Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation
AuthorsAbdulhamid, Mahmoud A.
Lai, Holden W. H.
Teo, Yew Chin
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Engineering Program
Physical Science and Engineering (PSE) Division
KAUST Grant NumberBAS/1/1323-01-01
Online Publication Date2019-02-06
Print Publication Date2019-03-12
Permanent link to this recordhttp://hdl.handle.net/10754/631113
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AbstractWe synthesized a series of rigid ladder-type diamines from readily available bromoanilines and norbornadiene in one step using facile catalytic arene-norbornene annulation (CANAL). Polycondensation of CANAL ladder diamines with 4,4’-(hexafluoroisopropylidene) diphthalic anhydride led to a series of microporous polyimides with different degrees of rotational freedom around the imide linkages. These CANAL-PIs exhibited good solubility in a wide range of organic solvents, high thermal stability with decomposition temperature above 450 °C, high Brunauer-Emmett-Teller sur-face areas of ~ 200 – 530 m2 g-1, and abundant micropore volume with variable pore size distributions. Mechanically robust membranes can be easily formed from these CANAL-PIs and gave high gas permeabilities and moderate gas-pair selectivities. CANAL-PIs had higher permeability and similar permselectivity compared to analogous PIs synthe-sized from Tröger’s base and carbocyclic Tröger’s base diamines under identical test conditions. CANAL-PIs also exhibited relatively slow physical aging. These favorable properties and performance make microporous polymers based on CANAL ladder motifs promising membrane materials for important gas separation.
CitationAbdulhamid MA, Lai HWH, Wang Y, Jin Z, Teo YC, et al. (2019) Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation. Chemistry of Materials. Available: http://dx.doi.org/10.1021/acs.chemmater.8b05359.
SponsorsWe thank U.S. Army Research Office (W911NF-16-1-0018 to Y. Xia), the Donors of the American Chemical Society Petroleum Research Fund (56820-DN17 to Y. Xia), the Semiconductor Research Corporation, seed funding from the Stanford Natural Gas Initiative, and the King Abdullah University of Science and Technology (BAS/1/1323-01-01 to I. Pinnau) for supporting of this research. Single-crystal X-ray diffraction experiments were performed at beamline 11.3.1 at the Advanced Light Source (ALS). The ALS is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under contract no. DE-AC02-05CH11231. H. W. H. Lai thanks the National Science Foundation for the Graduate Research Fellowship (DGE- 156518) and the Stanford Office of the Provost for Graduate Education for the EDGE-STEM fellowship. Y. C. Teo was supported by an A*STAR graduate fellowship.
PublisherAmerican Chemical Society (ACS)
JournalChemistry of Materials
RelationsIs Supplemented By:
Abdulhamid, M. A., Lai, H. W. H., Wang, Y., Jin, Z., Teo, Y. C., Ma, X., Pinnau, I., & Xia, Y. (2019). CCDC 1848638: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC201NH7. DOI: 10.5517/ccdc.csd.cc201nh7 Handle: 10754/664441