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

7 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

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Nitration

Discrete Fourier transforms

Electronic properties

Conformations

Spectrum Analysis

Nuclear magnetic resonance

Oxidation

All Science Journal Classification (ASJC) codes

Chemistry(all)
Biochemistry
Organic Chemistry

Cite this

Shimizu, D., Lee, S. K., Kim, D., & Osuka, A. (2016). meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s. Chemistry - An Asian Journal, 11(20), 2946-2952. https://doi.org/10.1002/asia.201601019

Shimizu, Daiki ; Lee, Seung Kyu ; Kim, Dongho ; Osuka, Atsuhiro. / meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s. In: Chemistry - An Asian Journal. 2016 ; Vol. 11, No. 20. pp. 2946-2952.

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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.",

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Shimizu, D, Lee, SK, Kim, D & Osuka, A 2016, 'meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s', Chemistry - An Asian Journal, vol. 11, no. 20, pp. 2946-2952. https://doi.org/10.1002/asia.201601019

meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s. / Shimizu, Daiki; Lee, Seung Kyu; Kim, Dongho; Osuka, Atsuhiro.

In: Chemistry - An Asian Journal, Vol. 11, No. 20, 20.10.2016, p. 2946-2952.

Research output: Contribution to journal › Article

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AU - Shimizu, Daiki

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AU - Kim, Dongho

AU - Osuka, Atsuhiro

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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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Shimizu D, Lee SK, Kim D, Osuka A. meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso Azosubporphyrinatoboron(III)s. Chemistry - An Asian Journal. 2016 Oct 20;11(20):2946-2952. https://doi.org/10.1002/asia.201601019

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10.1002/asia.201601019