Chiral Polymers of Intrinsic Microporosity: Selective Membrane Permeation of Enantiomers |
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| Authors: | Xilun Weng Dr José E Baez Dr Mariya Khiterer Madelene Y Hoe Dr Zongbi Bao Dr Kenneth J Shea |
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| Institution: | 1. Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA);2. Key Laboratory of Biomass Chemical Engineering of the Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027 (China) |
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| Abstract: | 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. |
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| Keywords: | chirality enantioselectivity membranes permeation polymers of intrinsic microporosity |
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