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Phosphate‐Triggered Self‐Assembly of N ‐[(Uracil‐5‐yl)methyl]urea: A Minimalistic Urea‐Derived Hydrogelator
Author(s) -
Kleinsmann Alexander J.,
Weckenmann Nicole M.,
Nachtsheim Boris J.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402916
Subject(s) - urea , uracil , phosphate , molecule , aqueous solution , chemistry , pyrimidine , nuclear magnetic resonance spectroscopy , spectroscopy , polymer chemistry , self assembly , nuclear chemistry , organic chemistry , stereochemistry , biochemistry , dna , physics , quantum mechanics
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.