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Modulation and binding properties of extended glycoluril molecular clips
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, S-412 96 Gothenburg, Sweden.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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2008 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 32, no 4, 643-651 p.Article in journal (Refereed) Published
Abstract [en]

A glycoluril clip (1) provides a deep cavity for binding of guest molecules. Guest species interact preferentially via hydrogen bonding or ion - lone pair interactions. Complexation-induced conformational modulation of the cavity wall distance was observed. At higher guest - host ratios, inclusion compounds with organic guest molecules are obtained. The X-ray crystallographic structure of 1 center dot(NH4PF6) center dot 3CHCl(3) center dot 2CH(3)OH shows formation of a network of clips connected via polar and non-polar interactions.

Place, publisher, year, edition, pages
2008. Vol. 32, no 4, 643-651 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-96238DOI: 10.1039/b715208fISI: 000254634300008OAI: oai:DiVA.org:uu-96238DiVA: diva2:170744
Available from: 2007-09-26 Created: 2007-09-26 Last updated: 2012-08-03Bibliographically approved
In thesis
1. Exploring Molecular Interactions: Synthesis and Studies of Clip-Shaped Molecular Hosts
Open this publication in new window or tab >>Exploring Molecular Interactions: Synthesis and Studies of Clip-Shaped Molecular Hosts
2007 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Molecular recognition via noncovalent interactions plays a key role in many biological processes such as antigen-antibody interactions, protein folding, the bonding and catalytic transformation of substrates by enzymes, etc. Amongst these noncovalent interactions, electrostatic interactions, hydrogen bonding, π-π interactions, and metal-to-ligand bonding are the most prominent. Exploring noncovalent interactions in host-guest systems that range from small hydrocarbon systems to more complex systems is the main motivation of this thesis. The present study involves the design, synthesis and characterization of clip-shaped molecules as host structures, and an examination of their binding properties with a variety of guests using NMR spectroscopy.

Several clips with a hydrocarbon or glycoluril backbone were synthesized. The binding of cations to small, hydrocarbon-based clips suggests that binding is enhanced by the rigidity and cooperativity between the two sidewalls of the clip. Binding is also very much dependant on the solvent properties.

Glycoluril-based clips built with aromatic sidewalls provide a deep cavity for binding guest molecules. The binding properties of these hosts were studied with several guests such as cations, Lewis acids and Lewis bases. Lewis basic binding sites in the acenaphthene-terminated clip were dominating in guest binding. Complexation-induced conformational changes in the wall-to-wall distance were observed for this clip.

In contrast, for a porphyrin-terminated clip with metal centers, very strong binding to a series of Lewis basic guests of various sizes into the clip cavity was observed. Conformational locking of guests with long alkyl chains was achieved, suggesting that, this clip could be useful as a potential molecular tool for the structural characterization of acyclic molecules with several stereogenic centers. This porphyrin clip was also shown to bind substituted fullerenes in the cavity.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2007. 51 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 344
Keyword
Organic chemistry, Glycoluril clips, host-guest systems, supramolecular chemistry, complexation induced shifts, conformational restriction, NMR spectroscopy, fullerene binding, Organisk kemi
Identifiers
urn:nbn:se:uu:diva-8220 (URN)978-91-554-6973-3 (ISBN)
Public defence
2007-10-18, B7:101, BMC, Husargatan 3, Uppsala, 09:30
Opponent
Supervisors
Available from: 2007-09-26 Created: 2007-09-26 Last updated: 2013-08-30Bibliographically approved

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