Key Features of Polyimide-Derived Carbon Molecular Sieves

Qiu, Wulin; Leisen, Johannes E.; Liu, Zhongyun; Quan, Wenying; Koros, William J.

doi:10.1002/anie.202106740

Title: Key Features of Polyimide-Derived Carbon Molecular Sieves

Journal Article · 03 August 2021 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.202106740 · OSTI ID:1976267

Qiu, Wulin ^[1]; Leisen, Johannes E. ^[2]; Liu, Zhongyun ^[2]; Quan, Wenying ^[2];

^[2]

Georgia Institute of Technology, Atlanta, GA (United States); OSTI
Georgia Institute of Technology, Atlanta, GA (United States)

Carbon molecular sieve (CMS) membranes have impressive separation properties; however, both chemical and morphology structures need to be understood better. Here we characterize CMS with the simplest polyimide (PI) PMDA/pPDA (PMDA=pyromellitic dianhydride, pPDA=p-phenylenediamine), using FTIR, solid-state ¹⁵N-NMR and ¹³C-NMR, XPS, XRD, and Raman spectra to study chemical structure. Here we also compare gas separation properties for this CMS to a CMS derived from a more conventional PI precursor. The detailed characterization shows the presence of aromatic pyridinic, pyrrolic rings as well as graphitic, pyridonic components and a few other groups in both CMS types derived from the very different precursors. The CMS morphologies, while related to precursor and pyrolysis temperature details, show similarities consistent with a physical picture comprising distributed molecular sieving plate-like structures. These results assist in understanding diverse CMS membrane separation performance.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Georgia Institute of Technology, Atlanta, GA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: FG02-04ER15510

OSTI ID:: 1976267

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 41 Vol. 60; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (61)

Ultraselective Carbon Molecular Sieve Membranes with Tailored Synergistic Sorption Selective Properties Zhang, Chen; Koros, William J. Advanced Materials, Vol. 29, Issue 33 https://doi.org/10.1002/adma.201701631	journal	July 2017
Creation of Well‐Defined “Mid‐Sized” Micropores in Carbon Molecular Sieve Membranes Ma, Yao; Jue, Melinda L.; Zhang, Fengyi Angewandte Chemie, Vol. 131, Issue 38 https://doi.org/10.1002/ange.201903105	journal	August 2019
Hyperaging Tuning of a Carbon Molecular‐Sieve Hollow Fiber Membrane with Extraordinary Gas‐Separation Performance and Stability Qiu, Wulin; Vaughn, Justin; Liu, Gongping Angewandte Chemie, Vol. 131, Issue 34 https://doi.org/10.1002/ange.201904913	journal	July 2019
A Self‐Consistent Model for Sorption and Transport in Polyimide‐Derived Carbon Molecular Sieve Gas Separation Membranes Sanyal, Oishi; Hays, Samuel S.; León, Nicholas E. Angewandte Chemie, Vol. 132, Issue 46 https://doi.org/10.1002/ange.202006521	journal	September 2020
Creation of Well‐Defined “Mid‐Sized” Micropores in Carbon Molecular Sieve Membranes Ma, Yao; Jue, Melinda L.; Zhang, Fengyi Angewandte Chemie International Edition, Vol. 58, Issue 38 https://doi.org/10.1002/anie.201903105	journal	September 2019
Hyperaging Tuning of a Carbon Molecular‐Sieve Hollow Fiber Membrane with Extraordinary Gas‐Separation Performance and Stability Qiu, Wulin; Vaughn, Justin; Liu, Gongping Angewandte Chemie International Edition, Vol. 58, Issue 34 https://doi.org/10.1002/anie.201904913	journal	July 2019
A Self‐Consistent Model for Sorption and Transport in Polyimide‐Derived Carbon Molecular Sieve Gas Separation Membranes Sanyal, Oishi; Hays, Samuel S.; León, Nicholas E. Angewandte Chemie International Edition, Vol. 59, Issue 46 https://doi.org/10.1002/anie.202006521	journal	September 2020
Effect of hydrophobic hexafluoroisopropylidene group on the water sorption behaviors of rigid poly(p-phenylene pyromellitimide) polyimide thin films Seo, Jongchul; Yup Lee, Sang; Jang, Wonbong Journal of Applied Polymer Science, Vol. 89, Issue 13 https://doi.org/10.1002/app.12552	journal	July 2003
Structure and surface elemental state analysis of polyimide resin film after carbonization and graphitization Zhao, Shuo; Shi, Zhi-qiang; Wang, Cheng-yang Journal of Applied Polymer Science, Vol. 108, Issue 3 https://doi.org/10.1002/app.27697	journal	January 2008
Gas Separation Performance of Carbon Molecular Sieve Membranes Based on 6FDA-mPDA/DABA (3:2) Polyimide Qiu, Wulin; Zhang, Kuang; Li, Fuyue Stephanie ChemSusChem, Vol. 7, Issue 4 https://doi.org/10.1002/cssc.201300851	journal	February 2014
Carbon Molecular Sieve Membranes Derived from Tröger's Base-Based Microporous Polyimide for Gas Separation Wang, Zhenggong; Ren, Huiting; Zhang, Shenxiang ChemSusChem, Vol. 11, Issue 5 https://doi.org/10.1002/cssc.201702243	journal	February 2018
Isomer‐Tailored Carbon Molecular Sieve Membranes with High Gas Separation Performance Qiu, Wulin; Li, Fuyue Stephanie; Fu, Shilu ChemSusChem, Vol. 13, Issue 19 https://doi.org/10.1002/cssc.202001567	journal	August 2020
Thermal degradation of polymers with phenylene units in the chain. IV. Aromatic polyamides and polyimides Ehlers, G. F. L.; Fisch, K. R.; Powell, W. R. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 8, Issue 12 https://doi.org/10.1002/pol.1970.150081213	journal	December 1970
Magnetic Susceptibility Effects on 13C MAS NMR Spectra of Carbon Materials and Graphite Freitas, Jair C. C.; Emmerich, Francisco G.; Cernicchiaro, Geraldo R. C. Solid State Nuclear Magnetic Resonance, Vol. 20, Issue 1-2 https://doi.org/10.1006/snmr.2001.0030	journal	August 2001
XPS studies by use of the digital difference spectrum technique of functional groups on the surface of carbon fiber Takahagi, T.; Ishitani, A. Carbon, Vol. 22, Issue 1 https://doi.org/10.1016/0008-6223(84)90131-3	journal	January 1984
Carbon molecular sieve films from polyimide Hatori, H.; Yamada, Y.; Shiraishi, M. Carbon, Vol. 30, Issue 2 https://doi.org/10.1016/0008-6223(92)90095-E	journal	January 1992
Evolution of nitrogen functionalities in carbonaceous materials during pyrolysis Pels, J. R.; Kapteijn, F.; Moulijn, J. A. Carbon, Vol. 33, Issue 11, p. 1641-1653 https://doi.org/10.1016/0008-6223(95)00154-6	journal	January 1995
Correlation of separation factor versus permeability for polymeric membranes Robeson, Lloyd M. Journal of Membrane Science, Vol. 62, Issue 2 https://doi.org/10.1016/0376-7388(91)80060-J	journal	October 1991
Investigation of porosity of carbon materials and related effects on gas separation properties Steel, Keisha M.; Koros, William J. Carbon, Vol. 41, Issue 2 https://doi.org/10.1016/S0008-6223(02)00309-3	journal	February 2003
The characterization of activated carbons with oxygen and nitrogen surface groups Biniak, S.; Szymański, G.; Siedlewski, J. Carbon, Vol. 35, Issue 12 https://doi.org/10.1016/S0008-6223(97)00096-1	journal	January 1997
A review on the latest development of carbon membranes for gas separation Ismail, A.; David, L. Journal of Membrane Science, Vol. 193, Issue 1 https://doi.org/10.1016/S0376-7388(01)00510-5	journal	October 2001
Fabrication of carbon membranes for gas separation––a review Saufi, S. M.; Ismail, A. F. Carbon, Vol. 42, Issue 2 https://doi.org/10.1016/j.carbon.2003.10.022	journal	January 2004
Raman microspectroscopy of soot and related carbonaceous materials: Spectral analysis and structural information Sadezky, A.; Muckenhuber, H.; Grothe, H. Carbon, Vol. 43, Issue 8 https://doi.org/10.1016/j.carbon.2005.02.018	journal	July 2005
An investigation of the effects of pyrolysis parameters on gas separation properties of carbon materials Steel, Keisha M.; Koros, William J. Carbon, Vol. 43, Issue 9 https://doi.org/10.1016/j.carbon.2005.02.028	journal	August 2005
XPS and NMR studies of phosphoric acid activated carbons Puziy, A. M.; Poddubnaya, O. I.; Socha, R. P. Carbon, Vol. 46, Issue 15, p. 2113-2123 https://doi.org/10.1016/j.carbon.2008.09.010	journal	December 2008
Effect of polymer precursors on carbon molecular sieve structure and separation performance properties Kiyono, Mayumi; Williams, Paul J.; Koros, William J. Carbon, Vol. 48, Issue 15 https://doi.org/10.1016/j.carbon.2010.08.002	journal	December 2010
Oxygen reduction activity of pyrolyzed polypyrroles studied by 15N solid-state NMR and XPS with principal component analysis Kuroki, Shigeki; Nabae, Yuta; Chokai, Masayuki Carbon, Vol. 50, Issue 1 https://doi.org/10.1016/j.carbon.2011.08.014	journal	January 2012
A solid-state NMR study of the carbonization of polyaniline Kuroki, Shigeki; Hosaka, Yo; Yamauchi, Chiharu Carbon, Vol. 55 https://doi.org/10.1016/j.carbon.2012.12.022	journal	April 2013
Evolution of Raman spectra in nitrogen doped graphene Zafar, Zainab; Ni, Zhen Hua; Wu, Xing Carbon, Vol. 61 https://doi.org/10.1016/j.carbon.2013.04.065	journal	September 2013
Aromatic polyimides as carbon precursors Inagaki, Michio; Ohta, Naoto; Hishiyama, Yoshihiro Carbon, Vol. 61 https://doi.org/10.1016/j.carbon.2013.05.035	journal	September 2013
Nanoscale characterization of aircraft soot: A high-resolution transmission electron microscopy, Raman spectroscopy, X-ray photoelectron and near-edge X-ray absorption spectroscopy study Parent, P.; Laffon, C.; Marhaba, I. Carbon, Vol. 101 https://doi.org/10.1016/j.carbon.2016.01.040	journal	May 2016
Amorphous, turbostratic and crystalline carbon membranes with hydrogen selectivity Wollbrink, A.; Volgmann, K.; Koch, J. Carbon, Vol. 106 https://doi.org/10.1016/j.carbon.2016.04.062	journal	September 2016
Carbon molecular sieve structure development and membrane performance relationships Rungta, Meha; Wenz, Graham B.; Zhang, Chen Carbon, Vol. 115 https://doi.org/10.1016/j.carbon.2017.01.015	journal	May 2017
New insights into structural evolution in carbon molecular sieve membranes during pyrolysis Adams, Jason S.; Itta, Arun K.; Zhang, Chen Carbon, Vol. 141 https://doi.org/10.1016/j.carbon.2018.09.039	journal	January 2019
Envisioned role of slit bypass pores in physical aging of carbon molecular sieve membranes Hays, Samuel S.; Sanyal, Oishi; León, Nicholas E. Carbon, Vol. 157 https://doi.org/10.1016/j.carbon.2019.10.036	journal	February 2020
XPS study of reductively and non-reductively modified coals Kozłowski, Mieczysław Fuel, Vol. 83, Issue 3 https://doi.org/10.1016/j.fuel.2003.08.004	journal	February 2004
XPS study and physico-chemical properties of nitrogen-enriched microporous activated carbon from high volatile bituminous coal Pietrzak, Robert Fuel, Vol. 88, Issue 10 https://doi.org/10.1016/j.fuel.2009.04.017	journal	October 2009
An XPS study for mechanisms of arsenate adsorption onto a magnetite-doped activated carbon fiber Zhang, Shujuan; Li, Xiao-yan; Chen, J. Paul Journal of Colloid and Interface Science, Vol. 343, Issue 1 https://doi.org/10.1016/j.jcis.2009.11.001	journal	March 2010
Self-assembly of mildly reduced graphene oxide monolayer for enhanced Raman scattering Yin, Fenping; Wu, Shang; Wang, Yanbin Journal of Solid State Chemistry, Vol. 237 https://doi.org/10.1016/j.jssc.2016.01.015	journal	May 2016
Effects of phenolic resin pyrolysis conditions on carbon membrane performance for gas separation Centeno, T. A.; Vilas, J. L.; Fuertes, A. B. Journal of Membrane Science, Vol. 228, Issue 1 https://doi.org/10.1016/j.memsci.2003.09.010	journal	January 2004
The upper bound revisited Robeson, Lloyd M. Journal of Membrane Science, Vol. 320, Issue 1-2, p. 390-400 https://doi.org/10.1016/j.memsci.2008.04.030	journal	July 2008
Olefins-selective asymmetric carbon molecular sieve hollow fiber membranes for hybrid membrane-distillation processes for olefin/paraffin separations Xu, Liren; Rungta, Meha; Brayden, Mark K. Journal of Membrane Science, Vol. 423-424 https://doi.org/10.1016/j.memsci.2012.08.028	journal	December 2012
High pressure pure- and mixed-gas separation of CO2/CH4 by thermally-rearranged and carbon molecular sieve membranes derived from a polyimide of intrinsic microporosity Swaidan, Raja; Ma, Xiaohua; Litwiller, Eric Journal of Membrane Science, Vol. 447 https://doi.org/10.1016/j.memsci.2013.07.057	journal	November 2013
Post-combustion carbon dioxide capture via 6FDA/BPDA-DAM hollow fiber membranes at sub-ambient temperatures Liu, Lu; Qiu, Wulin; Sanders, Edgar S. Journal of Membrane Science, Vol. 510 https://doi.org/10.1016/j.memsci.2016.03.027	journal	July 2016
Spirobisindane-based polyimide as efficient precursor of thermally-rearranged and carbon molecular sieve membranes for enhanced propylene/propane separation Swaidan, Ramy J.; Ma, Xiaohua; Pinnau, Ingo Journal of Membrane Science, Vol. 520 https://doi.org/10.1016/j.memsci.2016.08.057	journal	December 2016
Energy-efficient polymeric gas separation membranes for a sustainable future: A review Sanders, David F.; Smith, Zachary P.; Guo, Ruilan Polymer, Vol. 54, Issue 18 https://doi.org/10.1016/j.polymer.2013.05.075	journal	August 2013
Multilevel structure analysis of polyimide fibers with different chemical constitutions Lei, Huanyu; Zhang, Mengying; Niu, Hongqing Polymer, Vol. 149 https://doi.org/10.1016/j.polymer.2018.06.067	journal	August 2018
Review on Recent Progress in Nitrogen-Doped Graphene: Synthesis, Characterization, and Its Potential Applications Wang, Haibo; Maiyalagan, Thandavarayan; Wang, Xin ACS Catalysis, Vol. 2, Issue 5 https://doi.org/10.1021/cs200652y	journal	April 2012
Evaluation of Raman Parameters Using Visible Raman Microscopy for Soot Oxidative Reactivity Seong, Hee Je; Boehman, André L. Energy & Fuels, Vol. 27, Issue 3 https://doi.org/10.1021/ef301520y	journal	March 2013
High Pressure CO ₂ /CH ₄ Separation Using Carbon Molecular Sieve Hollow Fiber Membranes Vu, De Q.; Koros, William J.; Miller, Stephen J. Industrial & Engineering Chemistry Research, Vol. 41, Issue 3 https://doi.org/10.1021/ie010119w	journal	February 2002
Separation of Ethane/Ethylene and Propane/Propylene Systems with a Carbonized BPDA−pp‘ODA Polyimide Membrane Hayashi, Jun-ichiro; Mizuta, Hirotaka; Yamamoto, Masatake Industrial & Engineering Chemistry Research, Vol. 35, Issue 11 https://doi.org/10.1021/ie960264n	journal	January 1996
Surface Sensitive Study To Determine the Reactivity of Soot with the Focus on the European Emission Standards IV and VI Schuster, Manfred E.; Hävecker, Michael; Arrigo, Rosa The Journal of Physical Chemistry A, Vol. 115, Issue 12 https://doi.org/10.1021/jp1088417	journal	March 2011
Basis of Permeability/Selectivity Tradeoff Relations in Polymeric Gas Separation Membranes Freeman, Benny D. Macromolecules, Vol. 32, Issue 2 https://doi.org/10.1021/ma9814548	journal	January 1999
Correlation of C1s chemical state intensities with the O1s intensity in the XPS analysis of anodically oxidized glass-like carbon samples Yumitori, Shuji Journal of Materials Science, Vol. 35, Issue 1, p. 139-146 https://doi.org/10.1023/A:1004761103919	journal	January 2000
Materials for next-generation molecularly selective synthetic membranes Koros, William J.; Zhang, Chen Nature Materials, Vol. 16, Issue 3 https://doi.org/10.1038/nmat4805	journal	January 2017
XPS studies on dispersed and immobilised carbon nitrides used for dye degradation Rieß, Julian; Lublow, Michael; Anders, Steven Photochemical & Photobiological Sciences, Vol. 18, Issue 7 https://doi.org/10.1039/C9PP00144A	journal	January 2019
Dynamic surface rearrangement and thermal stability of nitrogen functional groups on carbon nanotubes Arrigo, Rosa; Hävecker, Michael; Schlögl, Robert Chemical Communications, Issue 40 https://doi.org/10.1039/b812769g	journal	January 2008
Study of molecular sieve carbons. Part 1.—Pore structure, gradual pore opening and mechanism of molecular sieving Koresh, Jacob; Soffer, Abraham Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 76, Issue 0 https://doi.org/10.1039/f19807602457	journal	January 1980
Interpretation of Raman spectra of disordered and amorphous carbon Ferrari, A. C.; Robertson, J. Physical Review B, Vol. 61, Issue 20, p. 14095-14107 https://doi.org/10.1103/PhysRevB.61.14095	journal	May 2000
Oxygen Reduction Activity of Pyrolyzed Polyanilines Studied by XPS and ¹⁵ N Solid-State NMR with Principal Component Analysis Kuroki, Shigeki; Hosaka, Yo; Yamauchi, Chiharu Journal of The Electrochemical Society, Vol. 159, Issue 7 https://doi.org/10.1149/2.079207jes	journal	January 2012
Nitrogen Doped Ordered Mesoporous Carbon as Support of PtRu Nanoparticles for Methanol Electro-Oxidation Sebastián, David; Nieto-Monge, María; Pérez-Rodríguez, Sara Energies, Vol. 11, Issue 4 https://doi.org/10.3390/en11040831	journal	April 2018

Similar Records

Key Features of Polyimide‐Derived Carbon Molecular Sieves

Journal Article · 2021 · Angewandte Chemie · OSTI ID:1818781

Qiu, Wulin; Leisen, Johannes E.; Liu, Zhongyun; +2 more

Synergistic Tuning of Microstructure and Morphology in Carbon Molecular Sieve Hollow Fibers for Propylene/Propane Separation

Journal Article · 2024 · Angewandte Chemie (International Edition) · OSTI ID:2475859

Liu, Zhongyun; Cao, Yuhe; Koros, William J.

Synergistic Tuning of Microstructure and Morphology in Carbon Molecular Sieve Hollow Fibers for Propylene/Propane Separation

Journal Article · 2025 · Angewandte Chemie · OSTI ID:2475884

Liu, Zhongyun; Cao, Yuhe; Koros, William J.

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
carbon molecular sieve
membrane
polyimide
separation
structure

Title: Key Features of Polyimide-Derived Carbon Molecular Sieves

Citation Formats

References (61)

Similar Records

Related Subjects