Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 4, Pages 1130-1136Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200400677
Keywords
carboxylic acids; copolymerization; gels; pH response; supramolecular chemistry
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A pH-respoDsive volume-change function was successfully introduced into a supramolecular hydrogel that contained GaINAc-appended (GaINAc=N-acetylgalactosamine) glutamate ester 1 by the simple mixing of it with an appropriate amount of 2a or 2b amphiphilic carboxylic acid. In the 1:1 mixture (1:2), the hydrogel swelled under neutral pH conditions, but shrank to almost half of its original volume under acidic pH conditions. ne structure and pH response of the mixed hydrogel were characterized by using X-ray diffraction (XRD), confocal laser scanning microscopy (CLSM), transmission or scanning electron microscopy (TEM, SEM), and Fourier transform IR (FTIR) spectroscopy. Well-developed fibers formed a stable hydrogel by self-assembly, and under acidic conditions the charge of the carboxylic acid terminal (from the carboxylate anion) was neutralized and then these fibers became densely packed. This macroscopic pH response was also applied to the pH-triggered release of bioactive substances. In this mixed supramolecular hydrogel, the hydrogelator I provides a stable hydrogel structure and the additive 2 acts as a commander that is sensitive to an environmental pH signal. The present supramolecular copolymerization strategy should be useful for the construction of novel, stimuli-responsive, soft materials.
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