Design and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applications
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Chemical and Biological Engineering Program
Physical Sciences and Engineering (PSE) Division
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AbstractTwo novel carbocyclic pseudo-Tröger’s base-derived dianhydrides, 5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e]annulene-2,3,8,9-tetracarboxylic anhydride (CTB1) and its dione-substituted analogue 6,12-dioxo-5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e]annulene-2,3,8,9-tetracarboxylic dianhydride (CTB2), were made and used for the synthesis of soluble polyimides of intrinsic microporosity with 3,3′-dimethylnaphthidine (DMN). The polyimides CTB1-DMN and CTB2-DMN exhibited excellent thermal stability of ∼500 °C and high BET surface areas of 580 and 469 m2 g–1, respectively. A freshly made dione-substituted CTB2-DMN membrane demonstrated promising gas separation performance with O2 permeability of 206 barrer and O2/N2 selectivity of 5.2. A higher O2 permeability of 320 barrer and lower O2/N2 selectivity of 4.2 were observed for a fresh CTB1-DMN film due to its higher surface area and less tightly packed structure as indicated by weaker charge-transfer complex interactions. Physical aging over 60 days resulted in reduction in gas permeability and moderately enhanced selectivity. CTB2-DMN exhibited notable performance with gas permeation data located between the 2008 and 2015 permeability/selectivity upper bounds for O2/N2 and H2/CH4.
CitationMa X, Abdulhamid MA, Pinnau I (2017) Design and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applications. Macromolecules 50: 5850–5857. Available: http://dx.doi.org/10.1021/acs.macromol.7b01054.
SponsorsThis work was supported by funding from King Abdullah University of Science and Technology (KAUST).
PublisherAmerican Chemical Society (ACS)