| Abstract [eng] |
Organic compounds possessing optical, photoelectric or magnetic properties are used in many modern technologies. They are used in organic light-emitting diodes (OLED), optical switches and sensors, information collection and storage devices as emitters and photosemiconductors. Many different natural compounds contain bicyclic motive in their frameworks. Due to significance of this scaffold tremendous progress has been achieved in this field during the past 50 years. This scaffold allows to juxtapose two aromatic rings into close range. Physical and chemical properties of this type of compounds have been obtained and studied. Also the bicyclic motive showed the ability to transfer electron between π-systems. In addition, some works were carried out in the design of molecular receptors. The main aim of present investigation was to synthesize various non-planar bicyclic compounds containing aromatic heterocyclic fragments with nitrogen atoms and investigate their photophysical properties. The synthetic procedures of 2-aminobenzo[h]quinoline-3-carbaldehyde, 2-amino(nafto[2,3-h]quinoline)-3-carbaldehyde, 2-amino(nafto[2,3-f]quinoline)-3-carbaldehyde were optimized. A fast synthetic method was used for preparation of α,β-unsaturated bicyclic ketones in small amounts. It was shown that nitro aldehydes in these reactions deflagrated. Investigation of the interaction between bicyclic α,β-unsaturated carbonyl compounds and phenylhydrazine showed that in this type of reactions, piperidine was the best catalyst for the formation of the pyrazole ring. The optimum Friedleander condensation reaction conditions between bicyclic and heterocyclic components were strong bases (sodium hydroxide, sodium methoxide or tert-butoxide) in boiling methanol, ethanol or 1,4-dioxane. 1,10-phenanthroline moiety containing compounds were stable in acidic, neutral and alkaline media, while the 1,8-naphthyridine moiety containing compounds decomposed in acidic conditions. Interaction between bicyclic diketones and 8-aminoquinoline-7-carbaldehyde gave di-1,10-phenanthroline derivatives. Mono-1,8-naphthyridine derivatives were obtained by fusing cis-bicyclo[3.3.0]octane-3,7-dione and 2-aminoquinoline-3-carbaldehyde. Solubility of synthesized compounds was found to be low in various solvents (toluene, chloroform, 2-propanol, THF). So only thermal vacuum evaporation method is effective to prepare the layers. During investigation of the layers obtained by this method, it was observed that the material of the amorphous state slowly crystallized and the crystals formed in the layer prevented the identification and reliability of obtained results. According to the HOMO values, derived compounds could be assigned to p-type semiconductors. Benzo[h]tetrazole[1,5-a]quinoline-3-carbaldehyde and 2-aminobenzo[h]quinoline-3-carbaldehyde displayed white electroluminescence. |
