Molecular design of Tröger's base-based polymers with intrinsic microporosity for gas separation

Youchang Xiao, Liling Zhang, Li Xu, Tai-Shung Chung*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

High performance polymers with intrinsic microporosity have been prepared via introducing sites of contortion and chain stiffness with the incorporation of Tröger's base (TB). An experimental investigation coupling with computational simulation was executed to study the effects of polymers’ chemical structures on their gas separation performance. A general acid-catalyzed and low-temperature synthetic route was adopted to achieve the polymerization between 1, 5-diaminonaphathelen (1,5-DAN) and 4,4′-(Hexafluoroisopropylidene) dianiline (4,4′-HFD) via condensation and cyclization. It is found that the resultant 1, 5-diaminonaphathelen Tröger's base-based polymer (1,5-DTBP), 4,4′-(Hexafluoroisopropylidene) dianiline Tröger's base-based polymer (4,4′-HTBP) and their copolymers are readily soluble in the N-methyl-2-pyrrolidone (NMP) solvent, cast as free standing films and exhibit good gas separation performance. The TB-based polymer containing 10% 4,4′-HFD has both the highest permeability and acceptable selectivity even exceeding the Robeson upper bound for H2/CH4. Molecularly designed ineffective chain packing via the enhancement of backbone rigidity and introduction of bulky side groups is proved to be the main mechanism that achieves the high separation performance. Since the newly synthesized TB-based polymers display desirable H2/CH4 and H2/N2 gas separation performance approaching the Robeson upper bounds, this work proves the feasibility of designing advanced polymeric materials with Tröger's base as the sole constituent.

Original languageEnglish (US)
Pages (from-to)65-72
Number of pages8
JournalJournal of Membrane Science
Volume521
DOIs
StatePublished - Jan 1 2017

Keywords

  • Gas separation
  • Polymeric membrane
  • Polymers with intrinsic microporosity
  • Tröger's base

ASJC Scopus subject areas

  • Biochemistry
  • Materials Science(all)
  • Physical and Theoretical Chemistry
  • Filtration and Separation

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