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

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.

Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application

“…This quite low value of the LUMO level is similar to the values reported for extended carbazoles 28 , indenofluorenes 29 , triarylamine capped polyaromatic hydrocarbons 30 or others. 31 The consequence for such LUMO level, lying clearly below --2 eV, should be an easier electron injection from the cathode during the device operation. 32 Photoelectrical Properties.…”

Synthesis and Absorption Properties of Long Acenoacenes

“…To the best of our knowledge, there are only few scattered examples of class AA-I described in the literature. [15][16][17][18] Very recently, Bunz et al have prepared series of azanalogues of bisanthracene, bistetracene and bispentacene. [19] The synthesis of larger homologues becomes very challenging due to the increasing reactivity with increasing length which is amplified by low solubility in the case of unsubstituted compounds due to strong intermolecular π-π stacking.…”

“…[19] The synthesis of larger homologues becomes very challenging due to the increasing reactivity with increasing length which is amplified by low solubility in the case of unsubstituted compounds due to strong intermolecular π-π stacking. Our approach, enables us to handle these obstacles and was exemplified by synthesis of unsubstituted acenes up to heptacene [20] and very recently by synthesis of unsubstituted [16]starphene. [21] Herein, we report a simple synthesis of catacondensed 2.5-3 nm long non-substituted aromatic acenoacenes 1-3, class AA-I (Figure 2).…”

Effects of interaction between the chelate rings and π‐conjugated systems in fused salphen complexes on UV‐Vis‐NIR spectra

“…The electronic state of a fused aromatic ring system, such as that in a polycyclic aromatic hydrocarbon, is influenced by the connection topology of the rings . Among the polycyclic aromatic hydrocarbons, the acenes have attracted much attention for application to electronic materials because they have a narrower highest occupied molecular orbital (MO)–lowest unoccupied MO (HOMO‐LUMO) gap than the similarly sized phenes and peri‐condensed compounds.…”