Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Physical Sciences and Engineering (PSE) Division
Imaging and Characterization Core Lab
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AbstractTwo 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).
CitationMa X, Abdulhamid M, Miao X, Pinnau I (2017) Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes. Macromolecules. Available: http://dx.doi.org/10.1021/acs.macromol.7b02301.
SponsorsThis work was supported by funding from King Abdullah University of Science and Technology (KAUST).
PublisherAmerican Chemical Society (ACS)