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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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Bio-inspired uracil building blocks as terminal functional groups for electronic materials
Krusberský, Vojtěch ; Ivanová, Lucia (referee) ; Richtár, Jan (advisor)
This bachelor thesis focuses on synthesis, purification and characterization of bio-inspired electron-accepting motifs based on N,N’-dialkylated barbituric acid derivatives for potential applications in the field of N-type organic semiconductors. The theoretical part deals with organic semiconductors and principles of their conductivity. Further covered topics are uracil, barbituric acid and its derivatives, synthetic approaches to target molecules and their analogues are also included. Within the experimental part two types of alkyl substituents were chosen – a flexible butyl and a bulky and rigid adamantylethyl. Both were incorporated into the structure via appropriate dialkylurea, which underwent condensation in the next phase. The final step of the synthetic route was the Knoevenagel condensation with a -conjugated trimer.
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Synthesis of soluble nature-inspired N, N-alkylated riboflavin derivatives, study of the effect of alkyl groups
Ivanová, Lucia ; Maier,, Lukáš (referee) ; Krajčovič, Jozef (advisor)
By flavin's unique structure, nature predestined riboflavin and its derivatives to the participation in redox processes within the bodies of all the living organisms. These biomolecules draw attention with intriguing optical properties and photosensitising abilities. Nature-inspired flavin derivatives share these qualities, and there is also a possibility of fine-tuning for the particular application from the chemical point of view. The thesis deals with two main aims. The first aim handles the synthesis of the trimer heteroaromatic precursor and 1,2-diketone. These key intermediates are essential for the future synthesis of the central aromatic core of the novel NH-free non-fused flavin derivative. The thesis introduces and verifies three approaches, including oxidation of diarylalkynes, nucleophilic addition of a corresponding organolithium compound to a Weinreb amide and benzoin condensation. The second aim covers the properties customization of NH-free fused systems by implementation of linear and bulky alkyl side-chains on the nitrogen atoms N1 and N3 of the alloxazine dilactam. N,N-alkylation introduced an increase in solubility in common organic solvents dichloromethane and chloroform. For the derivatives with 2-(adamantan-1-yl)ethyl substituents, high thermal stability was observed via TGA.
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Utilisation of the double bond in the synthesis of new types of molecular photoswitches applicable in biological systems
Bartošová, Aneta ; Ivanová, Lucia (referee) ; Cigánek, Martin (advisor)
This bachelor thesis deals with the synthesis and characterization of new advanced organic molecules with the utilization of the structure motive of the double bond for purposes of application as molecular photoswitches. The theoretical part of the thesis introduces the types of molecules, their characterization and the comparison of fundamental isomers. In the next, section, the mechanisms of isomerization are presented, synthesis via cross-coupling reaction, comparison of advantages and disadvantages of methods and possible application of these molecules in medicine, biological systems and in material chemistry. In the experimental part of the thesis, the multistep synthesis of two final derivatives with an imine bond is described, which can possibly secure the application of these original materials like molecular photoswitches.
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Bio-inspired uracil building blocks as terminal functional groups for electronic materials
Krusberský, Vojtěch ; Ivanová, Lucia (referee) ; Richtár, Jan (advisor)
This bachelor thesis focuses on synthesis, purification and characterization of bio-inspired electron-accepting motifs based on N,N’-dialkylated barbituric acid derivatives for potential applications in the field of N-type organic semiconductors. The theoretical part deals with organic semiconductors and principles of their conductivity. Further covered topics are uracil, barbituric acid and its derivatives, synthetic approaches to target molecules and their analogues are also included. Within the experimental part two types of alkyl substituents were chosen – a flexible butyl and a bulky and rigid adamantylethyl. Both were incorporated into the structure via appropriate dialkylurea, which underwent condensation in the next phase. The final step of the synthetic route was the Knoevenagel condensation with a -conjugated trimer.
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Synthesis of soluble nature-inspired N, N-alkylated riboflavin derivatives, study of the effect of alkyl groups
Ivanová, Lucia ; Maier,, Lukáš (referee) ; Krajčovič, Jozef (advisor)
By flavin's unique structure, nature predestined riboflavin and its derivatives to the participation in redox processes within the bodies of all the living organisms. These biomolecules draw attention with intriguing optical properties and photosensitising abilities. Nature-inspired flavin derivatives share these qualities, and there is also a possibility of fine-tuning for the particular application from the chemical point of view. The thesis deals with two main aims. The first aim handles the synthesis of the trimer heteroaromatic precursor and 1,2-diketone. These key intermediates are essential for the future synthesis of the central aromatic core of the novel NH-free non-fused flavin derivative. The thesis introduces and verifies three approaches, including oxidation of diarylalkynes, nucleophilic addition of a corresponding organolithium compound to a Weinreb amide and benzoin condensation. The second aim covers the properties customization of NH-free fused systems by implementation of linear and bulky alkyl side-chains on the nitrogen atoms N1 and N3 of the alloxazine dilactam. N,N-alkylation introduced an increase in solubility in common organic solvents dichloromethane and chloroform. For the derivatives with 2-(adamantan-1-yl)ethyl substituents, high thermal stability was observed via TGA.
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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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