Triangle‐Shaped Polycyclic Aromatic Hydrocarbons

Abstract

Dreiecke und Zickzackketten: Große C3‐symmetrische polycyclische aromatische Kohlenwasserstoffe mit Dreieckform und mehrfachen Zickzack‐Peripherien wurden synthetisiert. Die Mesophasen der Moleküle sind als Folge der helicalen Packung über einen großen Temperaturbereich stabil. Des Weiteren wurde bei einer der größeren Strukturen ein zweidimensionales Wabenmuster beobachtet (siehe Bild).

Temperature‐Enhanced Solvent Vapor Annealing of a C3 Symmetric Hexa‐peri‐Hexabenzocoronene: Controlling the Self‐Assembly from Nano‐ to Macroscale

“…M1 was synthesized as described in Reference 41 following a synthetic procedure readapted from Reference 56. Synthesis of M2 molecule has been already published 67.…”

“…As a model system to explore the TESVA technique, we used substituted hexa‐ peri ‐hexabenzocoronenes (HBCs) 37–45. HBCs (Figure 1) are polycyclic aromatic hydrocarbons, which are well known for their unique propensity to self‐assemble into ordered columnar π – π stacked architectures, whose formation is favored both by the π – π interactions between the large aromatic cores and the phase separation, on the subnanometer scale, between the flexible substituents and rigid aromatic center 38, 46, 47.…”

Synthesis of Polyaromatic Hydrocarbons from Bis(biaryl)diynes: Large PAHs with Low Clar Sextets

“…Due to the fully populated Clar p sextets, [4] the reported large PAHs typically have irreducible highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO-LUMO) energy gaps (E g > 2.1 eV), [2,3] in addition to difficulties of functionalization. Large PAHs with fewer aromatic p sextets would not only facilitate electron delocalization to create small energy gaps, [5] but also generate an open-shell ground state with singlet or triplet biradicals.…”

“…[1] The reported large PAHs were generally prepared from the Scholl oxidation of 1,2-diphenylbenzene units; several representatives [2,3] I-V are depicted in Scheme 1. Due to the fully populated Clar p sextets, [4] the reported large PAHs typically have irreducible highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO-LUMO) energy gaps (E g > 2.1 eV), [2,3] in addition to difficulties of functionalization.…”

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Large polyaromatic hydrocarbons (PAHs) have found various applications in organic opto-electronic devices. [1] The reported large PAHs were generally prepared from the Scholl oxidation of 1,2-diphenylbenzene units; several representatives [2,3]

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