Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 10, 2017

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

Author affiliations

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

Supplementary files

Article information


Submitted
10 Jan 2017
Accepted
16 Feb 2017
First published
16 Feb 2017

This article is Open Access

J. Mater. Chem. C, 2017,5, 2603-2610
Article type
Paper

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements