An N -oxide containing conjugated semiconducting polymer with enhanced electron mobility via direct (hetero)arylation polymerization

• Published in: Polymer chemistry Vol. 14; no. 16; pp. 1945 - 1953
• Main Authors: He, Xiandong, Ye, Feng, Guo, Jia-Cheng, Chang, Wenju, Ma, Bingxu, Ding, Riqing, Wang, Sijing, Liang, Yong, Hu, Dehua, Guo, Zi-Hao, Ma, Yuguang
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 25.04.2023
• Subjects: Aromatic compounds; Electron mobility; Electron transport; Field effect transistors; Molecular orbitals; Oxidation; Polymer chemistry; Polymerization; Polymers; Semiconductor devices; Synthesis; Transport properties
• ISSN: 1759-9954; 1759-9962
• DOI: 10.1039/D3PY00207A

In this paper, an N -oxide building block, 4,4′-dimethyl-[2,2′-bithiazole] 3,3′-dioxide (MeBTzO), was designed and synthesized by oxidation of sp 2 -N in the aromatic ring. Theoretical calculation results showed that MeBTzO has higher reactivity than its non-oxide sp 2 -N containing monomer MeBTz in direct (hetero)arylation polymerization (DHAP). Therefore, an N -oxide containing conjugated semiconducting polymer, PDPPMeBTzO, was successfully synthesized via DHAP of MeBTzO with thiophene-flanked diketopyrrolopyrrole (DPP). PDPPMeBTzO possesses a lower lowest unoccupied molecular orbital (LUMO) than the non-oxide analogous polymer PDPPMeBTz, which will facilitate electron injection and transport in organic field-effect transistors (OFETs). As a result, PDPPMeBTzO has obviously enhanced electron transport properties with a higher μ e of 0.11 cm 2 V −1 s −1 compared to PDPPMeBT with a μ e of 7.49 × 10 −3 cm 2 V −1 s −1 . Our strategy demonstrated that introducing the N -oxide group in conjugated polymers has great potential for high performance ambipolar and n-type CSP materials.