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

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

Research output: Contribution to journalArticle

6 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 languageEnglish
Pages (from-to)2946-2952
Number of pages7
JournalChemistry - An Asian Journal
Volume11
Issue number20
DOIs
Publication statusPublished - 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, 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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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 journalArticle

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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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