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

8 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

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this