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Organic semiconductor materials are actively developed and researched, which opens up broad prospects for the development of modern scientific and technological areas. Before synthesizing new compounds, it is extremely important to carefully design their structure, since it determines not only the conductive and electrochemical properties, but also the phase behavior, solubility and ability to certain types of crystal packing, which ultimately affects the electrical characteristics and the possibility of creating functional devices. Of particular interest are structures combining electron-donor (D) and electron-acceptor (A) fragments (D-A). Such systems allow, by varying the strength and nature of the donor and acceptor components, to control molecular energy levels in a wide range, achieving the desired properties in target compounds. Organic molecules built on the basis of condensed heteroaromatic fragments are of particular interest, since their rigid structure provides effective π-conjugation, high conductivity, oxidation stability and dense molecular packing. In the work a number of semiconductor oligomers of D-A structure are synthesized, which are based on donor heteroaromatic fragments: known benzothieno[3,2-b]benzothiophene and indole[3,2-b]indole. Keto- and dicyanovinyl fragments are used as acceptor groups, and the role of conjugated π-spacers linking D and A parts of the molecules is performed by benzene links. The schemes of synthesis of new semiconductor oligomers and the results of studies of their physicochemical properties will be shown: electrochemical, optical and thermal, phase behavior, analysis of the crystal structure including thermal PCA. Based on the presented data, the relationships between the structure and final properties of the obtained substances will be revealed, what effect the components and their replacement have on the physicochemical properties, a comparison of two donor blocks with each other, an assessment of the effect of sulfur and nitrogen heteroatoms. The identified relationships will allow us to draw conclusions about how to control and achieve the desired properties of organic semiconductors of this type. An assessment of the possibilities and prospects for using the obtained materials in organic electronics applications was also made.
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