ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Atropisomers of meso Tetra(N-Mesyl Pyrrol-2-yl) Porphyrins: Synthesis, Isolation and Characterization of All-Pyrrolic Porphyrins.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Unraveling the Pivotal Role of Atropisomerism for Cellular Internalization.Journal of the American Chemical Society · 2022Article
- Elucidating Atropisomerism in Nonplanar Porphyrins with Tunable Supramolecular Complexes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Atropisomers of meso Tetra(N-Mesyl Pyrrol-2-yl) Porphyrins: Synthesis, Isolation and Characterization of All-Pyrrolic Porphyrins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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Abstract
Atropisomerism has been observed in a variety of biaryl compounds and meso-aryl substituted porphyrins. However, in porphyrins, this phenomenon had been shown only with o-substituted 6-membered aromatic groups at the meso-position. We show herein that a 5-membered heteroaromatic (N-mesyl-pyrrol-2-yl) group at the meso-position leads to atropisomerism. In addition, we report a 'one-pot' synthetic route for the synthesis of 'all-pyrrolic' porphyrin (APP) with several N-protection groups (Boc, Cbz, Ms and Ts). Among these groups, we found that only the Ms group gave four individually separable atropisomers of meso-tetra(N-Ms-pyrrol-2-yl) porphyrin. Furthermore, the reductive removal of Cbz- was achieved to obtain meso-tetra(pyrrol-2-yl) porphyrin. Thus, our synthetic procedure provides an easy access to a group of APPs and stable atropisomers, which is expected to expand the application of novel APP-based materials.
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