One-pot homopolymerization of thiophene-fused isoindigo for ambient-stable ambipolar organic field-effect transistors

Abstract

The homopolymer that was directly obtained via one-pot polymerization exhibited much higher ambipolar transport behavior than the copolymer.

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

“…[62] For isoindigo-derived homopolymers, they were synthesized by Stille and Suzuki cross-couplings of dibrominated and distannylated/diborylated isoindigo derivatives or dibrominated isoindigo derivatives and hexamethylditin/bis(pinacolato)diboron (Figure 2c). [60,[63][64][65] In particular, Mei' group successfully prepared asymmetric isoindigo-derived homopolymer by DArP. In this report, the polymerization precursor was functionalized by both CBr bond and CH bond.…”

“…[66] Wan and co-workers synthesized homopolymer P108 of M21 using one-pot polymerization method. [63] The weak steric hindrance between the adjacent units contributed to good polymer planarity and crystallinity. The high molecular weight facilitated the formation of interconnected polymer networks.…”

Recent advances in the application of isoindigo derivatives in materials chemistry

“…Thus, the dihedral angle 179° in a furan polymer determines the conductivity μ h /μ e = 0.01 cm 2 ⋅V −1 ⋅s −1 /1.6⋅10 −3 cm 2 ⋅V −1 ⋅s −1 , while polymers containing thiophene or p-phenylene spacers did not possess conductivity at all due to the lower planarity (dihedral angle 143°, Scheme 26, Table 7). Homopolymers based on isoindigo of various types have also been used in the design of transistors [97][98][99][100]. In order to reduce the influence of factors of conformational and energy disordering inherent in all isoindigo polymers in which aromatic fragments are linked by a single bond, a number of homopolymers 53 was obtained by the aldol polycondensation reaction [97].…”

Ambipolar polymers for transistor applications

“…(e), (f) Characteristics of PTII‐2 annealed at 200 °C and tested under ambient conditions. (Adapted from reference 34 ; Copyright 2017, RSC Publishers. )…”

“…A new method termed one‐pot polymerization to synthesize homopolymers of thiophene‐fused isoindigo (TII) for ambipolar OFETs either via Suzuki condensation polymerization (PTII‐1) or Stille condensation polymerization (PTII‐2) was proposed by Zhang and coworkers 34 . In comparison, P(TIIco‐II), which was synthesized by TII copolymerizing with II, was obtained to further illustrate the relationship between structure and properties; this PTII‐2 based OFET exhibited ambipolar transport behavior with balanced hole and electron mobilities of 0.065 and 0.15 cm 2 V −1 s −1 respectively after annealing (as illustrated in Figs 5(e) and 5(f)), two orders higher than those of P(TII‐co‐II).…”