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BIII 5-Arylsubporphyrins and BIII Subporphine
Koki Kise1, Kota Yoshida1, Ryota Kotani1
1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
Abstract:
Boron(III) 5-arylsubporphyrins and BIII subporphine are promising precursors for functional BIII subporphyrins bearing asymmetric meso-substituents. Herein, we report the first synthesis of these molecules. Among many aryl acid chlorides examined, 4-nitrobenzoyl chloride gave BIII 5-(4-nitrophenyl)subporphyrin in 10 % yield in condensation with triethylamine-tri-N-tripyrromethene-borane. The nitro group of this BIII subporphyrin was reduced with NaBH4 to prepare BIII 5-(aminophenyl)subporphyrin, which was converted into BIII 5-phenylsubporphyrin via the corresponding diazonium salt. BIII subporphine was synthesized by condensation of triethyl orthoformate with triethylamine-tri-N-tripyrromethene-borane. Progressive removal of meso-phenyl substituents leads to continuous changes in the optical properties, whereas the BIII subporphine deviates from this trend in some properties.
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