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The synthesis of functionalised electron donors and acceptors and the study of their interaction
Rejchrtová, Blanka ; Starý, Ivo (advisor) ; Betík, Robert (referee)
This work is focused on the stepwise preparation of model dimer, containing tetrathiafulvalene as electron donor unit. Main method used in the synthesis was Sonogashira coupling. Theoretical part deals with current state of research in the field of nanoscience and nanotechnology and molecular electronics. It is focused on noncovalent interactions, especially of the electron donor - electron acceptor (CT complexes). Properties of tetrathiafulvalene and its derivatives are described in detail as well as mechanism of Sonogashira coupling. In the part devoted to the results and discussion is described preparation of monomeric precursor from known TTF alcohol and new iodobenzylbromide with protected acetylene function. Stepwise synthesis utilizing Sonogashira coupling leads to the preparation of model dimer in moderate yield. All new compounds were characterized by spectral methods (NMR, MS, FTIR) and by elemental analysis, eventually HR-MS.
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The D-A and pi-pi interactions and their use in self-assembly
Rejchrtová, Blanka ; Starý, Ivo (advisor) ; Kotora, Martin (referee)
The D-A and π-π Interactions and Their Use in Self-Assembly Due to their well-defined shape, size and properties gold nanoparticles represent an advantageous platform for the study of non-covalent interactions between ligands anchored to their surface both in solution and in monolayers or thin films. The aim of this thesis was the synthesis of ligands for gold nanoparticles bearing an anchoring group at one end and a planar π-electron rich pyrene unit at the other. Six structurally variable ligands were prepared differing in the pyrene substitution pattern and the spacer between the aromatic part and the acetylated thiol function. Furthermore, a synthetic pathway leading to extended π-electron systems (both electron rich and electron poor) such as hexabenzocoronene derivatives and its fragments was explored. The key steps in the synthesis of these compounds are the cyclization reactions of alkynes leading to polycyclic intermediates and their ensuing cyclodehydrogenation (Scholl reaction). All of the prepared ligands and their intermediates were characterized by spectroscopic methods. The structure of the key hexakis(pentafluorosulfanyl-phenyl)benzene was confirmed by single crystal X-ray crystallography. The prepared ligands bearing a pyrene unit were deacetylated and anchored to the surface of...
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The D-A and pi-pi interactions and their use in self-assembly
Rejchrtová, Blanka ; Starý, Ivo (advisor) ; Kotora, Martin (referee)
The D-A and π-π Interactions and Their Use in Self-Assembly Due to their well-defined shape, size and properties gold nanoparticles represent an advantageous platform for the study of non-covalent interactions between ligands anchored to their surface both in solution and in monolayers or thin films. The aim of this thesis was the synthesis of ligands for gold nanoparticles bearing an anchoring group at one end and a planar π-electron rich pyrene unit at the other. Six structurally variable ligands were prepared differing in the pyrene substitution pattern and the spacer between the aromatic part and the acetylated thiol function. Furthermore, a synthetic pathway leading to extended π-electron systems (both electron rich and electron poor) such as hexabenzocoronene derivatives and its fragments was explored. The key steps in the synthesis of these compounds are the cyclization reactions of alkynes leading to polycyclic intermediates and their ensuing cyclodehydrogenation (Scholl reaction). All of the prepared ligands and their intermediates were characterized by spectroscopic methods. The structure of the key hexakis(pentafluorosulfanyl-phenyl)benzene was confirmed by single crystal X-ray crystallography. The prepared ligands bearing a pyrene unit were deacetylated and anchored to the surface of...
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The synthesis of functionalised electron donors and acceptors and the study of their interaction
Rejchrtová, Blanka ; Betík, Robert (referee) ; Starý, Ivo (advisor)
This work is focused on the stepwise preparation of model dimer, containing tetrathiafulvalene as electron donor unit. Main method used in the synthesis was Sonogashira coupling. Theoretical part deals with current state of research in the field of nanoscience and nanotechnology and molecular electronics. It is focused on noncovalent interactions, especially of the electron donor - electron acceptor (CT complexes). Properties of tetrathiafulvalene and its derivatives are described in detail as well as mechanism of Sonogashira coupling. In the part devoted to the results and discussion is described preparation of monomeric precursor from known TTF alcohol and new iodobenzylbromide with protected acetylene function. Stepwise synthesis utilizing Sonogashira coupling leads to the preparation of model dimer in moderate yield. All new compounds were characterized by spectral methods (NMR, MS, FTIR) and by elemental analysis, eventually HR-MS.
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