Dicarba[26]hexaporphyrinoids(1.1.1.1.1.1) with an Embedded Cyclopentene Moiety—Conformational Switching

Incorporation of cyclopentene fragments into a skeleton of parental [26]hexaphyrin(1.1.1.1.1.1) afforded extended carbaporphyrinoids: 31,34‐dicarbahexa[26]chlorin and its derivatives: the first externally substituted by ethoxy and 2,4,6‐trimethylbenzylidene groups and the second one formed by select...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-09, Vol.26 (54), p.12322-12327
Main Authors: Berlicka, Anna, Stanowska, Justyna, Białek, Michał J., Ślepokura, Katarzyna, Latos‐Grażyński, Lechosław
Format: Article
Language:English
Subjects:
carbaporphyrinoid
conformational switching
expanded porphyrin
macrocycles
porphyrinoid
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Summary:Incorporation of cyclopentene fragments into a skeleton of parental [26]hexaphyrin(1.1.1.1.1.1) afforded extended carbaporphyrinoids: 31,34‐dicarbahexa[26]chlorin and its derivatives: the first externally substituted by ethoxy and 2,4,6‐trimethylbenzylidene groups and the second one formed by selective oxidation of one cyclopentene ring. Macrocycles adopt dumbbell‐shaped conformations with two meso hydrogen atoms located inside the macrocyclic cavity. Protonation of 31,34‐dicarba[26]hexachlorins provided dications existing in dumbbell‐shaped and rectangular conformations. Flexible expanded carbaporphyrinoids: Dicarba[26]hexachlorins embedding cyclopentene and cyclopentadiene units acquired a dumbbell‐shaped conformation. Nevertheless, protonation triggered rearrangements, involving a peculiar inversion of carbocyclic rings, afforded a rectangular geometry.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202002603