Angewandte Chemie International Edition · 2023 · 43 citations · 70 references
Natural SciencesChemistryMaterials ScienceElectronic MaterialsMolecular PhysicsOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic Electronic MaterialsOrganic SemiconductorsOrganic SynthesisAnnulation ReactionsAromatic HeterocyclesAromatic HydrocarbonsHole TransportMagnetic PropertiesPolycyclic Aromatic Hydrocarbon ChemistryPolycyclic Aromatic Hydrocarbon PrecursorsPolycyclic Aromatic Hydrocarbons
Abstract Non‐benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non‐benzenoid isomer of peri ‐tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non‐aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR‐TMS) shows p ‐type semiconducting properties with a hole mobility up to 1.27 cm 2 V −1 s −1 . Moreover, further extension to larger non‐benzenoid PAHs with 19 rings was achieved through on‐surface chemistry from the DAR derivative with one alkynyl group.
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Toward Negatively Curved Carbons
Sai Ho Pun, Qian Miao · Accounts of Chemical Research · 2018 · 449 citations