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Highly-stable, green-solvent-processable organic thin-film transistors: angular- vs linear-shaped carbazoledioxazine derivatives

Abstract

The design and synthesis of new dye/pigment-based semiconductors have made a significant contribution to the development of organic electronics. However, there are few detailed studies about the comparison of isomeric dye/pigment molecules, which play an important role in revealing the molecular structure-property-device performance relationships. In this study, we, for the first time, compared the thermal stability, optical, electrochemical, molecular assembling and charge transport properties of isomeric angular and linear-shaped carbazoledioxazine derivatives, namely Ang-CZ and Lin-CZ, respectively. While the molecular shapes hardly affect the optical bandgaps and energy levels, they dramatically alter the charge transport characteristics. Accordingly, Lin-CZ demonstrated a two orders of magnitude higher mobility than Ang-CZ, evaluated by thin-film transistors (TFTs). Further studies suggested that Lin-CZ tends to adopt a denser molecular packing motif and higher molecular orbital overlapping than Ang-CZ revealed by grazing-incidence wide-angle X-ray scattering (GIWAXS), atomic force microscopy (AFM), and density functional theory calculations (DFT). More importantly, Lin-CZ-T, a π-extended derivative of Lin-CZ, showed a relatively high and stable TFT mobility over 0.1 cm2 V−1 s−1 by using an environmentally-benign solvent and pre-aggregation method. Our findings will provide direction to developing more promising molecular semiconductors and organic TFT technology.

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Supplementary files

Publication details

The article was received on 12 Apr 2018, accepted on 08 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8TC01711E
Citation: J. Mater. Chem. C, 2018, Accepted Manuscript
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    Highly-stable, green-solvent-processable organic thin-film transistors: angular- vs linear-shaped carbazoledioxazine derivatives

    Y. Wang, H. Tatsumi, R. Otsuka, T. Mori and T. Michinobu, J. Mater. Chem. C, 2018, Accepted Manuscript , DOI: 10.1039/C8TC01711E

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