Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

Mahmoud A. Abdulhamid, Holden W. H. Lai, Yingge Wang, Zexin Jin, Yew Chin Teo, Xiaohua Ma, Ingo Pinnau, Yan Xia

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

We synthesized a series of rigid ladder-type diamines from readily available bromoanilines and norbornadiene in one step using facile catalytic arene-norbornene annulation (CANAL). Polycondensation of CANAL ladder diamines with 4,4’-(hexafluoroisopropylidene) diphthalic anhydride led to a series of microporous polyimides with different degrees of rotational freedom around the imide linkages. These CANAL-PIs exhibited good solubility in a wide range of organic solvents, high thermal stability with decomposition temperature above 450 °C, high Brunauer-Emmett-Teller sur-face areas of ~ 200 – 530 m2 g-1, and abundant micropore volume with variable pore size distributions. Mechanically robust membranes can be easily formed from these CANAL-PIs and gave high gas permeabilities and moderate gas-pair selectivities. CANAL-PIs had higher permeability and similar permselectivity compared to analogous PIs synthe-sized from Tröger’s base and carbocyclic Tröger’s base diamines under identical test conditions. CANAL-PIs also exhibited relatively slow physical aging. These favorable properties and performance make microporous polymers based on CANAL ladder motifs promising membrane materials for important gas separation.
Original languageEnglish (US)
Pages (from-to)1767-1774
Number of pages8
JournalChemistry of Materials
Volume31
Issue number5
DOIs
StatePublished - Feb 6 2019

Fingerprint Dive into the research topics of 'Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation'. Together they form a unique fingerprint.

Cite this