title: Monosaccharides as Versatile Units for Water-Soluble Supramolecular Polymers.
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.
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
authors.forename: Christianus M A
authors.initials: CM
authors.lastname: Leenders
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
authors.forename: Gijs
authors.initials: G
authors.lastname: Jansen
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
authors.forename: Martijn M M
authors.initials: MM
authors.lastname: Frissen
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
authors.forename: René P M
authors.initials: RP
authors.lastname: Lafleur
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.
authors.forename: Ilja K
authors.identifier: http://orcid.org/0000-0003-3543-4821
authors.initials: IK
authors.lastname: Voets
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands. A.Palmans@tue.nl.
authors.forename: Anja R A
authors.identifier: http://orcid.org/0000-0002-7201-1548
authors.initials: AR
authors.lastname: Palmans
authors.affiliation: Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands. E.W.Meijer@tue.nl.
authors.forename: E W
authors.identifier: http://orcid.org/0000-0003-4126-7492
authors.initials: EW
authors.lastname: Meijer
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D008856:Microscopy, Fluorescence; D009005:Monosaccharides / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D001549:Benzamides; D001896:Boron Compounds; D009005:Monosaccharides; D011108:Polymers; C558700:benzene-1,3,5-tricarboxamide; D014867:Water
keywords: boronic acids; fluorescence spectroscopy; polymers; self-assembly; supramolecular chemistry