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    One-step Six-fold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors

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    Name:
    One step_one step six fold.pdf
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    1.622Mb
    Format:
    PDF
    Description:
    Accepted manuscript
    Embargo End Date:
    2021-12-14
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    Type
    Article
    Authors
    Heeney, Martin
    Kafourou, Panagiota
    Park, Byoungwook
    Luke, Joel
    Luxi, Tan
    Panidi, Julianna
    Glöcklhofer, Florian
    Kim, Jehan
    Anthopoulos, Thomas D. cc
    Kim, Ji-Seon
    Lee, Kwanghee
    Kwon, Sooncheol
    KAUST Department
    Physical Science and Engineering (PSE) Division
    Material Science and Engineering Program
    KAUST Solar Center (KSC)
    KAUST Grant Number
    CRG
    Date
    2020-12-14
    Embargo End Date
    2021-12-14
    Permanent link to this record
    http://hdl.handle.net/10754/666514
    
    Metadata
    Show full item record
    Abstract
    We report a new high electron affinity acceptor end group for organic semiconductors, 2,1,3-benzothiadiazole-4,5,6-tricarbonitrile (TCNBT). An n-type organic semiconductor with an indacenodithiophene (IDT) core and TCNBT end groups was synthesized by a six-fold nucleophilic substitution with cyanides on a fluorinated precursor, itself prepared by a direct arylation approach. This one-step chemical modification was found to significantly impact the molecular properties: the fluorinated precursor, TFBT IDT, a poor ambipolar semiconductor, was converted into TCNBT IDT, a good n-type semiconductor. The highly electron-deficient end group TCNBT dramatically decreased the energy of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO) compared to the fluorinated analogue and improved the molecular orientation when utilized in n-type organic field-effect transistors (OFETs). Solution-processed OFETs based on TCNBT IDT exhibited a charge carrier mobility of up to µ e ≈ 0.15 cm 2 V -1 s -1 with excellent ambient stability for 100 hours, highlighting the benefits of the cyanated end group and the synthetic approach.
    Citation
    Heeney, M., Kafourou, P., Park, B., Luke, J., Luxi, T., Panidi, J., … Kwon, S. (2020). One-step Six-fold Cyanation of Benzothiadiazole Acceptor Units for Air-Stable High-Performance n-Type Organic Field-Effect Transistors. Angewandte Chemie. doi:10.1002/ange.202013625
    Sponsors
    The authors thank the Engineering and Physical Sciences Research Council (EPSRC) (EP/L016702/1 and EP/T028513/1), the Royal Society and the Wolfson Foundation (Royal Society Wolfson Fellowship) for funding. The authors also thank the Global Research Laboratory Program of the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (NRF-2017K1A1A2013153) and the Young Researchers Program of the NRF funded by the Ministry of Science, ICT & Future Planning (NRF-2018R1C1B6006177). This work was also supported by GIST Research Institute (GRI), RISE grant funded by the GIST in 2020. T.D.A. acknowledges the King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research (OSR) under award numbers OSR-2019-CRG8-4095.3, and OSR-2020-CRG8-4095.2. J.L thanks CSEM Brasil for studentship.
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/ange.202013625
    10.1002/anie.202013625
    Additional Links
    https://onlinelibrary.wiley.com/doi/10.1002/ange.202013625
    ae974a485f413a2113503eed53cd6c53
    10.1002/ange.202013625
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Material Science and Engineering Program; KAUST Solar Center (KSC)

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