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 |
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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 |
Bibliographical note
Publisher Copyright:© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry