Premium
Chiral phosphoric triamide‐based polymers for enantioseparation
Author(s) -
Ahmadabad Fatemeh Karimi,
Pourayoubi Mehrdad,
Bakhshi Hadi
Publication year - 2019
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.48034
Subject(s) - self healing hydrogels , polymer , monomer , methacrylate , materials science , phosphoric acid , polymer chemistry , copolymer , chromatography , organic chemistry , chemistry
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.