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

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15 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.

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10.1039/d0cc03060k

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title = "Biliazine: A ring open phthalocyanine analog with a: Meso hydrogen bond",

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 - Nemykin, Victor N.

AU - Ziegler, Christopher J.

PY - 2020/6/21

Y1 - 2020/6/21

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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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JO - Chemical Communications

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

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