Synthesis of non- or antiaromatic conjugated macrocycles

A ring-expanded porphyrin, diazuliamethyrin, was successfully synthesized via a “3+3” condensation method. This porphyrin showed a 24pi non- or antiaromatic character. We analyzed the optical and electronic structures using magnetic circular dichroism spectroscopy and time-dependent density functional theory calculations.

Synthesis of diazuliamethyrin

Synthesis of diazuliamethyrin

Profs. Okujima and Uno, in collaboration with Prof. Kobayashi at Shinshu University, reported  their success in the synthesis of diazuliamethyrin, a core-modified hexaphyrin(, and descibed its molecular structure, electronic structure and optical properties.

Amethyrin is a stable and antiaromatic ring-expanded porphyrin comprised of 6 pyrroles and 2 meso-bridged carbons. We successfully synthesized diazuliamethyrin via a “3+3” porphyrin synthesis. We confirmed it to have a 24pi non- or antiaromatic character by NMR, absorption, and MCD spectra analyses, and by TD-DFT calculations. Our findings were published on December 21, 2021 in Organic Letters.

Published: 23 Jan 2022


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