n-Type Organic Field-Effect Transistors Based on Bisthienoisatin Derivatives

Yoo, Dongho; Luo, Xuyi; Hasegawa, Tsukasa; Ashizawa, Minoru; Kawamoto, Tadashi; Masunaga, Hiroyasu; Ohta, Nobuhiro; Matsumoto, Hidetoshi; Mei, Jianguo; Mori, Takehiko

doi:10.1021/acsaelm.9b00105

Cited by 9 publications

(13 citation statements)

References 43 publications

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“…The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels are estimated by using cyclic voltammetry and ultraviolet visible (UV−vis) absorption spectroscopy. Bn-BTI and EtPh-BTI show two reversible reduction waves similar to those of the previous alkyl-BTI (Figure 1a), 23 whereas Bn-DBTII and EtPh-DBTII exhibit two reversible oxidation waves (Figure 1e). However, Bn-TIIG and EtPh-TIIG show two irreversible oxidation peaks (Figure 1c); thus the HOMO levels are estimated from the onset potentials (E onset ).…”

Section: ■ Results and Discussionmentioning

confidence: 53%

“…However, the mobilities of these two molecules decrease in comparison to the previously reported alkyl-BTIs. 23 The reason is roughness and many grain boundaries in the thin films, as confirmed by AFM (Figure S11a,b). In EtPh-BTI, a two-dimensional conduction path is constructed in the herringbone structure, but one of the conduction paths faces the direction vertical to the substrate in the thin films (Figure S13).…”

Section: Table 1 Summary Of Electrochemical and Optical Properties In...mentioning

confidence: 81%

“…This molecule has a linear planar structure and shows n-type OFET properties owing to the four electron-withdrawing carbonyl groups. 23 Also, we have prepared N-unsubstituted thienoisoindigo (TIIG; Scheme 1b) by the dimerization of thienoisatins, which has a planar molecular structure due to an intramolecular oxygen−sulfur (S•••O) interaction. 24 In addition, TIIG forms intermolecular sulfur−sulfur (S•••S) interactions and hydrogen bonds with adjacent molecules, so that this molecule shows moderate ambipolar OFET properties.…”

Section: ■ Introductionmentioning

confidence: 99%

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Bulky Phenylalkyl Substitutions to Bisthienoisatins and Thienoisoindigos

Yoo

Kohara

Ashizawa

et al. 2020

Crystal Growth & Design

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In order to investigate the effects of bulky substituents on the crystal structures and packing modes, N-benzyl (Bn) and N-2-phenylethyl (EtPh) substituents are introduced in bisthienoisatin (BTI), thienoisoindigo (TIIG), and dibenzothienoisoindigo (DBTII). These molecules maintain uniform stacking structures, though EtPh-BTI has a two-dimensional slippedherringbone structure. The benzyl groups are largely distorted from the molecular core, and thin films of Bn-TIIG and Bn-DBTII show poor quality due to the two kinds of molecular orientations. In contrast, the 2-phenylethyl-substituted molecules enable suitable molecular packing owing to the ethylene spacer and show relatively good thin-film qualities as well as much improved transistor properties. The BTI derivatives show only electron transport, but other compounds exhibit ambipolar transistor properties. In particular, EtPh-TIIG and EtPh-DBTII show maximum hole mobilities of about 0.04−0.05 cm 2 V −1 s −1 together with moderate electron mobilities.

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Section: ■ Results and Discussionmentioning

confidence: 53%

Section: Table 1 Summary Of Electrochemical and Optical Properties In...mentioning

confidence: 81%

Section: ■ Introductionmentioning

confidence: 99%

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Bulky Phenylalkyl Substitutions to Bisthienoisatins and Thienoisoindigos

Yoo

Kohara

Ashizawa

et al. 2020

Crystal Growth & Design

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“…Bisthienoisatin (BTI) was prepared by the oxidative coupling of thienoisatin using AgF as an oxidant. [ 21,22 ] In the case of Ph‐QBTI , phenylmagnesium bromide was used as a Grignard reagent to react with the β ‐carbonyl groups of BTI, and this was followed by a reduction using NaH 2 PO 2 /NaI/AcOH. [ 23 ] Th‐QBTI was synthesized following the same procedure except that 2‐thienylmagnesium bromide was used as the Grignard reagent.…”

Section: Resultsmentioning

confidence: 99%

Quinoidal bisthienoisatin based semiconductors: Synthesis, characterization, and carrier transport property

et al. 2020

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Novel quinoidal bisthienoisatin (QBTI) derivatives end‐capped with phenyl and thienyl groups were designed and synthesized. Single‐crystal X‐ray structure analysis of phenyl group flanked QBTI molecule confirmed that the quinoidal structure contributed to the high planarity of the molecular skeleton and the construction of one‐dimensional stacks. The quinoidal form of bisthienoisatin derivatives displayed ambipolar carrier transport properties with mobilities of approximately 10−4 cm2 V−1 s−1. Different flanking aromatic rings considerably affected the thin‐film microstructure and hence the charge carrier transport properties of the material. The QBTI‐based narrow energy gap polymers were theoretically designed and synthesized. Delocalized quinoidal resonance of QBTI unit along the polymer backbone is of particular importance to achieve relatively high conductive state (10−3 S cm−1). We demonstrate that QBTI cores should be promising building blocks for constructing narrow energy gap semiconducting and conductive polymers.

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“…Another challenge with electron-conducting materials is the lack of air-stable electron transport; a low energy lowest unoccupied molecular orbital (LUMO) is required to prevent unwanted reactivity with moisture and oxygen. It has been shown both theoretically and empirically that a LUMO energy of about −4.0 eV is required for stable electron transport under ambient conditions. − These challenges can be addressed in part through the development of new organic semiconductors.…”

Section: Introductionmentioning

confidence: 99%

Bisisoindigo–Benzothiadiazole Copolymers: Materials for Ambipolar and n-Channel OTFTs with Low Threshold Voltages

Bennett

Hendsbee

Ngai

et al. 2020

ACS Appl. Electron. Mater.

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The development of design strategies in both ambipolar and electron-conducting organic thin-film transistor (OTFT) materials is important for producing high-performance materials and devices in organic electronics. Isoindigo donor− acceptor polymers have been well studied as hole-conducting materials in OTFTs, while more electron-deficient, acceptor-rich isoindigo polymers have been underexplored. In this report, two common design strategies in isoindigo-based polymers, acceptor− acceptor polymers and core-expanded isoindigo structures, are combined to create copolymers of bisisoindigo, a core-expanded derivative of isoindigo, and electron-deficient benzothiadiazoles. These polymers exhibit the low energy lowest unoccupied molecular orbitals (LUMOs) required for electron transport and show ambipolar OTFT performance with hole and electron mobilities up to 4.0 × 10 −3 and 1.4 × 10 −3 cm 2 V −1 s −1 , respectively. Additionally, changing the source and drain contacts from Au to LiF/Al significantly lowered the threshold voltage due to improved alignment of the polymer and electrode energy levels. Comparisons of the optoelectronic properties between these polymers and previously reported bisisoindigo donor−acceptor polymers indicate that the increased acceptor strength lowers the frontier molecular orbital energies, while the dithienyl-benzothiadiazole unit impacts the film morphology by altering the shape of the polymer backbone.

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n-Type Organic Field-Effect Transistors Based on Bisthienoisatin Derivatives

Cited by 9 publications

References 43 publications

Bulky Phenylalkyl Substitutions to Bisthienoisatins and Thienoisoindigos

Bulky Phenylalkyl Substitutions to Bisthienoisatins and Thienoisoindigos

Quinoidal bisthienoisatin based semiconductors: Synthesis, characterization, and carrier transport property

Bisisoindigo–Benzothiadiazole Copolymers: Materials for Ambipolar and n-Channel OTFTs with Low Threshold Voltages

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