Subbiliazine: A contracted phthalocyanine analog

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

doi:10.1021/acs.orglett.0c04291

Subbiliazine: A contracted phthalocyanine analog

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

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

12 Scopus citations

Abstract

The direct borylation of two bis(pyrazolylimino)isoindoline chelates with BF₃ and base under dry conditions results in the formation of two boron adducts. These are ring-contracted analogs of biliazine and can be considered as subbiliazines, as they have bowl-shaped structures similar to subphthalocyanine. Additionally, a new iminooxoisoindoline BF₂ complex was made from hydrolysis of the free base in the presence ofBF₃. The electronic structures of the free bases and subbiliazines were probed by density functional theory (DFT) and time-dependent DFT (TDDFT) methods.

Original language	English
Pages (from-to)	1076-1080
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.0c04291
State	Published - Feb 5 2021
Externally published	Yes

Funding

Generous support from the Minnesota Supercomputing Institute and the University of Tennessee to V.N.N. is greatly appreciated.

Funders	Funder number
University of Tennessee
Minnesota Supercomputing Institute, University of Minnesota

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10.1021/acs.orglett.0c04291

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abstract = "The direct borylation of two bis(pyrazolylimino)isoindoline chelates with BF3 and base under dry conditions results in the formation of two boron adducts. These are ring-contracted analogs of biliazine and can be considered as subbiliazines, as they have bowl-shaped structures similar to subphthalocyanine. Additionally, a new iminooxoisoindoline BF2 complex was made from hydrolysis of the free base in the presence ofBF3. The electronic structures of the free bases and subbiliazines were probed by density functional theory (DFT) and time-dependent DFT (TDDFT) methods.",

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T2 - A contracted phthalocyanine analog

AU - Schrage, Briana R.

AU - Nemykin, Victor N.

AU - Ziegler, Christopher J.

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Y1 - 2021/2/5

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AB - The direct borylation of two bis(pyrazolylimino)isoindoline chelates with BF3 and base under dry conditions results in the formation of two boron adducts. These are ring-contracted analogs of biliazine and can be considered as subbiliazines, as they have bowl-shaped structures similar to subphthalocyanine. Additionally, a new iminooxoisoindoline BF2 complex was made from hydrolysis of the free base in the presence ofBF3. The electronic structures of the free bases and subbiliazines were probed by density functional theory (DFT) and time-dependent DFT (TDDFT) methods.

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JO - Organic Letters

JF - Organic Letters

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ER -

Subbiliazine: A contracted phthalocyanine analog

Abstract

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