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Chiral Carbon-rich Materials – From Single Molecule to Functional Layers.
Žádný, Jaroslav ; Storch, Jan ; Strašák, Tomáš ; Krbal, M. ; Hrbáč, J. ; Vacek, J.
Comprehensive study of two different carbon-rich materials properties – [6]helicene and 1-butyl-3-(2-methyl[6]helicenyl)imidazolium bromide – and their thin films is presented. Because of different solubility, diverse preparation approaches had to be employed – electropolymerization and spin-coating. Spectroscopic and electrochemical properties were investigated along with examples of their practical use as detectors of biomolecules (e.g. DNAs). A high application potential of helicene-based carbon-rich materials in development of new optoelectronic devices is demonstrated.
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Potential-driven On/Off Switch Strategy for the Electrosynthesis of [7]Helicene-derived Polymers.
Žádný, Jaroslav ; Storch, Jan ; Strašák, Tomáš ; Církva, Vladimír ; Hrbáč, J. ; Fekete, Ladislav ; Pokorný, Jan ; Bulíř, Jiří ; Vacek, J.
3-([7]H elicen-9-yl)-thiophene hybrid monomer was electrooxidized in acetonitrile by cyclic voltammetry with anodic potential limits of +1.5 V or +2.5 V, resulting in a conductive and non-conductive polymer, respectively. The electrochemical findings were supplemented by microscopy investigations; UV-Vis, fluorescence and vibrational spectroscopies, ellipsometry measurements and computational chemistry. The electrodeposited polymers could be used for the further development of materials applicable in organic electronics and sensing technologies.
Plný tet: SKMBT_C22017111612582 - PDF
Plný text: content.csg - PDF
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A Short Overview of the Electrochemistry of Helical Polyaromatics.
Vacek, J. ; Hrbáč, J. ; Zatlouklová, M. ; Storch, Jan
Here we describe the electrochemical behavior of a group of polyaromatics designated helicenes. These compounds are finding many applications in optoelectronics, catalysis and chiral separation. Thus it is important to investigate the electrochemical and optical behavior of helicenes with respect to improving their application potential and our knowledge of strategies for their surfaces immobilization. Electrochemical analyses were performed in acetonitrile and in aqueous media with glassy carbon and indium tin oxide electrodes. Specifically, [n]helicenes and their salts 1-buty1-3-(2-methy1[6]heliceny)-immidazolium bromide and 3-([7]helicene-9-y1)thiophene were investigated, the application of acquired electrochemical data is disussed, especially in terms of optoelectronics and the construction of semi-conductive devices.
Plný tet: Jetrichovice 2016 - PDF
Plný text: content.csg - PDF
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Exploration of 9-Bromo[7]helicene Reactivity
Žádný, Jaroslav ; Jakubec, Martin ; Velíšek, Petr ; Sýkora, Jan ; Storch, Jan
Our new microwave assisted photodehydrocyclisation and completely reviewed synthetic approach for a multi-gram scale production of 9-bromo-[7]helicene led us to explore the reactivity of this compound mainly in Pd-catalysed reactions and to the further functionalization of this molecule. Next to other transformations, palladium catalysed carbon – heteroatom coupling reactions provide a large portfolio of racemic helicenes bearing different functional groups in good to excellent yields. Many of the reactions are performed in the microwave initiator saving reaction time to a minimum comparing with conventional and known synthetic methods. Such prepared compounds can undergo further synthetic reactions or can be used on a field of molecular electronics, surface chemistry or in other applications. The separation of racemic mixtures is under running in our lab. Optically pure compounds of such a type can open new possibilities in their use.
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