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

Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices
Florian GlöcklhoferMiriam M Unterlass

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.

References

Jan 26, 2008·Chemical Communications : Chem Comm·Joshua J McKinnonMark A Spackman
Apr 17, 2010·Chemical Society Reviews·Hagen Klauk
Aug 18, 2010·Advanced Materials·John E AnthonyXiaowei Zhan
Jul 6, 2014·Physical Chemistry Chemical Physics : PCCP·Ke ZhouWenping Hu
Mar 2, 2016·Chemistry : a European Journal·Florian GlöcklhoferJohannes Fröhlich

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Citations

Sep 30, 2017·Advanced Materials·Eun Kwang LeeJoon Hak Oh
Jul 3, 2021·The Journal of Organic Chemistry·Bhargava Rao Billa, Chih-Hsiu Lin
Nov 12, 2020·Journal of the American Chemical Society·Kealan J FallonLuis M Campos

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Methods Mentioned

BETA
X-ray
scanning electron microscopy
scanning
optical microscopy

Software Mentioned

COMPASS

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