Organic Letters


Selective Synthesis of Cyclo[9]pyrroles Based on an Oxidative Coupling
23 Jun 2021
A ring-expanded porphyrin with no meso-bridges comprised of an odd number of pyrroles was successfully synthesized via the oxidative coupling of the corresponding terpyrrole. This porphyrin showed a 34pi aromatic character and an intense absorption at the near-infrared region. We analyzed the optical and electronic structures using magnetic circular dichroism spectroscopy and time-dependent density functional theory calculations.
Pyrrole- and Azulene-Fused Azacoronene Dication with 22π+6π Aromatic Rings
17 Oct 2019
Polycyclic heteroaromatic molecules are a highly useful class of organic materials. In this study, synthesis of a new azacoronene, in which both pyrrole and azulene moieties are circularly fused, was achieved in just three steps. This new azacoronene exhibited multistep reversible oxidations under electrochemical and chemical conditions. Formation of an aromatic 22π-electron conjugation and a tropylium cation (6π-electron conjugation) in the dicationic state played a key role in stabilizing this cationic species.


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