title: Phosphate-triggered self-assembly of N-[(Uracil-5-yl)methyl]urea: a minimalistic urea-derived hydrogelator.
abstract: N-[(Uracil-5-yl)methyl]urea is reported as a minimalistic low-molecular-weight hydrogelator (LMWHG). The unusual phosphate-induced assembly of this compound has been thoroughly investigated by IR, UV/Vis, and NMR spectroscopy, electron microscopy, and rheological experiments. This rare example of an anion-triggered urea-based LMWHG is the first example of a pyrimidine- and urea-containing molecule that can be forced into self-assembly in aqueous solution without additional aromatic or lipophilic groups. The gelator/phosphate ratio within the hydrogel was successfully determined by (31) P MAS NMR spectroscopy. The hydrogel exhibits a very fast and repeatable self-healing property, and remarkable G' values. The viscoelastic properties of the hydrogel can easily be tuned by variation of the phosphate ratio.
authors.affiliation: Institut für Organische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany).
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Kleinsmann
authors.forename: Nicole M
authors.initials: NM
authors.lastname: Weckenmann
authors.forename: Boris J
authors.initials: BJ
authors.lastname: Nachtsheim
mesh_terms: D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D010710:Phosphates / Q000737:chemistry*; D012212:Rheology / Q000379:methods; D013057:Spectrum Analysis; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D010710:Phosphates; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate; D014498:Uracil; D014508:Urea
keywords: gels; hydrogen bonds; nucleobases; self-assembly; urea