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Chemistry. 2017 May 23;23(29):7066-7073. doi: 10.1002/chem.201700421. Epub 2017 May 02.

Dicyano-Substituted Diazaacenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Matthias Müller, Stella S Beglaryan, Silke Koser, Sebastian Hahn, Olena Tverskoy, Frank Rominger, Uwe H F Bunz

Affiliations

  1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

PMID: 28295719 DOI: 10.1002/chem.201700421

Abstract

Herein, we report the synthesis, spectroscopic, and structural properties of novel 2,3-dicyano-substituted azaacenes containing three to six annelated rings as a framework. The targets were prepared by Pd-catalyzed coupling of diamino-bis(tri-isopropylsilylethynyl)benzene, -naphthalene, and -anthracene with either 4,5-dibromophthalonitrile or 6,7-dibromonaphthalene-2,3-dicarbonitrile into the respective N,N'-dihydrodiazaacenes. Oxidation with MnO

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Pd-catalyzed coupling; azaacenes; cyanides; density functional calculations; n-type semiconductors

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