Chiral polymers of intrinsic microporosity: selective membrane permeation of enantiomers.
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.
Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).|Key Laboratory of Biomass Chemical Engineering of the Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027 (China).
Xilun
X
Weng
Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).
José E
JE
Baez
Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).
Mariya
M
Khiterer
Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).
Madelene Y
MY
Hoe
Key Laboratory of Biomass Chemical Engineering of the Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027 (China).
Zongbi
Z
Bao
Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA). kjshea@uci.edu.
Kenneth J
KJ
Shea
chirality; enantioselectivity; membranes; permeation; polymers of intrinsic microporosity