Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

Mahmoud A. Abdulhamid; Holden W. H. Lai; Yingge Wang; Zexin Jin; Yew Chin Teo; Xiaohua Ma; Ingo Pinnau; Yan Xia

doi:10.1021/acs.chemmater.8b05359

Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

Mahmoud A. Abdulhamid, Holden W. H. Lai, Yingge Wang, Zexin Jin, Yew Chin Teo, Xiaohua Ma, Ingo Pinnau, Yan Xia

Research output: Contribution to journal › Article › peer-review

66 Scopus citations

Abstract

We 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.

Original language	English (US)
Pages (from-to)	1767-1774
Number of pages	8
Journal	Chemistry of Materials
Volume	31
Issue number	5
DOIs	https://doi.org/10.1021/acs.chemmater.8b05359
State	Published - Feb 6 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): BAS/1/1323-01-01
Acknowledgements: We 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.

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10.1021/acs.chemmater.8b05359

https://repository.kaust.edu.sa/bitstream/10754/631113/1/acs.chemmater.8b05359.pdf

Cite this

@article{a37c7e46e7c5435088e383cea1c0358d,

title = "Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation",

abstract = "We 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{\textquoteright}-(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 Tr{\"o}ger{\textquoteright}s base and carbocyclic Tr{\"o}ger{\textquoteright}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.",

author = "Abdulhamid, {Mahmoud A.} and Lai, {Holden W. H.} and Yingge Wang and Zexin Jin and Teo, {Yew Chin} and Xiaohua Ma and Ingo Pinnau and Yan Xia",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): BAS/1/1323-01-01 Acknowledgements: We 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.",

year = "2019",

month = feb,

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doi = "10.1021/acs.chemmater.8b05359",

language = "English (US)",

volume = "31",

pages = "1767--1774",

journal = "Chemistry of Materials",

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T1 - Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

AU - Abdulhamid, Mahmoud A.

AU - Lai, Holden W. H.

AU - Wang, Yingge

AU - Jin, Zexin

AU - Teo, Yew Chin

AU - Ma, Xiaohua

AU - Pinnau, Ingo

AU - Xia, Yan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): BAS/1/1323-01-01 Acknowledgements: We 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.

PY - 2019/2/6

Y1 - 2019/2/6

N2 - We 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.

AB - We 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.

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U2 - 10.1021/acs.chemmater.8b05359

DO - 10.1021/acs.chemmater.8b05359

M3 - Article

SN - 0897-4756

VL - 31

SP - 1767

EP - 1774

JO - Chemistry of Materials

JF - Chemistry of Materials

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ER -

Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

Abstract

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CCDC 1848638: Experimental Crystal Structure Determination : 4,7,13,16-tetramethylhexacyclo[8.8.1.02,9.03,8.011,18.012,17]nonadeca-3,5,7,12,14,16-hexaene

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Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation

Abstract

Bibliographical note

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CCDC 1848638: Experimental Crystal Structure Determination : 4,7,13,16-tetramethylhexacyclo[8.8.1.02,9.03,8.011,18.012,17]nonadeca-3,5,7,12,14,16-hexaene

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