A simple, inexpensive, and tunable imprinting technique to produce nonporous particles for selective chirally-resolved adsorption of saccharides has been developed. A sugar-based surfactant is added early in the Stöber particle synthesis process (60 seconds after the silica precursor addition) to create molecularly imprinted sites on the surface of the silica particles which are sensitive to the chirality of carbohydrate adsorbates. Mixtures of hexadecyltrimethylammonium bromide (CTAB), and n-octyl-β-d-glucopyranoside (C8G1) or n-dodecyl-β-d-maltopyranoside (C12G2) are employed to target adsorption of d-glucose or d-maltose, respectively. The adsorption of d-glucose on these imprinted materials is enhanced by almost 1.5 times over adsorption of other hexoses like d-mannose and d-galactose which differ by a change at only one chiral center. d-Glucose showed a difference in adsorption of greater than 3 times over the enantiomer l-glucose. Materials imprinted to target d-maltose showed nearly 5 times enhancement in adsorption of d-maltose over cellobiose at the lowest tested concentration. This study shows that a direct molecular imprinting approach of the surface of freshly prepared, soft silica particles can yield particles that exhibit preferential adsorption for a chiral target over similar molecules differing by one or more chiral centers, or by the anomeric attachment within polysaccharides.
|Number of pages||8|
|Journal||New Journal of Chemistry|
|State||Published - 2017|
Bibliographical noteFunding Information:
We thank Jia Ye for help in training and obtaining images with SEM. Development of the surfactant-based imprinting strategy and particle synthesis procedure was carried out as part of a project supported by the National Science Foundation (CBET-0967381/0967390). Characterization of saccharide adsorption and selectivity was carried out as part of a project supported by the U.S. Department of Agriculture Biomass Research and Development Initiative (award numbers 68-3A75-7-608 and 2011-10006-30363).
© 2017 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
ASJC Scopus subject areas
- Chemistry (all)
- Materials Chemistry