Mechanistic Study of the Solvent-Dependent Formation of Extended and Stacked Supramolecular Polymers Composed of Bis(imidazolylporphyrinatozinc) Molecules.
allosterism
gel permeation chromatography
polymers
porphyrinoids
supramolecular chemistry
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Jan 2020
13 Jan 2020
Historique:
received:
07
08
2019
revised:
29
09
2019
pubmed:
17
10
2019
medline:
17
10
2019
entrez:
17
10
2019
Statut:
ppublish
Résumé
Bis(imidazolylporphyrinatozinc) molecules linked through a 1,3-butadiynylene moiety respond to the solvents they are dissolved in to afford exclusively extended (E) or stacked (S) supramolecular polymers. This system is expected to be a solvation/desolvation indicator. However, the principles underlying the solvent-dependent formation of the two types of polymers and the mechanism of the transformation between them are unclear. The formation of the polymers is considered to depend on the two types of complementary coordination bonds that can be formed and the π-π interactions between the porphyrins. In this study, the contributions and solvent dependence of both the coordination bonds and the π-π interactions have been investigated. The results clearly indicate that the coordination bonds are weakly or little solvent-dependent, and that the π-π interactions function effectively only in the inner porphyrins of the S-polymer and are strongly solvent-dependent. Thermodynamic analysis revealed that the formation of the E- or S-polymer in solution is determined by the total energies and the type of solvent used. The transformation of the E- to S-polymer was investigated by gel permeation chromatography. The kinetics of the transformation were also determined. The role of the terminal imidazolylporphyrinatozinc moieties was also investigated: The results indicate that the transformation from the E- to S-polymer occurs by an exchange mechanism between the polymers, induced by attack of terminal free imidazolyl groups on a polymer to zinc porphyrins on other polymers.
Identifiants
pubmed: 31618485
doi: 10.1002/chem.201903608
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
669-684Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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