Facile Synthesis of a Hydroxyl-Functionalized Tröger's Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes

Xiaohua Ma, Mahmoud Abdulhamid, Xiaohe Miao, Ingo Pinnau*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

Abstract

Two intrinsically microporous polyimides (PIM-PIs) were synthesized by the polycondensation reaction of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) and 3,3,3′,3′-tetramethylspirobisindane-6,7,6′,7′-tetracarboxylic dianhydride (SBI) with a newly designed o-hydroxyl-functionalized Tröger's base diamine, 1,7-diamino-6H,12H-5,11-methanodibenzo[1,5]diazocine-2,8-diol (HTB). Both amorphous PIM-PIs were soluble in aprotic solvents and showed excellent thermal stability with onset decomposition temperature of ∼380 °C. SBI-HTB displayed a higher CO2 permeability (466 vs 67 barrer) than 6FDA-HTB but a significantly lower selectivity for CO2/CH4 (29 vs 73), H2/CH4 (29 vs 181), O2/N2 (4.6 vs 6.0), and N2/CH4 (1 vs 2.5). 6FDA-HTB displayed the highest gas-pair permselectivity values of all reported OH-functionalized PIM-PIs to date. The high permselectivity of 6FDA-HTB resulted primarily from exceptional diffusion selectivity due to strong size-sieving properties caused by hydrogen bonding between the proton of the hydroxyl group and the nitrogen atoms in the tertiary amine of the Tröger's base (O-H···N).

Original languageEnglish (US)
Pages (from-to)9569-9576
Number of pages8
JournalMacromolecules
Volume50
Issue number24
DOIs
StatePublished - Dec 26 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Organic Chemistry

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