Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 38, Pages 11214-11218Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504934
Keywords
chirality; enantioselectivity; membranes; permeation; polymers of intrinsic microporosity
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Funding
- National Science Foundation [CHE-1153118]
- China Scholarship Council
- Direct For Mathematical & Physical Scien [1153118] Funding Source: National Science Foundation
- Division Of Chemistry [1153118] Funding Source: National Science Foundation
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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), Fmocphenylalanine, 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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