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Chiral Polymers of Intrinsic Microporosity: Selective Membrane Permeation of Enantiomers
Author(s) -
Weng Xilun,
Baez José E.,
Khiterer Mariya,
Hoe Madelene Y.,
Bao Zongbi,
Shea Kenneth J.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504934
Subject(s) - permeation , chemistry , membrane , enantiomer , polymer , diastereomer , hydrolysis , chromatography , solvent , semipermeable membrane , chemical engineering , organic chemistry , polymer chemistry , biochemistry , engineering
Following its resolution by diastereomeric complexation, 5,5′,6,6′‐tetrahydroxy‐3,3,3′,3′‐tetramethyl‐1,1′‐spirobisindane (TTSBI) was used to synthesize a chiral ladder polymer, (+)‐ PIM‐CN . (+)‐ PIM‐COOH was also synthesized by the acid hydrolysis of (+)‐ PIM‐CN . Following characterization, both (+)‐ PIM‐CN and (+)‐ PIM‐COOH were solvent cast directly into semipermeable membranes and evaluated for their ability to enable the selective permeation of a range of racemates, including mandelic acid (Man), Fmoc‐phenylalanine, 1,1′‐bi‐2‐naphthol (binol), and TTSBI. High ee values were observed for a number of analytes, and both materials exhibited high permeation rates. A selective diffusion–permeation mechanism was consistent with the results obtained with these materials. Their high permeability, processability, and ease of chemical modification offer considerable potential for liquid‐phase membrane separations and related separation applications.