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Issue 4, 2018
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Molecular ordering of A(D–A′–D)2-based organic semiconductors through hydrogen bonding after simple cleavage of tert-butyloxycarbonyl protecting groups

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Abstract

We have successfully achieved the molecular ordering of semiconducting small molecules comprising a newly designed A(D–A′–D)2 system. The A(D–A′–D)2 small molecules have two different acceptors based on isoindigo and diketopyrrolopyrrole along with tert-butoxycarbonyl (t-Boc) groups and hexyl chains, which improve the solubility of the materials. After simple thermal annealing, the t-Boc groups were removed to allow strong hydrogen bonds between N–H⋯C[double bond, length as m-dash]O to form, and this resulted in improved molecular ordering of the organic semiconductors. The crystalline morphology was confirmed by X-ray diffraction coupled with high-voltage electron microscopy, and the resulting materials showed improved hole mobilities. In this work, the effect of the incorporation of t-Boc groups onto A(D–A′–D)2-based organic semiconductors on their morphological and electrical properties was evaluated.

Graphical abstract: Molecular ordering of A(D–A′–D)2-based organic semiconductors through hydrogen bonding after simple cleavage of tert-butyloxycarbonyl protecting groups

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Publication details

The article was received on 15 Nov 2017, accepted on 07 Jan 2018 and first published on 08 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04440B
Citation: New J. Chem., 2018,42, 2557-2563
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    Molecular ordering of A(D–A′–D)2-based organic semiconductors through hydrogen bonding after simple cleavage of tert-butyloxycarbonyl protecting groups

    C. K. Trinh, H. Lee, J. W. Choi, M. Shaker, W. Kim and J. Lee, New J. Chem., 2018, 42, 2557
    DOI: 10.1039/C7NJ04440B

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