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Antiaromatic Sapphyrin Isomer: Transformation into Contracted Porphyrinoids with Variable Aromaticity.
- Source :
-
Angewandte Chemie . 1/2/2023, Vol. 135 Issue 1, p1-6. 6p. - Publication Year :
- 2023
-
Abstract
- Sapphyrin is a pentapyrrolic expanded porphyrin with a 22π aromatic character. Herein, we report the synthesis of a 20π antiaromatic sapphyrin isomer 1 by oxidative cyclization of a pentapyrrane precursor P5 with a terminal β‐linked pyrrole. The resulting isomer 1, containing a mis‐linked bipyrrole unit in the skeleton, exhibits a reactivity for further oxidation due to the distinct antiaromatic electronic structure, affording a fused macrocycle 2, possessing a spiro‐carbon‐containing [5.6.5.6]‐tetracyclic structure. Subsequent treatment with an acid afforded a weakly aromatic pyrrolone‐appended N‐confused corrole 3, and thermal fusion gave a [5.6.5.7]‐tetracyclic‐ring‐embedded 14π aromatic triphyrin(2.1.1) analog 4. The cyclization at the mis‐linked pyrrole moiety of P5 played a crucial role in synthesizing the antiaromatic porphyrinoid susceptible to facile transformation to novel porphyrinoids with variable aromaticity. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 135
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 161064047
- Full Text :
- https://doi.org/10.1002/ange.202212174