Facile Synthetic Approach to a Large Variety of Soluble Diarenoperylenes

Abstract

Fused, extended π-systems such as larger acenes and heteroacenes are interesting compounds for organic thin-film transistors (TFTs). The larger the number of linearly cata-fused rings, the lower the stability of the acenes. By peri-fusion of additional rings, the stabilities can significantly be increased. Here we present a facile approach to use a diborylated dihydroanthracene as precursor to get diareno-fused perylenes in just two steps in high yields. The compounds show pronounced packing in the crystalline states by π-stacking. Promising candidates have been used to fabricate p-channel TFTs by vacuum sublimation showing field-effect mobilities up to 0.12 cm V s .

Benzo‐Fused Perylene Oligomers with up to 13 Linearly Annulated Rings

“…The longest bonds (1.46–1.47 Å) are found at the central ring of the perylene unit, somewhat disconnecting the two halves of the perylene π‐systems, similar as found for perylene itself or other fused perylene compounds [9, 16] . As found before for smaller structures, the red‐highlighted bonds are with 1.36–1.37 Å relatively short and exhibit more olefinic character [9] . According to these data, the π‐electronic structure can be best described as stabilized by seven Clar sextets (Figure 4 b).…”

Functionalized Contorted Polycyclic Aromatic Hydrocarbons by a One‐Step Cyclopentannulation and Regioselective Triflyloxylation

“…Based on our recent results, that diarenoperylenes can be selectively brominated and converted within two steps to tetrarylcoronenes, we treated dibromoperylene ( 1 ) in a palladium‐catalyzed Suzuki–Miyaura cross‐coupling with phenylboronic acid, giving 2 in 91 % yield (Scheme ). Any attempt to photocyclize 2 under oxidative conditions to the parent tetrabenzocoronene 3 failed and only phenyl‐substituted dibenzoperylene 2 was recollected, which is in contrast to the prior successful photocyclization with thiophene‐based precursors .…”

Stabilization by Benzannulation: Butterfly Azaacenes

“…[1a, 6] Although diazaheptacene A has been prepared, it is only persistent in solution-soluble and stable azaheptacenesi solable in the solid state are unknown (Figure1). [7] An alternative way to sta-bilize large azaarenes was shown by Mastalerz andc o-workers, [8] by us, [9] and by others, [10] by disruption of the rectilinear acene backbonew ith pyrene or coronene subunits. In this case, the units separated by,f or example, pyrene or coronene, are isolated aromatic entitiest hat do not interacts trongly with each other.…”