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Issue 3, 2013
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Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics

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Abstract

Fourteen new derivatives of 9,10-anthraquinone or 9,10-dimethoxyanthracene were designed, synthesised and characterised. Regarding the structure, the compounds are π-conjugated (cross and linear, respectively) and feature thiophene terminated side arms attached to five different positions of the anthraquinone or anthracene core. The synthesis of the compounds involves a cross-coupling procedure in the key reaction steps. Crystal structures of compounds 5 and 19 have been studied. The thiophene containing title compounds 1–5 can be reduced and oxidised by a two step redox process. The electrochemical parameters have been analysed by cyclic voltammetry (CV). Theoretical calculations in the framework of all-electron density functional theory (DFT) were used to investigate the electronic structure of the individual free molecules. Furthermore, calculations of the transport properties of model devices containing compounds 1–3 and respective reduced hydroquinone derivatives assembled at Au(111) electrodes were carried out to evaluate their potential for the application as redox-active switches.

Graphical abstract: Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics

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Supplementary files

Article information


Submitted
30 Aug 2012
Accepted
26 Nov 2012
First published
27 Nov 2012

New J. Chem., 2013,37, 601-610
Article type
Paper

Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics

N. Seidel, T. Hahn, S. Liebing, W. Seichter, J. Kortus and E. Weber, New J. Chem., 2013, 37, 601
DOI: 10.1039/C2NJ40772H

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