Design and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applications

Handle URI:
http://hdl.handle.net/10754/625700
Title:
Design and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applications
Authors:
Ma, Xiaohua; Abdulhamid, Mahmoud A.; Pinnau, Ingo ( 0000-0003-3040-9088 )
Abstract:
Two novel carbocyclic pseudo-Tröger’s base-derived dianhydrides, 5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e][8]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][8]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.
KAUST Department:
Advanced Membranes and Porous Materials Research Center; Chemical and Biological Engineering Program; Physical Sciences and Engineering (PSE) Division
Citation:
Ma 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.
Publisher:
American Chemical Society (ACS)
Journal:
Macromolecules
Issue Date:
24-Jul-2017
DOI:
10.1021/acs.macromol.7b01054
Type:
Article
ISSN:
0024-9297; 1520-5835
Sponsors:
This work was supported by funding from King Abdullah University of Science and Technology (KAUST).
Additional Links:
http://pubs.acs.org/doi/full/10.1021/acs.macromol.7b01054
Appears in Collections:
Articles; Advanced Membranes and Porous Materials Research Center; Physical Sciences and Engineering (PSE) Division; Chemical and Biological Engineering Program

Full metadata record

DC FieldValue Language
dc.contributor.authorMa, Xiaohuaen
dc.contributor.authorAbdulhamid, Mahmoud A.en
dc.contributor.authorPinnau, Ingoen
dc.date.accessioned2017-10-03T12:49:34Z-
dc.date.available2017-10-03T12:49:34Z-
dc.date.issued2017-07-24en
dc.identifier.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.en
dc.identifier.issn0024-9297en
dc.identifier.issn1520-5835en
dc.identifier.doi10.1021/acs.macromol.7b01054en
dc.identifier.urihttp://hdl.handle.net/10754/625700-
dc.description.abstractTwo novel carbocyclic pseudo-Tröger’s base-derived dianhydrides, 5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e][8]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][8]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.en
dc.description.sponsorshipThis work was supported by funding from King Abdullah University of Science and Technology (KAUST).en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/full/10.1021/acs.macromol.7b01054en
dc.titleDesign and Synthesis of Polyimides Based on Carbocyclic Pseudo-Tröger’s Base-Derived Dianhydrides for Membrane Gas Separation Applicationsen
dc.typeArticleen
dc.contributor.departmentAdvanced Membranes and Porous Materials Research Centeren
dc.contributor.departmentChemical and Biological Engineering Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalMacromoleculesen
kaust.authorMa, Xiaohuaen
kaust.authorAbdulhamid, Mahmoud A.en
kaust.authorPinnau, Ingoen
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