Chiral phosphoric triamide‐based polymers for enantioseparation

• Published in: Journal of applied polymer science 2019-11, Vol.136 (41), p.n/a
• Main Authors: Ahmadabad, Fatemeh Karimi, Pourayoubi, Mehrdad, Bakhshi, Hadi
• Format: Article
• Language: English
• Subjects: Alanine; Beads; Filling; Hydrogels; Materials science; Monomers; Optical isomers; Phenylalanine; Polymers; Separation; Tartaric acid; Valine
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.48034

ABSTRACT Novel optical isomers of phosphoramide‐methacrylate monomers were synthesized and used for the preparation of corresponding polymers and hydrogels as chiral absorbents. In order to direct enantioseparation, two simple and inexpensive methods were designed: (a) immobilization of the chiral polymers on glass beads as packing material for the separation columns and (b) filling of chiral hydrogels in tea bags to fabricate separation bags. The specific rotations for R‐ and S‐monomers were + 22.0° and − 21.8°, while those for R‐ and S‐polymers were + 20.8° and − 22.1°, respectively. The enantioseparation of (±)‐α‐methylbenzylamine, DL‐alanine, DL‐valine, DL‐tartaric acid, DL‐phenylalanine, and omeprazole was evaluated. The maximum enantioseparation (optical purity) of 97% was observed for (±)‐α‐methylbenzylamine by S‐hydrogel. Chiral hydrogels resulted in enantioseparations with higher purities (up to 97%) comparing to the chiral polymers, but in longer times (2–3 days). The desorption process easily occurred from the absorbed columns or bags. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48034.