Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

Barnaby T Haire; Kane W J Heard; Mark S Little; Adam V S Parry; James Raftery; Peter Quayle; Stephen G Yeates

doi:10.1002/chem.201501861

Non-linear, cata-Condensed, Polycyclic Aromatic Hydrocarbon Materials: A Generic Approach and Physical Properties

Chemistry. 2015 Jul 6;21(28):9970-4. doi: 10.1002/chem.201501861. Epub 2015 Jun 8.

Authors

Barnaby T Haire¹, Kane W J Heard¹, Mark S Little², Adam V S Parry¹, James Raftery¹, Peter Quayle³, Stephen G Yeates⁴

Affiliations

¹ School of Chemistry, University of Manchester, Manchester M13 9PL (UK).
² School of Chemistry, University of Manchester, Manchester M13 9PL (UK). mark.little-2@postgrad.manchester.ac.uk.
³ School of Chemistry, University of Manchester, Manchester M13 9PL (UK). stephen.yeates@manchester.ac.uk.
⁴ School of Chemistry, University of Manchester, Manchester M13 9PL (UK). peter.quayle@manchester.ac.uk.

Abstract

A generic approach to the regiospecific synthesis of halogenated polycyclic aromatics is made possible by the one- or two-directional benzannulation reactions of readily available (ortho-allylaryl)trichloroacetates (the "BHQ" reaction). Palladium-catalysed cross-coupling reactions of the so-formed haloaromatics enable the synthesis of functionalised polycyclic aromatic hydrocarbons (PAHs) with surgical precision. Overall, this new methodology enables the facile mining of chemical space in search of new electronic functional materials.

Keywords: benzannulation; coupling; cyclization; polycycles; polycyclic aromatic hydrocarbons.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.