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 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry
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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