Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis

Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding const...

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Autores principales: Blom, Magnus, Norrehed, Sara, Andersson, Claes-Henrik, Huang, Hao, Light, Mark E., Bergquist, Jonas, Grennberg, Helena, Gogoll, Adolf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274253/
https://www.ncbi.nlm.nih.gov/pubmed/26703562
http://dx.doi.org/10.3390/molecules21010016
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author Blom, Magnus
Norrehed, Sara
Andersson, Claes-Henrik
Huang, Hao
Light, Mark E.
Bergquist, Jonas
Grennberg, Helena
Gogoll, Adolf
author_facet Blom, Magnus
Norrehed, Sara
Andersson, Claes-Henrik
Huang, Hao
Light, Mark E.
Bergquist, Jonas
Grennberg, Helena
Gogoll, Adolf
author_sort Blom, Magnus
collection PubMed
description Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding constants K(a) = 10(4)–10(6) M(−1) reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.
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spelling pubmed-62742532018-12-28 Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis Blom, Magnus Norrehed, Sara Andersson, Claes-Henrik Huang, Hao Light, Mark E. Bergquist, Jonas Grennberg, Helena Gogoll, Adolf Molecules Article Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding constants K(a) = 10(4)–10(6) M(−1) reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis. MDPI 2015-12-23 /pmc/articles/PMC6274253/ /pubmed/26703562 http://dx.doi.org/10.3390/molecules21010016 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Blom, Magnus
Norrehed, Sara
Andersson, Claes-Henrik
Huang, Hao
Light, Mark E.
Bergquist, Jonas
Grennberg, Helena
Gogoll, Adolf
Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title_full Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title_fullStr Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title_full_unstemmed Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title_short Synthesis and Properties of Bis-Porphyrin Molecular Tweezers: Effects of Spacer Flexibility on Binding and Supramolecular Chirogenesis
title_sort synthesis and properties of bis-porphyrin molecular tweezers: effects of spacer flexibility on binding and supramolecular chirogenesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274253/
https://www.ncbi.nlm.nih.gov/pubmed/26703562
http://dx.doi.org/10.3390/molecules21010016
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