meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s

Daiki Shimizu; Seung Kyu Lee; Dongho Kim; Atsuhiro Osuka

doi:10.1002/asia.201601019

meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s

Daiki Shimizu, Seung Kyu Lee, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

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

9 Citations (Scopus)

Abstract

meso-Nitrosubporphyrinatoboron(III) was synthesized by nitration of meso-free subporphyrin with AgNO₂/I₂. The subsequent reduction with a combination of NaBH₄ and Pd/C gave meso-aminosubporphyrinatoboron(III). meso-Nitro- and meso-amino-groups significantly influenced the electronic properties of subporphyrin, which has been confirmed by NMR and UV/Vis spectra, electrochemical analysis, and DFT calculations. Oxidation of meso-aminosubporphyrinatoboron(III)s with PbO₂ cleanly gave meso-to-meso azosubporphyrinatoboron(III)s that exhibited almost coplanar conformations and large electronic interaction through the azo-bridge.

Original language	English
Pages (from-to)	2946-2952
Number of pages	7
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	20
DOIs	https://doi.org/10.1002/asia.201601019
Publication status	Published - 2016 Oct 20

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Biochemistry
Organic Chemistry

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10.1002/asia.201601019

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title = "meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s",

abstract = "meso-Nitrosubporphyrinatoboron(III) was synthesized by nitration of meso-free subporphyrin with AgNO2/I2. The subsequent reduction with a combination of NaBH4 and Pd/C gave meso-aminosubporphyrinatoboron(III). meso-Nitro- and meso-amino-groups significantly influenced the electronic properties of subporphyrin, which has been confirmed by NMR and UV/Vis spectra, electrochemical analysis, and DFT calculations. Oxidation of meso-aminosubporphyrinatoboron(III)s with PbO2 cleanly gave meso-to-meso azosubporphyrinatoboron(III)s that exhibited almost coplanar conformations and large electronic interaction through the azo-bridge.",

author = "Daiki Shimizu and Lee, {Seung Kyu} and Dongho Kim and Atsuhiro Osuka",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s

AU - Shimizu, Daiki

AU - Lee, Seung Kyu

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2016/10/20

Y1 - 2016/10/20

N2 - meso-Nitrosubporphyrinatoboron(III) was synthesized by nitration of meso-free subporphyrin with AgNO2/I2. The subsequent reduction with a combination of NaBH4 and Pd/C gave meso-aminosubporphyrinatoboron(III). meso-Nitro- and meso-amino-groups significantly influenced the electronic properties of subporphyrin, which has been confirmed by NMR and UV/Vis spectra, electrochemical analysis, and DFT calculations. Oxidation of meso-aminosubporphyrinatoboron(III)s with PbO2 cleanly gave meso-to-meso azosubporphyrinatoboron(III)s that exhibited almost coplanar conformations and large electronic interaction through the azo-bridge.

AB - meso-Nitrosubporphyrinatoboron(III) was synthesized by nitration of meso-free subporphyrin with AgNO2/I2. The subsequent reduction with a combination of NaBH4 and Pd/C gave meso-aminosubporphyrinatoboron(III). meso-Nitro- and meso-amino-groups significantly influenced the electronic properties of subporphyrin, which has been confirmed by NMR and UV/Vis spectra, electrochemical analysis, and DFT calculations. Oxidation of meso-aminosubporphyrinatoboron(III)s with PbO2 cleanly gave meso-to-meso azosubporphyrinatoboron(III)s that exhibited almost coplanar conformations and large electronic interaction through the azo-bridge.

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meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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