Issue 16, 2023

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

Abstract

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 sp2-N in the aromatic ring. Theoretical calculation results showed that MeBTzO has higher reactivity than its non-oxide sp2-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 μe of 0.11 cm2 V−1 s−1 compared to PDPPMeBT with a μe of 7.49 × 10−3 cm2 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
24 feb 2023
Accepted
22 mar 2023
First published
22 mar 2023

Polym. Chem., 2023,14, 1945-1953

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

X. He, F. Ye, J. Guo, W. Chang, B. Ma, R. Ding, S. Wang, Y. Liang, D. Hu, Z. Guo and Y. Ma, Polym. Chem., 2023, 14, 1945 DOI: 10.1039/D3PY00207A

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