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In recent years, the direction of organic photovoltaics has been actively developing, and new materials for organic solar cells (OSCs) are elaborated. Advances in this area are associated with the development of new non-fullerene acceptor (NFA) materials, so an important task for researchers is the development of new complementary donor materials. Organic small molecules D-π-A are conjugated linear or star-shaped structures, and are of great importance as donor material for OSCs. Devices based on them show high efficiency, so the development of new approaches to the molecular design and synthesis of these molecules is of particular interest. Moreover, a thorough understanding of the structure-property correlations of new generations of acceptor and donor materials is of great importance for further progress in the field of OSCs. Here we report on the series of oligomers, based on a conjugated benzotriindole or benzodiindole moiety, conjugated through bithiophene π-spacer with N-hexylrhodanine, 2-ethylhexylcyanoacetate or hexyldicyanovinyl terminal electron-withdrawing groups. All precursors and the target compounds were characterized by 1H and 13C NMR spectroscopy and size exclusion chromatography in an individual state. Optical, thermal and electrochemical properties of molecules were studied and compared. The molecules were tested as donor materials with ITIC and Y6 as the acceptor in organic solar cells.