Pyromellitic dithioimides: thionation improves air-stability and electron mobility of N-type organic field-effect transistors

Yang, Te‐Fang; Huang, Sheng-Han; Chiu, Yi-Pang; Chen, Bo-Hsiang; Shih, Yu-Wei; Chang, Yu‐Chang; Yao, Jie-Yi; Lee, Yao-Jen; Kuo, Ming‐Yu

doi:10.1039/c5cc04674b

Cited by 18 publications

(17 citation statements)

References 38 publications

(5 reference statements)

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“…Enhancement of the electron mobility upon replacing oxygen with sulfur was found in the PyDI derivative. 180 Under ambient conditions, the thionated…”

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confidence: 99%

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

2017

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aIn recent years, organic semiconducting materials have enabled technological innovation in the field of flexible electronics. Substantial optimization and development of new p-conjugated materials has resulted in the demonstration of several practical devices, particularly in displays and photoreceptors.However, applications of organic semiconductors in bipolar junction devices, e.g. rectifiers and inverters, are limited due to an imbalance in charge transport. The performance of p-channel organic semiconducting materials exceeds that of electron transport. In addition, electron transport in p-conjugated materials exhibits poorer atmospheric stability and dispersive transient photocurrents due to extrinsic carrier trapping. Thus development of air stable n-channel conjugated materials is required. New classes of materials with delocalized n-doped states are under development, aiming at improvement of the electron transport properties of organic semiconductors. In this review, we highlight the basic tenets related to the stability of n-channel organic semiconductors, primarily focusing on the thermodynamic stability of anions and summarizing the recent progress in the development of air stable electron transporting organic semiconductors. Molecular design strategies are analysed with theoretical investigations.

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“…Enhancement of the electron mobility upon replacing oxygen with sulfur was found in the PyDI derivative. 180 Under ambient conditions, the thionated…”

mentioning

confidence: 99%

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

2017

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“…The interelectronic repulsion induced by an additional electron is higher in oxygen than that in sulfur. Therefore, the electron-withdrawing ability of the imide group is lower than expected [ 45 ]. The low lying LUMO level could improve the air-stability of the devices and on account of the intense S–S intermolecule and intramolecule interactions, the material could achieve higher charge mobility.…”

Section: Introductionmentioning

confidence: 93%

“…Previously, this functionality had been mainly studied in biological chemistry [ 41 , 42 ]. However, the introduction of thionating materials for organic electronics has been gradually introduced [ 43 , 44 , 45 , 46 ]. These thionation methods typically lead to a lowering of the LUMO level and increaed electron affinity.…”

Section: Introductionmentioning

confidence: 99%

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Novel Conjugated Polymers Prepared by Direct (Hetero) arylation: An Eco-Friendly Tool for Organic Electronics

et al. 2018

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The phthalimide (PhI) moiety has been attracting more attention as an excellent acceptor building block in donor-acceptor (D-A) conjugated polymers. In this paper; three D-A conjugated polymers with or without thiocarbonyl moieties are successfully prepared by the direct (hetero)-arylation polymerization (DHAP), which is an atom efficient and facile synthetic strategy to obtain polymer materials. Compared with the traditional carbon-carbon coupling reactions, this method possesses more advantages, including: fewer synthetic steps, avoidance of the preparation of the organometallic reagents, higher atom economy and fewer toxic byproducts, better compatibility with chemically sensitive functional groups and so on. All three of these designed PhI-based polymers exhibited favourable optoelectronic and thermal performance. The optical, thermodynamic and electrochemical properties of the synthesized polymers were systematically investigated using ultraviolet-visible (UV-vis) spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and cyclic voltammetry (CV). The results of these three polymers indicated that thionation of the carbonyl was a highly effective methods to improve the properties of PhI-based polymers; and provided impetus for the development of thionated PhI derivatives for organic electronic applications.

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“…They also show potential applications in photovoltaic devices (Kanosue et al, 2016) and organic semiconductors (Zheng et al, 2008). Not only pyromellitic diimide derivatives, but also pyromellitic diimides substituted with sulfur have potential applications in organic semiconductors (Yang et al, 2015). We have reported copper(I) coordination polymers based on pyromellitic diimide derivatives (Park et al, 2011), which showed colour change owing to intermolecular halogen-interactions.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2,6-dibenzylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrathione

Park

Kim

et al. 2017

Acta Cryst E

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Pyromellitic dithioimides: thionation improves air-stability and electron mobility of N-type organic field-effect transistors

Abstract: Thionation and fluorination of pyromellitic diimides (PyDIs) increased the electron mobility and on/off ratio of the original diimides by two orders of magnitude and improved the threshold voltage and air-stability of diimide compounds.

Cited by 18 publications

References 38 publications

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

Novel Conjugated Polymers Prepared by Direct (Hetero) arylation: An Eco-Friendly Tool for Organic Electronics

Crystal structure of 2,6-dibenzylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrathione

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