Highly electrochemically and thermally stable donor-π-acceptor triphenylamine-based hole-transporting homopolymers oxidative polymerization

• Published in: New journal of chemistry Vol. 46; no. 25; pp. 12311 - 12317
• Main Authors: Luponosov, Yuriy N, Solodukhin, Alexander N, Chuyko, Irina A, Peregudova, Svetlana M, Ponomarenko, Sergey A
• Format: Journal Article
• Published: 27.06.2022
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d2nj01758j

Development of organic semiconducting polymers combining simple and scalable synthesis with high stability, solubility and hole mobility is in high demand. In this work, we report two novel D-π-A triphenylamine-based homopolymers having thiophene as a side π-spacer linked to either hexyl- or 4-fluorophenyldicyanovinyl electron-withdrawing groups. The homopolymers can be easily synthesized via oxidative polymerization at room temperature of the corresponding monomers in the presence of FeCl 3 as an oxidant. The polymers possess a number of valuable properties for application in organic and hybrid optoelectronics, among which are high electrochemical and thermal stability ( T d is up to 594 °C; coke yield up to 90%), good solubility (up to 90 g L −1 in chloroform), high glass transition temperature (up to 223 °C), efficient light absorption in the UV-Vis region, low-lying HOMO energy levels ( ca. 5.36 eV) and sufficient hole mobility (up to 7 × 10 −5 cm 2 V −1 s −1 ) without any posttreatment in thin films. Polymers combining high electrochemical and thermal stability, good solubility, high T g and high coke residue with low-lying HOMO levels and reasonable hole mobilities in thin films are reported in this study.