An N -oxide containing conjugated semiconducting polymer with enhanced electron mobility via direct (hetero)arylation polymerization
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...
Saved in:
Published in | Polymer chemistry Vol. 14; no. 16; pp. 1945 - 1953 |
---|---|
Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Cambridge
Royal Society of Chemistry
25.04.2023
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | 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. |
---|---|
ISSN: | 1759-9954 1759-9962 |
DOI: | 10.1039/D3PY00207A |