Monosaccharides as versatile units for water-soluble supramolecular polymers

C.M.A. Leenders, G. Jansen, M.M.M. Frissen, R.P.M. Lafleur, I.K. Voets, A.R.A. Palmans, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

17 Citations (Scopus)
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Abstract

We introduce monosaccharides as versatile water-soluble units to compatibilise supramolecular polymers based on the benzene-1,3,5-tricarboxamide (BTA) moiety with water. A library of monosaccharide-based BTAs is evaluated, varying the length of the alkyl chain (hexyl, octyl, decyl and dodecyl) separating the BTA and saccharide units, as well as the saccharide units (α-glucose, β-glucose, α-mannose and α-galactose). In all cases, the monosaccharides impart excellent water compatibility. The length of the alkyl chain is the determining factor to obtain either long, one-dimensional supramolecular polymers (dodecyl spacer), small aggregates (decyl spacer) or molecularly dissolved (octyl and hexyl) BTAs in water. For the BTAs comprising a dodecyl spacer, our results suggest that a cooperative self-assembly process is operative and that the introduction of different monosaccharides does not significantly change the self- assembly behaviour. Finally, we investigate the potential of post-assembly functionalisation of the formed supramolecular polymers by taking advantage of dynamic covalent bond formation between the monosaccharides and benzoxaboroles. We observe that the supramolecular polymers readily react with a fluorescent benzoxaborole derivative permitting imaging of these dynamic complexes by confocal fluorescence microscopy.

Original languageEnglish
Pages (from-to)4608-4615
Number of pages8
JournalChemistry : A European Journal
Volume22
Issue number13
DOIs
Publication statusPublished - 18 Mar 2016

Keywords

  • boronic acids
  • fluorescence spectroscopy
  • polymers
  • self-assembly
  • supramolecular chemistry

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