Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.memsci.2009.04.015
Title: Effects of spacer arm length and benzoation on enantioseparation performance of β-cyclodextrin functionalized cellulose membranes
Authors: Zhou, Z.
Xiao, Y. 
Hatton, T.A.
Chung, T.-S. 
Keywords: Chiral separation
Cyclodextrin
Membrane
Spacer arm
Tryptophan
Issue Date: 1-Sep-2009
Source: Zhou, Z., Xiao, Y., Hatton, T.A., Chung, T.-S. (2009-09-01). Effects of spacer arm length and benzoation on enantioseparation performance of β-cyclodextrin functionalized cellulose membranes. Journal of Membrane Science 339 (1-2) : 21-27. ScholarBank@NUS Repository. https://doi.org/10.1016/j.memsci.2009.04.015
Abstract: The enantiomeric resolution performance of cellulose membranes functionalized with chiral layers of beta-cyclodextrin (β-CD) of various spacer arm lengths has been investigated. 6-O-(p-toluenesulfonyl)-β-cyclodextrin (Ts-β-CD) was reacted with ethylenediamine (EDA), diaminopropane (PDA) and diaminobutane (BDA) to synthesize the aminated beta-cyclodextrins EDA-β-CD, PDA-β-CD and BDA-β-CD, respectively, which were subsequently grafted onto partially oxidized cellulose membranes via reductive amination. The enantioselectivity, in racemic tryptophan resolution, increased with decreasing spacer arm length, i.e., αBDA-β-CD < αPDA-β-CD < αEDA-β-CD, while the highest selectivity of 1.20 was obtained when a mixture of chiral selectors was grafted to the membranes. The lower selectivity of membranes grafted with longer spacer arms was attributed to their lower grafting efficiency and, consequently, the presence of more defective regions. Further improvement of enantioselectivity, to ∼1.3-1.5, was realized by substituting the hydroxyl groups on the aminated cyclodextrins with benzoate groups. This increase in enantioselectivity was consistent with molecular modeling predictions of the complex formation energies between the enantiomers and various chiral selectors. © 2009.
Source Title: Journal of Membrane Science
URI: http://scholarbank.nus.edu.sg/handle/10635/88814
ISSN: 03767388
DOI: 10.1016/j.memsci.2009.04.015
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