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

作者：He, Xiandong; Ye, Feng; Guo, Jia-Cheng; Chang, Wenju; Ma, Bingxu; Ding, Riqing; Wang, Sijing; Liang, Yong; Hu, Dehua^*; Guo, Zi-Hao^*; Ma, Yuguang

来源：Polymer Chemistry, 2023, 14(16): 1945-1953.

DOI：10.1039/d3py00207a

• FIELD-EFFECT TRANSISTORS
• STRUCTURE-PROPERTY CORRELATIONS
• DIRECT ARYLATION
• SOLAR-CELLS
• PERFORMANCE
• AMBIPOLAR
• DONOR
• BITHIAZOLE
• POLYCONDENSATION
• COPOLYMERS

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 mu(e) of 0.11 cm(2) V-1 s(-1) compared to PDPPMeBT with a mu(e) of 7.49 x 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.

• 单位
  广东工业大学; 南京大学