ZIOC scientists obtained a new building block for the synthesis of components of organic solar cells and LEDs
Organic photovoltaics is an emerging field of technology that makes it possible to use small amounts of inexpensive, non-toxic materials for energy production and to easily change the characteristics of the materials used. The chromophores applied consist of combinations of electron-donating and electron-withdrawing groups linked either directly or through π-conjugated bridges. Electron-deficient π-conjugated building blocks play an essential role in achieving the most important characteristics of dyes, such as light absorption, light emission and charge carrier mobility in materials by reducing the band gap due to intramolecular charge transfer. Their choice is critical to achieving high performance in bulk heterojunction solar cells, dye-sensitized solar cells, n-type organic field-effect transistors, near-infrared absorbing and emitting materials, and electrochromic materials.
Researchers of the Laboratory of Polysulfur-Nitrogen Heterocycles of the Zelinsky Institute developed an effective method for the preparation of hydrolytically and thermally stable 4,8-dibromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole), a new building block, the structure of which was proved by X-ray diffraction analysis. Optimum conditions were found for selective aromatic nucleophilic substitution of both one and two bromine atoms under the action of various N,S-nucleophiles. In addition, the behavior of the obtained dibromide in cross-coupling reactions was studied and various mono- and diaryl(hetaryl) derivatives were synthesized, which can be considered as useful compounds for the synthesis of components of organic solar cells and LEDs.
Timofey N. Chmovzh, Daria A. Alekhina, Timofey A. Kudryashev, Oleg A. Rakitin Efficient synthesis of 4,8-dibromo derivative of strong electron-accepting benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) and its SNAr and cross-coupling reactions // Molecules, 2022, 27, 7372. DOI: 10.3390/molecules27217372.