Crystallisation-enhanced bulk hole mobility in phenothiazine-based organic semiconductors

D. B. Shinde, Jagadish K. Salunke, Nuno R. Candeias, Tinti Francesca, Gazzano Massimo, P. P. Wadgaonkar, Arri Priimagi, Camaioni Nadia, Paola Vivo

    Research output: Contribution to journalArticleScientificpeer-review

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    Abstract

    A series of three novel donor-acceptor systems based on C(3)-malononitrile-substituted phenothiazines was synthesised in good overall yields and their thermal, spectroscopic, and electrochemical properties were characterised. The compounds were prepared through a sequence of Ullmann-coupling, Vilsmeier-Haack formylation and Knoevenagel-condensation, followed by Suzuki-coupling reactions for introduction of aryl substitutents at C(7) position of the phenothiazine. The introduction of a donor unit at the C(7) position exhibited a weak impact on the optical and electrochemical characteristics of the compounds and led to amorphous films with bulk hole mobilities in the typical range reported for phenothiazines, despite the higher charge delocalisation as attested by computational studies. In contrast, highly ordered films were formed when using the C(7)-unsubstituted 3-malononitrile phenothiazine, exhibiting an outstanding mobility of 1 × 10−3 cm2 V−1 s−1, the highest reported for this class of compounds. Computational conformational analysis of the new phenothizanes suggested that free rotation of the substitutents at the C(7) position suppresses the ordering of the system, thereby hampering suitable packing of the new materials needed for high charge carrier mobility.
    Original languageEnglish
    Article number46268
    Number of pages10
    JournalScientific Reports
    Volume7
    DOIs
    Publication statusPublished - 12 Apr 2017
    Publication typeA1 Journal article-refereed

    Publication forum classification

    • Publication forum level 2

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