Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics

• Published in: Monatshefte für Chemie Vol. 154; no. 5; pp. 543 - 551
• Main Authors: Sigl, Marco, Rath, Thomas, Schlemmer, Bettina, Fürk, Peter, Trimmel, Gregor
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.05.2023; Springer Nature; Springer Nature B.V
• Subjects: Analytical Chemistry; Chemical reactions; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Copolymerization; Copolymers; Inorganic Chemistry; Optimization; Organic Chemistry; Organic light emitting diodes; Original Paper; Photoluminescence; Photovoltaic cells; Physical Chemistry; Physical Sciences; Polymers; Quinoxalines; Science & Technology; Solar cells; Theoretical and Computational Chemistry; Fluorescence; Density functional theory; OLED; Absorption spectra; Polycondensation; Polymerizations; POLYMERS; DESIGN; DEVICES
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-022-03030-7

Quinoxaline has recently gained interest as monomer in conjugated copolymers because of its easy synthetic accessibility and successful use in highly efficient organic solar cells. In this contribution, we introduce a quinoxaline–fluorene-co-polymer, PFQ10, synthesized by copolymerization of 5,8-dibromo-6,7-difluoro-2-[(2-hexyldecyl)oxy]quinoxaline and 9,9-dioctyl-9 H -9-fluorene-2,7-bis(boronic acid pinacol ester) using the Suzuki–Miyaura reaction. By optimization of the reaction conditions, polymers with molecular weights up to 17.2 kDa and a low dispersity of 1.3 were obtained. PFQ10 showed blue photoluminescence with an emission maximum at 459 nm and a relative fluorescence quantum yield of 0.37. As proof of principle, PFQ10 was employed in organic light-emitting diodes and showed a blue–green electroluminescence. Graphical abstract