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Photochemical Synthesis of Aza-aromatic Compounds.
Kos, Martin ; Žádný, Jaroslav ; Storch, Jan ; Sýkora, Jan ; Církva, Vladimír
Herein we report synthesis of series of novel both aza- and diaza-helicenes, and phenacenes, which were prepared mainly by photocyclization of corresponding imine precursors. Reaction conditions of photocyclization (i.e. solvent, photocatalyst, type of irradiation, use of water scavenger) were optimized and enhanced. Usage of TEMPO as oxidizing agent leads to improvement of yields up to 72 %. Prepared 2-pyridyl substituted azaphenacenes will be utilized for preparation of potential semiconductive layers in cooperation with IMC of the CAS.
Plný tet: SKMBT_C22017111612580 -  PDF
Plný text: content.csg - PDF
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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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Preparation of Partially Fluorinated Polyaromatics by Photocyclization of Stilbenes.
Jakubík, Pavel ; Storch, Jan ; Žádný, Jaroslav ; Pfleger, Jiří ; Církva, Vladimír
Synthetic strategies to partially fluorinated polyaromatics by photocyclization were examined, leading to both 1,2,3,4-tetrafluoro[6]helicene (1) and 1,2,3,4,13,14,15,16-octafluoro[6]helicene (2), and to 1,2,3,4-tetrafluoro[5]phenacene (3) and 1,2,3,4-tetrafluoro[6]phenacene (4). Thin films of the prepared compounds were characterized for their electrical properties and incorporated into OFET structures.
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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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Ruthenium (II) Complexes with 6,7-Diaza[5]phenacene.
Beránek, Tomáš ; Žádný, Jaroslav ; Jakubík, Pavel ; Církva, Vladimír ; Storch, Jan
In this work we focused on preparation of novel bidentate and fully aromatic N,N-ligand and its ruthenium complexes. 6,7-Diaza[5]phenacene (1) was synthetized from 4-bromoisoquinoline by microwave-assisted tandem Hyama-Heck cross coupling reaction3 followed by photocyclization (Scheme 1). With 6,7-diaza[5]phenacene (1) in our hand, we prepared some new ruthenium(II) complexes (e.g. 2) , characterized them from structural point of view and determined some of their electronic and optical properties with regard to their application potential.
Plný tet: SKMBT_22316112114160 - PDF
Plný text: content.csg - PDF
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