Chiral polymers of intrinsic microporosity: selective membrane permeation of enantiomers

Xilun Weng; José E Baez; Mariya Khiterer; Madelene Y Hoe; Zongbi Bao; Kenneth J Shea

doi:10.1002/anie.201504934

Chiral polymers of intrinsic microporosity: selective membrane permeation of enantiomers

Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11214-8. doi: 10.1002/anie.201504934.

Authors

Xilun Weng^{1

2}, José E Baez¹, Mariya Khiterer¹, Madelene Y Hoe¹, Zongbi Bao², Kenneth J Shea³

Affiliations

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).
³ Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA). kjshea@uci.edu.

PMID: 26352031
DOI: 10.1002/anie.201504934

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.

Keywords: chirality; enantioselectivity; membranes; permeation; polymers of intrinsic microporosity.