@article{Glocklhofer2017-03-14Dicya-54954,
  year={2017},
  doi={10.1039/c7tc00143f},
  title={Dicyano- and tetracyanopentacene : foundation of an intriguing new class of easy-to-synthesize organic semiconductors},
  number={10},
  volume={5},
  issn={2050-7526},
  journal={Journal of Materials Chemistry C: Materials for Optical and Electronic Devices},
  pages={2603--2610},
  author={Glöcklhofer, Florian and Petritz, Andreas and Karner, Esther and Bojdys, Michael J. and Stadlober, Barbara and Fröhlich, Johannes and Unterlass, Miriam M.}
}

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    <dc:creator>Glöcklhofer, Florian</dc:creator>
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    <dcterms:abstract xml:lang="eng">Cyanated pentacenes are very promising candidate materials for ambipolar and n-type transistors. However, only a few examples have been obtained to date - all requiring lengthy, multi-step processes. Herein, we present the first preparation of 5,7,12,14-tetracyanopentacene (TCP) and a facile, scaled-up preparation of 6,13-dicyanopentacene (DCP). Both compounds are prepared by a one-pot synthesis using cheap quinones as starting materials. Detailed crystallographic investigations evince that the bulk assemblies of both cyanated pentacenes are dominated by non-covalent interactions, resulting in a dense, stable, face-to-face packing and in an intriguing packing motif for TCP. Very low frontier molecular orbital energy levels and a reversible bleaching of TCP are revealed by cyclic voltammetry. Finally, both cyanated pentacenes are used in proof-of-concept organic thin-film transistors (OTFTs) operating under ambient conditions. This work highlights the potential of cyanation for larger acenes and presents a straightforward route to the rational design of this promising class of materials.</dcterms:abstract>
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    <dc:contributor>Stadlober, Barbara</dc:contributor>
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    <dc:contributor>Unterlass, Miriam M.</dc:contributor>
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    <dc:contributor>Karner, Esther</dc:contributor>
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    <dc:contributor>Fröhlich, Johannes</dc:contributor>
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