Załącznik nr 2 A bstract o f the doctoral dissertation titled:
„Synthesis o f selected 7i-conjugated dialkoxybenzene systenis with term inal chalcogenophene units”
A uthor: R adosław M otyka, M .Sc. Eng. Supervisor: N ikodem Kuźnik, Ph.D. Eng., D.Sc.
N um erous indications can be found in the literaturę that benzene ring system s conjugated with chalcogenophenes can be prom ising precursors o f conductive polym ers. The purpose o fth is w ork w as to synthesize such m odel com pounds incorporating different structural elem ents, including: alkoxy groups at the benzene ring, vinyl bonds o f different stereo configuration betw een the arom atic units, or electron-w ithdraw ing groups attached to the conjugated system.
The first part o f the w ork includes a com prehensive literaturę survey to select structures with the m ost prom ising optoelectronic properties. Based on this analysis, four m olecular m odels w ere designed, successively: l,4-dialkoxy-2,5-bis[2-(chalcogenophen-2-yl)ethenyl]benzenes, l,4-dialkoxy-2,5-bis[(Z )-l-cyano-2-(chalcogenophen-2-yl)ethenyl]benzenes, l,4-dialkoxy-2,5- bis[(£)-2-cyano-2-(chalcogenophen-2-yl)ethenyl]benzenes and 1,4-dialkoxy-2,5-bis(chalcogenophen-2-yl)benzenes, for which efficient synthesis pathw ays were prospected and developed using the retrosynthetic approach.
The second part o f the w ork describes the synthesis o f above-m entioned system s and detailed spectroscopic characterization o f the obtained com pounds. 16 classes o f com pounds were obtained in total according to synthetic pathw ays as short as 3 stages, with the longest ones involving 6 steps. The starting m aterials for all targets w ere hydroąuinone and 4-hydroxybenzaldehyde, w hich w ere converted into sym m etric and asym m etric hydroquinone ethers. Those ethers w ere subseąuently halogenated or halogenom ethylated. The halogenom ethyl derivatives w ere further transform ed into cyanom ethyl com pounds, diethylphosphonates, phosphonium salts and terephthaldehydes. Finał products w ith vinyl bonds in their structure w ere synthesized by the condensation reactions (W ittig, H orner-W adsw orth- Em m ons or K noevenagel), w hereas for the synthesis o f com pounds w ithout this bond, the coupling reactions (Suzuki-M iyaura and Stille) w ere used instead. Several products obtained as a m ixture o f isom ers in the W ittig reaction were separated into individual com ponents using high-perform ance liquid chrom atography (HPLC).
