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Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond

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Abstract

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.

Graphical abstract: Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond

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Supplementary files

Article information


Submitted
28 Apr 2020
Accepted
21 May 2020
First published
21 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond

B. R. Schrage, V. N. Nemykin and C. J. Ziegler, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03060K

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