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
Permanent link to this recordhttp://hdl.handle.net/10754/625700
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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)