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- Title
B<sup>III</sup> 5‐Arylsubporphyrins and B<sup>III</sup> Subporphine.
- Authors
Kise, Koki; Yoshida, Kota; Kotani, Ryota; Shimizu, Daiki; Osuka, Atsuhiro
- 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. Rotational relaxation: BIII 5‐arylsubporphyrins and BIII subporphine were synthesized for the first time by the condensation reactions of triethylamine‐tri‐N‐tripyrromethene‐borane with aryl acid chloride and ethyl orthoformate, respectively. Removal of meso‐phenyl substituents leads to progressive changes in the optical properties up to BIII 5‐arylsubporphyrin but BIII subporphine deviates from this trend (see figure).
- Subjects
BORON; PORPHYRINS; ACYL chlorides; NITROPHENYL compounds; TRIETHYLAMINE; BORANES
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 72, p19136
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201801491