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meso ‐Aryl [20]π Homoporphyrin: The Simplest Expanded Porphyrin with the Smallest Möbius Topology
Author(s) -
Anju K. S.,
Das Mainak,
Adinarayana B.,
Suresh Cherumuttathu H.,
Srinivasan A.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709859
Subject(s) - aromaticity , protonation , porphyrin , conjugated system , chemistry , aryl , ring (chemistry) , molecule , topology (electrical circuits) , free base , stereochemistry , ion , photochemistry , organic chemistry , alkyl , mathematics , combinatorics , polymer , salt (chemistry)
An unstable conjugated homoporphyrin was successfully stabilized by introducing meso ‐aryl substitutents. It was evident from the moderate diatropic ring current found by NMR analysis that the newly formed 20π conjugated free base and its protonated form exhibited Möbius aromatic character. Furthermore, complexation as a ligand with an Rh I ion afforded a unique binding mode and retained the Möbius aromaticity. Overall, these compounds are the smallest Möbius aromatic molecules, as confirmed by spectral and crystal‐structure analysis and supported by theoretical studies.