Biliazine: A ring open phthalocyanine analog with a: Meso hydrogen bond

Briana R. Schrage; Victor N. Nemykin; Christopher J. Ziegler

doi:10.1039/d0cc03060k

Biliazine: A ring open phthalocyanine analog with a: Meso hydrogen bond

Briana R. Schrage, Victor N. Nemykin, Christopher J. Ziegler

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English
Pages (from-to)	6628-6631
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	49
DOIs	https://doi.org/10.1039/d0cc03060k
State	Published - Jun 21 2020
Externally published	Yes

Funding

Generous support from the Minnesota Supercomputing Institute, NSERC, University of Manitoba, and WestGrid Canada to V. N. N. is greatly appreciated.

Funders	Funder number
University of Manitoba
Minnesota Supercomputing Institute, University of Minnesota
Natural Sciences and Engineering Research Council of Canada

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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.",

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AU - Ziegler, Christopher J.

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AB - 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.

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Biliazine: A ring open phthalocyanine analog with a: Meso hydrogen bond

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