Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxidative coupling polymerization. Polymerization in tetrahydrofuran using a Cu-amine complex oxidant under O2 atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol−1. The structure of the polymer was characterized by 1H and 13C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer ortho position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 °C that corresponded to 5% weight loss. The UV–vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic devices.
Bibliographical noteFunding Information:
This work was supported by Korea Institute of Energy Technology Evaluation and Planning (KETEP) Grant funded by the Korea government (MOTIE) (20191510301070, Development dissolved boron removal system contained in effluent of discharged from liquid radioactive waste treatment system).
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- Oxidative coupling polymerization
- Regiocontrolled polymer