Benzodipyrrole-2,6-dione-3,7-diylidenedimalononitrile Derivatives for Air-Stable <i>n</i>-Type Organic Field-Effect Transistors: Critical Role of <i>N</i>-Alkyl Substituent on Device Performance

Dhondge, Attrimuni P.; Huang, Yixiang; Lin, Tzu Chen; Hsu, Yu-Hung; Tseng, Shin-Lun; Chang, Yu‐Chang; Chen, Henry J. H.; Kuo, Ming‐Yu

doi:10.1021/acs.joc.9b02207

Cited by 12 publications

(5 citation statements)

References 33 publications

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“…125 The Larock indole synthesis also goes through the formation of an aryl alkyne intermediate. 126 Besides, alkyne-functionalized 3,4,9,10-perylenedicarboximide (PDI) can also go through thienannulation to obtain a thiophene extended product. 127 Moreover, there are other transformations based on aryl alkynes, such as the alumina-mediated π-activation of alkynes developed by Akhmetov and co-workers very recently.…”

Section: New Synthetic Methodologies Towards N-type and Ambipolar Mat...mentioning

confidence: 99%

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

et al. 2023

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Section: New Synthetic Methodologies Towards N-type and Ambipolar Mat...mentioning

confidence: 99%

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

et al. 2023

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“…The uniform shape and tunable optical properties of the organic micro/nanocrystals, and their capability to be integrated on a large scale to a flexible substrate are extremely important for their application in OSSLs [25], LEDs [56,57], field-effect transistors [58], solar cells [59], and so on. The desirable optoelectronic performances mainly lie on the structure of the molecules and the intermolecular interactions such as the molecular arrangement mode or packing in the condensed states.…”

Section: Morphology Modulationmentioning

confidence: 99%

Advances in organic micro/nanocrystals with tunable physicochemical properties

Chen

et al. 2021

Sci. China Mater.

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Organic micro/nanocrystals based on small organic molecules have drawn extensive attention due to their potential application in organic field-effect transistors, electrochemical sensors, solar cells, etc. Herein, the recent advances for organic micro/nanocrystals from the perspective of molecule aggregation mode, morphology modulation, and optical property modulation are reviewed. The stacking mode and the intermolecular interaction depend on the molecular structure, which eventually determines the morphology of organic micro/nanocrystals. The morphologies of the organic micro/nanocrystals make the aggregates exhibit photon confinement or light-guiding properties as organic miniaturized optoelectronic devices. In this review, we conclude with a summary and put forward our perspective on the current challenges and the future development of morphology and optical tunable direction for the organic micro/nanocrystals.

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“…These naphthalene derivatives, I-2, displayed a broad absorption with two main absorption bands at 300-450 and 550-800 nm, assigned as the π-π* and intramolecular charge transfer (ICT) transitions, respectively. Benzodipyrrole-2,6dione-3,7-diylidenedimalononitrile, I-3, which was a structural analog to I-2 by replacing the naphthalene core with a phenyl moiety, was recently reported, and its electrochemical behavior was investigated by cyclic voltammetry (CV) [15]. The CV results showed reversible reduction−oxidation processes, and the LUMO levels were estimated to be −4.42 eV.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Photophysical Properties of Acceptor–Donor–Acceptor Di-2-(2-oxindolin-3-ylidene) Malononitrile Materials via Extended π–Conjugation: A Joint Experimental and Theoretical Study

Ren,

Habibi,

et al. 2023

Materials

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Many optoelectronic applications require organic semiconductor (OSC) materials with high electron affinity. In this work, a series of novel acceptor–donor–acceptor (A–D–A) materials with low-lying LUMO energy levels were designed and characterized. In this strategy, two acceptor dyes, bis-isatin and di-2-(2-oxindolin-3-ylidene) malononitrile, were connected by various π–bridges (benzene ring, benzo[c][1,2,5]thiadiazole, monothiophene, trithiophene). We varied the length of the π–conjugation of the central core and the linkage position of the acceptor core (4- vs. 6-position of the phenyl ring) to investigate the effect on the optical and electrochemical properties of the materials. We performed density functional theory (DFT) and time-dependent DFT (TD–DFT) studies to gain insight into the dyes’ electronic properties by determining the energy levels. Our findings demonstrate that with increasing acceptor strength and π–conjugation length of the core, the wavelength of the longest absorption maximum as well as their respective extinction coefficients are enhanced, which results in band-gap reduction either by lowering the LUMO and/or raising the HOMO energy level of the molecules. The potential practical utility of these materials as electron-transport materials for perovskite solar cells (PSCs) has been demonstrated.

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Benzodipyrrole-2,6-dione-3,7-diylidenedimalononitrile Derivatives for Air-Stable n-Type Organic Field-Effect Transistors: Critical Role of N-Alkyl Substituent on Device Performance

Cited by 12 publications

References 33 publications

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

Advances in organic micro/nanocrystals with tunable physicochemical properties

Tuning the Photophysical Properties of Acceptor–Donor–Acceptor Di-2-(2-oxindolin-3-ylidene) Malononitrile Materials via Extended π–Conjugation: A Joint Experimental and Theoretical Study

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