Schrage Briana R, Nemykin Victor N, Ziegler Christopher J
Department of Chemistry, The University of Akron Akron, Ohio, 44312-3601, USA.
Department of Chemistry, The University of Manitoba Winnipeg, Manitoba R3T 2N2, Canada.
Chem Commun (Camb). 2020 Jun 18;56(49):6628-6631. doi: 10.1039/d0cc03060k.
The hemiporphyrazine type chelate and phthalocyaninine analog biliazine (H2BlzH) and its metal complexes can be synthesized in one-step from a monosubstituted diiminisoindoline (DII). This singly substituted precursor is produced from the reaction of unsubstituted DII and 2-aminopyrazole. The biliazine macrocycle is a tetradentate chelate where the ring is closed via a strong hydrogen bond at the meso position. Although the hydrogen bond closes the ring, there is little evidence for 18-electron type annulene aromaticity across the macrocycle, as seen in the UV-visible and MCD spectra and supported by DFT calculations.
