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Issue 10, 2017
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Dicyano- and tetracyanopentacene: foundation of an intriguing new class of easy-to-synthesize organic semiconductors

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Abstract

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.

Graphical abstract: Dicyano- and tetracyanopentacene: foundation of an intriguing new class of easy-to-synthesize organic semiconductors

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Publication details

The article was received on 10 Jan 2017, accepted on 16 Feb 2017 and first published on 16 Feb 2017


Article type: Paper
DOI: 10.1039/C7TC00143F
Citation: J. Mater. Chem. C, 2017,5, 2603-2610
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    Dicyano- and tetracyanopentacene: foundation of an intriguing new class of easy-to-synthesize organic semiconductors

    F. Glöcklhofer, A. Petritz, E. Karner, M. J. Bojdys, B. Stadlober, J. Fröhlich and M. M. Unterlass, J. Mater. Chem. C, 2017, 5, 2603
    DOI: 10.1039/C7TC00143F

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