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Covalently Linked Bis(Amido-Corroles): Inter- and Intramolecular Hydrogen-Bond-Driven Supramolecular Assembly

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dc.abstract.enFour bis-corroles linked by diamide bridges were synthesized through peptide-type coupling of a trans-A2Bcorrole acid with aliphatic and aromatic diamines. In the solid state, the hydrogen-bond pattern in these bis-corroles is strongly affected by the type of solvent used in the crystallization process. Although intramolecular hydrogen bonds play a decisive role, they are supported by intermolecular hydrogen bonds and weak NH···p interactions between molecules of toluene and the corrole cores. In an analogy to mono(amido-corroles), both in crystalline state and in solutions, the aliphatic or aromatic bridge is located directly above the corrole ring. When either ethylenediamine or 2,3- diaminonaphthalene are used as linkers, incorporation of polar solvents into the crystalline lattice causes a roughly parallel orientation of the corrole rings. At the same time, both NHCO···NH corrole hydrogen bonds are intramolecular. In contrast, solvation in toluene causes a distortion with one of the hydrogen bonds being intermolecular. Interestingly, intramolecular hydrogen bonds are always formed between the –NHCO– functionality located further from the benzene ring present at the position 10-meso. In solution, the hydrogen- bonds pattern of the bis(amido-corroles) is strongly affected by the type of the solvent. Compared with toluene (strongly high-field shifted signals), DMSO and pyridine disrupt self-assembly, whereas hexafluoroisopropanol strengthens intramolecular hydrogen bonds.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCyrański, Michał
dc.contributor.authorOrłowski, Rafał
dc.contributor.authorSCHILF, Wojciech
dc.contributor.authorGryko, Daniel
dc.contributor.authorSTASZEWSKA-KRAJEWSKA, Olga
dc.contributor.authorCichowicz, Grzegorz
dc.date.accessioned2024-01-24T20:54:05Z
dc.date.available2024-01-24T20:54:05Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.number41
dc.description.volume25
dc.identifier.doi10.1002/CHEM.201901254
dc.identifier.issn0947-6539
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/103846
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemistry - A European Journal
dc.relation.pages9658-9664
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleCovalently Linked Bis(Amido-Corroles): Inter- and Intramolecular Hydrogen-Bond-Driven Supramolecular Assembly
dc.typeJournalArticle
dspace.entity.typePublication