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 | |
| Publication status | Published - 2016 Oct 20 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Biochemistry
- Organic Chemistry
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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 journal › Article
TY - JOUR
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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U2 - 10.1002/asia.201601019
DO - 10.1002/asia.201601019
M3 - Article
AN - SCOPUS:84987616085
VL - 11
SP - 2946
EP - 2952
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 20
ER -