, the main motive for the derivatization of pigment molecules is the incorporation of bulky adamantyl substituents into the resulting derivative structures. In the next part of the work, individual chemical modifications leading to the final products are discussed in more detail. In the series of N,N'-; N,O'- and O,O'-substituted DPP derivatives, the influence of both the alkyl chains’ character and binding position in the DPP molecule on the selectivity of the reaction, the thermal and optical properties of the resulting derivatives is comprehensively described.
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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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Pokročilé materiály pro organickou bioelektroniku
Sedlák, Jiří ; Salyk, Ota (oponent) ; Weiter, Martin (vedoucí práce)
Tato bakalářská práce se zabývá zkoumáním materiálu PEDOT:DBSA pro možné využití v organické bioelektronice. Nejprve byl standardizován postup pro přípravu vrstev látky PEDOT:DBSA o požadované tloušťce a byla sledována závislost tloušťky na vodivost materiálu. Následně byl testován vliv teplotní stabilizace a látek EG, DMSO a H2SO4 na vodivost připravených vrstev. Pro zvýšení vodivosti byly testovány dva principy. Prvním byl princip přídavku látek jako dopantů do kapalných roztoků polymeru. Druhým způsobem přípravy vzorků byla metoda sekundárního ošetření již připravených vrstev čistého PEDOT:DBSA. Všechny připravené polymerní vrstvy byly charakterizovány pomocí čtyřbodové analýzy a profilometrie.
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Syntéza a studium nových derivátů diketopyrrolopyrrolů (DPPs) pro organickou elektroniku
Cigánek, Martin ; Maier, Lukáš (oponent) ; Krajčovič, Jozef (vedoucí práce)
Předkládaná diplomová práce pojednává o organických pigmentech diketopyrrolopyrrolech (DPPs), které disponují vlastnostmi uplatnitelnými v atraktivních a perspektivních oblastech organické elektroniky a fotoniky. Provedena byla modifikace jejich skeletu prostřednictvím nukleofilní substituce alkylovými řetězci, kdy bylo připraveno 5 sérií derivátů. Studována byla regioselektivita N-alkylace a také fotofyzikální vlastnosti připravených derivátů. Klíčovým produktem této práce je N,N'-ethyladamantylový derivát DPP, který vykazoval ambipolární charakteristiky s excelentní hodnotou mobilit elektronů 0,2 cm2 V–1 s–1. Dále byla u zmíněného derivátu prodloužena -konjugace o 1, resp. 2 thiofenové jednotky v pozicích 3,6 a zkoumán byl vliv této modifikace na optické vlastnosti výsledných derivátů. Připraven byl také nový modifikovaný N,N'-nesubstituovaný derivát DPP a studována byla rovněž inkorporace formylových funkčních skupin do klíčového N,N'-ethyladamantylového derivátu DPP.
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Nature-inspired macro cyclic systems for bioorganic applications
Prekopová, Terézia ; Cigánek, Martin (oponent) ; Krajčovič, Jozef (vedoucí práce)
The bachelor thesis deals with nature-inspired macrocyclic compounds and their possible use in organic bioelectronics. The theoretical part of this bachelor thesis introduces semiconductor materials in organic bioelectronics and provides a general overview of selected classes of macrocyclic compounds currently occurring. It includes their history, properties, reactivity and use in various industries. An important point of this part are cyclodextrins, which are characterized by their high biocompatibility and affinity for a wide range of guests depending on the structure of the cyclodextrin. They are capable of molecular recognition to form inclusion complexes with guest particles. The work also deals with chemical modifications of cyclodextrins in order to improve selected physicochemical properties and practical applications of cyclodextrins. The experimental part consists of the synthesis, purification and characterization of key macrocyclic -cyclodextrin derivatives selectively modified at position 6 of one glucopyranose unit for the synthesis and study of advanced supramolecular structures for potential applications in organic bioelectronics.
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Studium dielektrických vlastností struktur tenkých vrstev organických materiálů
Pospíšil, Jan ; Boušek, Jaroslav (oponent) ; Mikula, Milan (oponent) ; Zmeškal, Oldřich (vedoucí práce)
Dizertační práce je zaměřena na studium elektrických a zejména dielektrických vlastností tenkých vrstev organických materiálů, které mohou nacházet své uplatnění v organické elektronice a dalších odvětvích. Teoretická část se věnuje využití organických materiálů v organických fotovoltaických článcích, způsobům jejich depozice a metodám charakterizace. Jsou zde dále popsány teoretické poznatky o dielektrické spektroskopii včetně metod stanovení fyzikálních vlastností a vyhodnocení experimentálních dat. Experimentální část se věnuje studiu nízkomolekulárních organických solárních článků s objemovým heteropřechodem složeného z elektron donorní molekuly DPP(TBFu)2 a elektron akceptorních derivátů fullerenu PC60BM, PC70BM a TC60BM. Experimentální část je rozdělena na dvě hlavní části. První část se věnuje studiu dějů probíhajících na rozhraní aktivní vrstva/kontakt, druhá část se potom zaměřuje zejména na transportní procesy uvnitř struktury fotovoltaických článků a obsahuje i studium perovskitových solárních článků.
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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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