Analysis of governing factors controlling gas transport through fresh and aged triptycene-based polyimide films

Weidman, Jennifer R.; Luo, Shuangjiang; Doherty, Cara M.; Hill, Anita J.; Gao, Peiyuan; Guo, Ruilan

doi:10.1016/j.memsci.2016.09.013

Analysis of governing factors controlling gas transport through fresh and aged triptycene-based polyimide films

Journal Article · Sat Sep 10 00:00:00 EDT 2016 · Journal of Membrane Science

DOI:https://doi.org/10.1016/j.memsci.2016.09.013· OSTI ID:1534095

Weidman, Jennifer R. ^[1]; Luo, Shuangjiang ^[2]; Doherty, Cara M. ^[3]; Hill, Anita J. ^[3]; Gao, Peiyuan ^[4]; Guo, Ruilan ^[2]

University of Notre Dame, IN (United States); DOE/OSTI
University of Notre Dame, IN (United States)
Commonwealth Scientific and Industrial Research Organization (CSIRO), Victoria (Australia)
Chinese Academy of Sciences (CAS), Beijing (China)

In this report the fundamental gas transport properties and physical aging behavior of a series of triptycene-based polyimides with various substitution groups were investigated. Wide-angle x-ray diffraction revealed that the 6FDA-1,4-triptycene polyimides exhibit two chain packing domains with d-spacing values of ~6.7 Å and ~5.3 Å, corresponding to triptycene-induced chain packing disruption and chain segments lacking the triptycene moiety, respectively. Positron annihilation lifetime spectroscopy (PALS) showed a bimodal distribution of microcavity size made up of triptycene cleft cavities that are ~3 Å diameter and larger interchain cavities with an average diameter of ~7 Å. Additionally, PALS confirmed 6FDA-1,4-trip_CH₃ has the lowest fractional free volume, primarily due to smaller contributions from the interchain cavities, and 6FDA-1,4-trip_CF₃ has the largest fractional free volume. It was also found that the addition of substituent groups had a unique and positive effect on the aging properties over nine months, in which the addition of CH₃ and CF₃ groups led to permeability increases of ~20% and ~40%, respectively. This is caused by the combination of the lowered driving force for physical aging, the substituent groups sterically hindering tighter packing with time, and the interconnectivity and/or unblocking of free volume over time through small-scale, local chain motion.

View Accepted Manuscript (DOE)

Research Organization:: University of Notre Dame, IN (United States)

Sponsoring Organization:: ACS Petroleum Research Fund; Australian Research Council; USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: SC0010330

OSTI ID:: 1534095

Alternate ID(s):: OSTI ID: 1397957

Journal Information:: Journal of Membrane Science, Journal Name: Journal of Membrane Science Journal Issue: C Vol. 522; ISSN 0376-7388

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Triptycene Induced Enhancement of Membrane Gas Selectivity for Microporous Tröger's Base Polymers Carta, Mariolino; Croad, Matthew; Malpass-Evans, Richard Advanced Materials, Vol. 26, Issue 21 https://doi.org/10.1002/adma.201305783	journal	March 2014
UV-Rearranged PIM-1 Polymeric Membranes for Advanced Hydrogen Purification and Production Li, Fu Yun; Xiao, Youchang; Ong, Yee Kang Advanced Energy Materials, Vol. 2, Issue 12 https://doi.org/10.1002/aenm.201200296	journal	July 2012
Ending Aging in Super Glassy Polymer Membranes Lau, Cher Hon; Nguyen, Phuc Tien; Hill, Matthew R. Angewandte Chemie International Edition, Vol. 53, Issue 21 https://doi.org/10.1002/anie.201402234	journal	April 2014
Matrimid polyimide membranes for the separation of carbon dioxide from methane Sridhar, S.; Veerapur, R. S.; Patil, M. B. Journal of Applied Polymer Science, Vol. 106, Issue 3 https://doi.org/10.1002/app.26306	journal	January 2007
Polymers of Intrinsic Microporosity (PIMs): Bridging the Void between Microporous and Polymeric Materials McKeown, Neil B.; Budd, Peter M.; Msayib, Kadhum J. Chemistry - A European Journal, Vol. 11, Issue 9, p. 2610-2620 https://doi.org/10.1002/chem.200400860	journal	April 2005
High Performance Polyimide with High Internal Free Volume Elements Cho, Yoon Jin; Park, Ho Bum Macromolecular Rapid Communications, Vol. 32, Issue 7 https://doi.org/10.1002/marc.201000690	journal	January 2011
Physical aging in plastics and other glassy materials Strum, L. C. E. Polymer Engineering and Science, Vol. 17, Issue 3 https://doi.org/10.1002/pen.760170305	journal	March 1977
Triptycene polymers Hoffmeister, E.; Kropp, J. E.; McDowell, T. L. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 7, Issue 1 https://doi.org/10.1002/pol.1969.150070107	journal	January 1969
Sorption of carbon dioxide in fluorinated poyimides Tanaka, Kazuhiro; Kita, Hidetoshi; Okamoto, Ken‐Ichi Journal of Polymer Science Part B: Polymer Physics, Vol. 31, Issue 9 https://doi.org/10.1002/polb.1993.090310908	journal	August 1993
Correlations between gas permeation and free-volume hole properties probed by positron annihilation spectroscopy Jean, Y. C.; Yuan, J. -P.; Liu, J. Journal of Polymer Science Part B: Polymer Physics, Vol. 33, Issue 17 https://doi.org/10.1002/polb.1995.090331708	journal	December 1995
Order in amorphous di‐n‐alkyl itaconate polymers, copolymers, and blends Arrighi, V.; Holmes, P. F.; McEwen, I. J. Journal of Polymer Science Part B: Polymer Physics, Vol. 42, Issue 21 https://doi.org/10.1002/polb.20265	journal	September 2004
The temperature dependence of positron lifetimes in solid pivalic acid Eldrup, M.; Lightbody, D.; Sherwood, J. N. Chemical Physics, Vol. 63, Issue 1-2 https://doi.org/10.1016/0301-0104(81)80307-2	journal	December 1981
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
Positron annihilation—A probe for nanoscale voids and free volume? Pethrick, Richard A. Progress in Polymer Science, Vol. 22, Issue 1 https://doi.org/10.1016/S0079-6700(96)00023-8	journal	January 1997
Correlation and prediction of gas permeability in glassy polymer membrane materials via a modified free volume based group contribution method Park, J. Y.; Paul, D. R. Journal of Membrane Science, Vol. 125, Issue 1 https://doi.org/10.1016/S0376-7388(96)00061-0	journal	March 1997
Gas separation membranes from polymers of intrinsic microporosity Budd, P.; Msayib, K.; Tattershall, C. Journal of Membrane Science, Vol. 251, Issue 1-2 https://doi.org/10.1016/j.memsci.2005.01.009	journal	April 2005
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
Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: Polybenzodioxane PIM-1 Budd, P.; Mckeown, N.; Ghanem, B. Journal of Membrane Science, Vol. 325, Issue 2 https://doi.org/10.1016/j.memsci.2008.09.010	journal	December 2008
Constructing CO2 transport passageways in Matrimid® membranes using nanohydrogels for efficient carbon capture Li, Xueqin; Wang, Meidi; Wang, Shaofei Journal of Membrane Science, Vol. 474 https://doi.org/10.1016/j.memsci.2014.10.003	journal	January 2015
Molecular origins of fast and selective gas transport in pentiptycene-containing polyimide membranes and their physical aging behavior Luo, Shuangjiang; Wiegand, Jennifer R.; Gao, Peiyuan Journal of Membrane Science, Vol. 518 https://doi.org/10.1016/j.memsci.2016.06.034	journal	November 2016
Advanced fitting algorithms for analysing positron annihilation lifetime spectra Pascual-Izarra, Carlos; Dong, Aurelia W.; Pas, Steven J. Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment, Vol. 603, Issue 3 https://doi.org/10.1016/j.nima.2009.01.205	journal	May 2009
Physical aging of ultrathin glassy polymer films tracked by gas permeability Rowe, Brandon W.; Freeman, Benny D.; Paul, Donald R. Polymer, Vol. 50, Issue 23 https://doi.org/10.1016/j.polymer.2009.09.037	journal	November 2009
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
Gas permeation in thin films of “high free-volume” glassy perfluoropolymers: Part I. Physical aging Tiwari, Rajkiran R.; Smith, Zachary P.; Lin, Haiqing Polymer, Vol. 55, Issue 22 https://doi.org/10.1016/j.polymer.2014.09.022	journal	October 2014
Miscible blends of carboxylated polymers of intrinsic microporosity (cPIM-1) and Matrimid Yong, Wai Fen; Chung, Tai-Shung Polymer, Vol. 59 https://doi.org/10.1016/j.polymer.2015.01.013	journal	February 2015
Suppression of aging and plasticization in highly permeable polymers Yong, Wai Fen; Kwek, Kar Hui Andrel; Liao, Kuo-Sung Polymer, Vol. 77 https://doi.org/10.1016/j.polymer.2015.09.075	journal	October 2015
Physical Aging, Plasticization and Their Effects on Gas Permeation in “Rigid” Polymers of Intrinsic Microporosity Swaidan, Raja; Ghanem, Bader; Litwiller, Eric Macromolecules, Vol. 48, Issue 18 https://doi.org/10.1021/acs.macromol.5b01581	journal	August 2015
Iptycenes in the Design of High Performance Polymers Swager, Timothy M. Accounts of Chemical Research, Vol. 41, Issue 9 https://doi.org/10.1021/ar800107v	journal	September 2008
Solid-State Structures of Phenyleneethynylenes: Comparison of Monomers and Polymers Bunz, Uwe H. F.; Enkelmann, Volker; Kloppenburg, Lioba Chemistry of Materials, Vol. 11, Issue 6 https://doi.org/10.1021/cm990036u	journal	April 1999
Membrane Gas Separation: A Review/State of the Art Bernardo, P.; Drioli, E.; Golemme, G. Industrial & Engineering Chemistry Research, Vol. 48, Issue 10 https://doi.org/10.1021/ie8019032	journal	May 2009
van der Waals Volumes and Radii Bondi, A. The Journal of Physical Chemistry, Vol. 68, Issue 3, p. 441-451 https://doi.org/10.1021/j100785a001	journal	March 1964
Tritriptycene: a D3h C62 hydrocarbon with three U-shaped cavities Bashir-Hashemi, Abdollah.; Hart, Harold.; Ward, Donald L. Journal of the American Chemical Society, Vol. 108, Issue 21 https://doi.org/10.1021/ja00281a038	journal	October 1986
Poly[1-(trimethylsilyl)-1-propyne]: a new high polymer synthesized with transition-metal catalysts and characterized by extremely high gas permeability Masuda, Toshio; Isobe, Eiji; Higashimura, Toshinobu Journal of the American Chemical Society, Vol. 105, Issue 25 https://doi.org/10.1021/ja00363a061	journal	November 1983
Triptycene ¹ (9,10-o-Benzenoanthracene) Bartlett, Paul D.; Ryan, M. Josephine; Cohen, Saul G. Journal of the American Chemical Society, Vol. 64, Issue 11 https://doi.org/10.1021/ja01263a035	journal	November 1942
Minimization of Internal Molecular Free Volume: A Mechanism for the Simultaneous Enhancement of Polymer Stiffness, Strength, and Ductility Tsui, Nicholas T.; Paraskos, Alex J.; Torun, Lokman Macromolecules, Vol. 39, Issue 9 https://doi.org/10.1021/ma060047q	journal	May 2006
Triptycene-Based Polymers of Intrinsic Microporosity: Organic Materials That Can Be Tailored for Gas Adsorption Ghanem, Bader S.; Hashem, Mohammed; Harris, Kenneth D. M. Macromolecules, Vol. 43, Issue 12 https://doi.org/10.1021/ma100640m	journal	June 2010
Intrinsically Microporous Soluble Polyimides Incorporating Tröger’s Base for Membrane Gas Separation Zhuang, Yongbing; Seong, Jong Geun; Do, Yu Seong Macromolecules, Vol. 47, Issue 10 https://doi.org/10.1021/ma5007073	journal	May 2014
Rational Design of Intrinsically Ultramicroporous Polyimides Containing Bridgehead-Substituted Triptycene for Highly Selective and Permeable Gas Separation Membranes Swaidan, Raja; Al-Saeedi, Majed; Ghanem, Bader Macromolecules, Vol. 47, Issue 15 https://doi.org/10.1021/ma5009226	journal	July 2014
Polymers of Intrinsic Microporosity Containing Trifluoromethyl and Phenylsulfone Groups as Materials for Membrane Gas Separation ^† Du, Naiying; Robertson, Gilles P.; Song, Jingshe Macromolecules, Vol. 41, Issue 24 https://doi.org/10.1021/ma801858d	journal	December 2008
Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes Wiegand, Jennifer R.; Smith, Zachary P.; Liu, Qiang J. Mater. Chem. A, Vol. 2, Issue 33 https://doi.org/10.1039/C4TA02303J	journal	January 2014
Free volume and intrinsic microporosity in polymers Budd, Peter M.; McKeown, Neil B.; Fritsch, Detlev Journal of Materials Chemistry, Vol. 15, Issue 20 https://doi.org/10.1039/b417402j	journal	January 2005
Highly permeable polymers for gas separation membranes Budd, Peter M.; McKeown, Neil B. Polymer Chemistry, Vol. 1, Issue 1 https://doi.org/10.1039/b9py00319c	journal	January 2010
Highly permeable chemically modified PIM-1/Matrimid membranes for green hydrogen purification Yong, Wai Fen; Li, Fu Yun; Chung, Tai-Shung Journal of Materials Chemistry A, Vol. 1, Issue 44 https://doi.org/10.1039/c3ta13308g	journal	January 2013
Positronium Annihilation in Molecular Substances Tao, S. J. The Journal of Chemical Physics, Vol. 56, Issue 11 https://doi.org/10.1063/1.1677067	journal	June 1972
Positron Annihilation as a Method to Characterize Porous Materials Gidley, David W.; Peng, Hua-Gen; Vallery, Richard S. Annual Review of Materials Research, Vol. 36, Issue 1 https://doi.org/10.1146/annurev.matsci.36.111904.135144	journal	August 2006
Positron Annihilation Spectroscopy Siegel, R. W. Annual Review of Materials Science, Vol. 10, Issue 1 https://doi.org/10.1146/annurev.ms.10.080180.002141	journal	August 1980

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