Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes

Handle URI:
http://hdl.handle.net/10754/626295
Title:
Facile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranes
Authors:
Ma, Xiaohua; Abdul Hamid, Mahmoud; Miao, Xiaohe; Pinnau, Ingo ( 0000-0003-3040-9088 )
Abstract:
Two 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).
KAUST Department:
Advanced Membranes and Porous Materials Research Center; Physical Sciences and Engineering (PSE) Division; Imaging and Characterization Core Lab
Citation:
Ma 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.
Publisher:
American Chemical Society (ACS)
Journal:
Macromolecules
Issue Date:
4-Dec-2017
DOI:
10.1021/acs.macromol.7b02301
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.7b02301
Appears in Collections:
Articles; Advanced Membranes and Porous Materials Research Center; Advanced Nanofabrication, Imaging and Characterization Core Lab; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorMa, Xiaohuaen
dc.contributor.authorAbdul Hamid, Mahmouden
dc.contributor.authorMiao, Xiaoheen
dc.contributor.authorPinnau, Ingoen
dc.date.accessioned2017-12-05T13:15:50Z-
dc.date.available2017-12-05T13:15:50Z-
dc.date.issued2017-12-04en
dc.identifier.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.en
dc.identifier.issn0024-9297en
dc.identifier.issn1520-5835en
dc.identifier.doi10.1021/acs.macromol.7b02301en
dc.identifier.urihttp://hdl.handle.net/10754/626295-
dc.description.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).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.7b02301en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Macromolecules, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/full/10.1021/acs.macromol.7b02301.en
dc.titleFacile Synthesis of a Hydroxyl-Functionalized Tröger’s Base Diamine: A New Building Block for High-Performance Polyimide Gas Separation Membranesen
dc.typeArticleen
dc.contributor.departmentAdvanced Membranes and Porous Materials Research Centeren
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentImaging and Characterization Core Laben
dc.identifier.journalMacromoleculesen
dc.eprint.versionPost-printen
kaust.authorMa, Xiaohuaen
kaust.authorAbdul Hamid, Mahmouden
kaust.authorMiao, Xiaoheen
kaust.authorPinnau, Ingoen
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