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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
Published on: August 2, 2012
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Monosaccharides as Versatile Units for Water-Soluble Supramolecular Polymers
Christianus M A Leenders1, Gijs Jansen1, Martijn M M Frissen1
1Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 19, 2016
Summary
Monosaccharides enhance water compatibility in benzene-1,3,5-tricarboxamide (BTA) supramolecular polymers. Alkyl chain length controls assembly into polymers, aggregates, or dissolved states, enabling functionalization for imaging.
Area of Science:
- Supramolecular Chemistry
- Polymer Science
- Carbohydrate Chemistry
Background:
- Benzene-1,3,5-tricarboxamide (BTA) moieties form supramolecular polymers through hydrogen bonding.
- Achieving water solubility for hydrophobic BTA-based systems is a significant challenge.
- Monosaccharides offer a potential solution due to their inherent hydrophilicity.
Purpose of the Study:
- To develop water-compatible supramolecular polymers using monosaccharide functionalization of BTA.
- To investigate the influence of alkyl spacer length and specific monosaccharide types on self-assembly in water.
- To explore the post-assembly functionalization capabilities of these novel supramolecular materials.
Main Methods:
- Synthesis of a library of monosaccharide-functionalized BTA derivatives with varying alkyl chain lengths (hexyl to dodecyl) and saccharide units (glucose, mannose, galactose).
- Characterization of self-assembly behavior in aqueous solutions using techniques sensitive to aggregate size and structure.
- Investigation of dynamic covalent chemistry for post-assembly functionalization with fluorescent benzoxaboroles.
Main Results:
- All synthesized monosaccharide-based BTAs demonstrated excellent water compatibility.
- Alkyl chain length was the critical factor determining the assembly state: dodecyl spacers formed 1D polymers, decyl spacers formed aggregates, and octyl/hexyl spacers resulted in molecular dissolution.
- Self-assembly of dodecyl-spaced BTAs proceeded via a cooperative mechanism, largely independent of the specific monosaccharide used.
- Post-assembly reaction with a fluorescent benzoxaborole enabled successful imaging of the supramolecular polymers via confocal fluorescence microscopy.
Conclusions:
- Monosaccharide functionalization is a highly effective strategy for rendering BTA supramolecular polymers water-soluble.
- Precise control over supramolecular architecture in water can be achieved by tuning the alkyl spacer length.
- The dynamic nature of these supramolecular polymers allows for straightforward functionalization, opening avenues for advanced applications such as bioimaging.
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