IP Library Granted Patent US 12,686,743
Granted Patent B2
US 12,686,743 · App. 17/946,007 · Granted Jul 21, 2026

Structured organic films containing imidazolium having cationic charge functionality and methods thereof

Inventors: Robert Claridge (Gilford, CA); Valerie M. Farrugia (Oakville, CA); David Lawton (Burlington, CA)
Assignee: GENESEE VALLEY INNOVATIONS, LLC
C08G65/48B01J41/13C08J5/2256H01M8/103H01M8/1067C08J2371/08H01M2008/1095
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,686,743
App. No.
17/946,007
Granted
Jul 21, 2026
Kind
B2
Abstract

A structured organic film (SOF) is disclosed including a plurality of segments, a plurality of linkers, and a plurality of ionic capping segments, where at least one or more ionic capping segments may include imidazolium. Implementations of the structured organic film (SOF) include where a concentration of ionic capping segments in the SOF is from about 0.1 to about 5.0 molar equivalents of ionic capping segments as compared to a concentration of nonionic segments in the SOF. A thickness of the SOF is from about 100 nm to about 500 μm. At least one of the plurality of ionic capping segments may include n-hydroxyethyl-1,2,4,5-tetramethylimidazolium (NETMImBr). At least one of the plurality of ionic capping segments may include n-hydroxypropyl-1,2,4,5-tetramethylimidazolium (NPTMImBr). An ion-exchange membrane may include the structured organic film (SOF).

Claims (23)

1 . A structured organic film (SOF), comprising:

a plurality of building block segments;

a plurality of linkers; and

a plurality of ionic capping segments, wherein at least one or more ionic capping segments comprises imidazolium; and

wherein a capped ionic network of the structured organic film comprises:

2 . The structured organic film (SOF) of claim 1 , wherein a thickness of the SOF is from about 100 nm to about 500 μm.

3 . The structured organic film (SOF) of claim 1 , wherein a capped ionic network of the structured organic film further comprises:

4 . An ion-exchange membrane, comprising the structured organic film (SOF) of claim 1 .

5 . The ion-exchange membrane of claim 4 , wherein the structured organic film (SOF) is free-standing.

6 . A structured organic film (SOF), comprising:

a plurality of building block segments; and

a plurality of linkers; wherein

at least one of the plurality of building block segments comprises:

and

wherein a capped ionic network of the structured organic film comprises:

7 . The structured organic film (SOF) of claim 6 , wherein a thickness of the SOF is from about 100 nm to about 500 μm.

8 . A structured organic film (SOF), comprising:

a plurality of building block segments; and

a plurality of linkers; wherein; and

at least one of the plurality of building block segments comprises:

and

wherein a capped ionic network of the structured organic film comprises:

9 . The structured organic film (SOF) of claim 8 , wherein a thickness of the SOF is from about 100 nm to about 500 μm.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073225/0116 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2022
From: CLARIDGE, ROBERT; FARRUGIA, VALERIE M.; LAWTON, DAVID
To: XEROX CORPORATION
Reel/Frame 061122/0303 →
Continuity (1)
Related Publication 20240110008A1 · Apr 4, 2024
References Cited (146)
US 3018272A · Griffing et al. · 1962 [cited by applicant]
US 5011956A · Ford et al. · 1991 [cited by applicant]
US 5119314A · Hotta et al. · 1992 [cited by applicant]
US 7108935B2 · Bauer et al. · 2006 [cited by applicant]
US 8029857B2 · Hoek et al. · 2011 [cited by applicant]
US 8093347B2 · Heuft et al. · 2012 [cited by applicant]
US 8119315B1 · Heuft et al. · 2012 [cited by applicant]
US 8264516B2 · Steven et al. · 2012 [cited by applicant]
US 8313560B1 · Cote et al. · 2012 [cited by applicant]
US 8318892B2 · Cote et al. · 2012 [cited by applicant]
US 8353574B1 · Heuft et al. · 2013 [cited by applicant]
US 8377999B2 · Cote et al. · 2013 [cited by applicant]
US 8389060B2 · Heuft et al. · 2013 [cited by applicant]
US 8410016B2 · Cote et al. · 2013 [cited by applicant]
US 8436130B2 · Cote et al. · 2013 [cited by applicant]
US 8518253B2 · Xiong et al. · 2013 [cited by applicant]
US 8529997B2 · Heuft et al. · 2013 [cited by applicant]
US 8591997B2 · Heuft et al. · 2013 [cited by applicant]
US 8652043B2 · Drucker et al. · 2014 [cited by applicant]
US 8765340B2 · Vella et al. · 2014 [cited by applicant]
US 8906462B2 · Wigglesworth et al. · 2014 [cited by applicant]
US 9097995B2 · Heuft et al. · 2015 [cited by applicant]
US 9309343B2 · Van Berchum et al. · 2016 [cited by applicant]
US 9375678B2 · Nair et al. · 2016 [cited by applicant]
US 9580824B2 · Masel et al. · 2017 [cited by applicant]
US 9768502B2 · Lin · 2017 [cited by applicant]
US 9815032B2 · Hill et al. · 2017 [cited by applicant]
US 9950549B2 · Kanungo et al. · 2018 [cited by applicant]
US 10076728B2 · Song et al. · 2018 [cited by applicant]
US 10258932B2 · Birss et al. · 2019 [cited by applicant]
US 10281831B2 · Cote et al. · 2019 [cited by applicant]
US 10347939B2 · Choi et al. · 2019 [cited by applicant]
US 10384441B2 · Badesha et al. · 2019 [cited by applicant]
US 10570524B2 · Matthews et al. · 2020 [cited by applicant]
US 10710065B2 · Helms et al. · 2020 [cited by applicant]
US 10792392B2 · Kourtis et al. · 2020 [cited by applicant]
US 10869950B2 · Kourtis et al. · 2020 [cited by applicant]
US 11053193B2 · Berghofer et al. · 2021 [cited by applicant]
US 20070055045A1 · Kiefer et al. · 2007 [cited by applicant]
US 20100147704A1 · Xiong et al. · 2010 [cited by applicant]
US 20100224867A1 · Heuft et al. · 2010 [cited by applicant]
US 20100228025A1 · Cote et al. · 2010 [cited by applicant]
US 20110217642A1 · Heuft et al. · 2011 [cited by applicant]
US 20110281197A1 · Daikoku et al. · 2011 [cited by applicant]
US 20120029236A1 · Cote · 2012 [cited by examiner]
US 20120296189A1 · Bhogal et al. · 2012 [cited by applicant]
US 20140054171A1 · Feldman et al. · 2014 [cited by applicant]
US 20140088207A1 · Elabd · 2014 [cited by examiner]
US 20140099571A1 · Proietti et al. · 2014 [cited by applicant]
US 20160251766A1 · Masel et al. · 2016 [cited by applicant]
US 20160259256A1 · Cote et al. · 2016 [cited by applicant]
US 20160293860A1 · Van Der Boom et al. · 2016 [cited by applicant]
US 20170240473A1 · Budarin et al. · 2017 [cited by applicant]
US 20190074710A1 · Hansen · 2019 [cited by applicant]
US 20190168173A1 · Tsapatsis et al. · 2019 [cited by applicant]
US 20190322114A1 · Sambhy et al. · 2019 [cited by applicant]
US 20200388871A1 · Newbloom et al. · 2020 [cited by applicant]
US 20210047242A1 · Liu et al. · 2021 [cited by applicant]
US 20220127396A1 · Hartmann-Thompson et al. · 2022 [cited by applicant]
US 20220223885A1 · Beh et al. · 2022 [cited by applicant]
US 20220282041A1 · Swager et al. · 2022 [cited by applicant]
US 20230250207A1 · Bae et al. · 2023 [cited by applicant]
US 20240279376A1 · Yoshimura · 2024 [cited by examiner]
CA 2833684A1 · 2013 [cited by applicant]
CN 107915658B · 2020 [cited by applicant]
EP 3476883A1 · 2019 [cited by applicant]
EP 3440239B1 · 2020 [cited by applicant]
WO WO2006016068A2 · 2006 [cited by applicant]
WO 2012045152A1 · 2012 [cited by applicant]
WO 2015178912A1 · 2015 [cited by applicant]
WO 2018143913A1 · 2018 [cited by applicant]
WO WO2018193021A1 · 2018 [cited by applicant]
WO 2022144900A1 · 2022 [cited by applicant]
WO WO2022249666A1 · 2022 [cited by examiner]
Li et al. Defective 2D Covalent Organic Frameworks for Postfunctionalization. Adv. Funct. Mater. 2020, 30, 1909267 (Year: 2020). [cited by examiner]
Agari et al., “Estimation of the compositional gradient in a PVC/PMMA graded blend prepared by the dissolutionediffusion method,” ScienceDirect, Polymer (2007) 1139-1147. [cited by applicant]
Alabi et al., “Electrostatically-coupled graphene oxide nanocomposite cation exchange membrane,” Journal of Membrane Science 594 (2020) 117457, 10 pages. [cited by applicant]
Banerjee et al., “Nafion Perfluorinated Membranes in Fuel Cells,” Journal of Fluorine Chemistry 125 (2004) 1211-1216, 6 pages. [cited by applicant]
Cho et al., “Engineering Synergy: Energy and Mass Transport in Hybrid Nanomaterials,” Advanced Materials 2015, 27, 5744-5752. [cited by applicant]
Chu et al., “Practical Implementation of bis-six-membered N-cyclic Quaternary Ammonium Cations in Advanced Anion Exchange Membranes for Fuel Cells: Synthesis and Durability,” Journal of Membrane Science 578 (2019) 239-2… [cited by applicant]
Claussen et al., “Longitudinal polymer gradient materials based on crosslinked polymers,” Polymer 55 (2014) 29-38. [cited by applicant]
Henkensmeier et al., “Overview: State-of-the Art Commercial Membranes for Anion Exchange Membrane Water Electrolysis,” Journal of Electrochemical Energy Conversion and Storage, May 2021, vol. 18, pp. 024001-1 through 02… [cited by applicant]
Holloczki et al., “Hydrolysis of Imidazole-2-ylidenes,” Journal of the American Chemical Society, 2011, 133, 780-789. [cited by applicant]
Inagi, “Fabrication of Gradient Polymer Surfaces Using Bipolar Electrochemistry,” Polymer Journal (2016) 48, 39-44. [cited by applicant]
Jaroszek et al., “Ion-exchange Membranes in Chemical Synthesis a Review,” Open Chem. (2015) 14, 1-19. [cited by applicant]
Kaczur et al., “Carbon Dioxide and Water Electrolysis Using New Alkaline Stable Anion Membranes,” Frontiers in Chemistry Technology Report, Jul. 2018, vol. 6, article 263, 16 pages. [cited by applicant]
Kaczur et al., “A Review of the Use of Immobilized Ionic Liquids in the Electrochemical Conversion of CO [cited by applicant]
Kandambeth et al., “Selective Molecular Sieving in Self-Standing Porous Covalent-Organic-Framework Membranes,” Advanced Materials 2017, 29, 1603945. [cited by applicant]
Kayser et al., “Cross-linked Sulfonated Poly(ether ether ketone) by Using Diamino-organosilicon for Proton Exchange Fuel Cells,” The Journal of Physical Chemistry B (2011) 115, 2916-2923. [cited by applicant]
Koshikawa et al., “Single Nanometer-Sized NiFe-Layered Double Hydroxides as Anode Catalyst in Anion Exchange Membrane Water Electrolysis Cell with Energy Conversion Efficiency of 74.7% at 1.0 A cm [cited by applicant]
Lee et al., “Poly(terphenylene) Anion Exchange Membranes: The Effect of Backbone Structure on Morphology and Membrane Property,” ACS Macro Letters (2017) 6, 566-570. [cited by applicant]
Li et al., “Recent advances in the fabrication of advanced composite membranes,” J. Mater. Chem. A, 2013, 1, 10058-10077. [cited by applicant]
Lin et al., Two-dimensional covalent triazine framework as an ultrathin-film nanoporous membrane for Desalination, Chem. Commun., 2015, 51, 14921-14924. [cited by applicant]
Liu et al., “Functional gradients and heterogeneities in biological materials: Design principles, functions, and bioinspired applications,” Progress in Materials Science (2017), 88, 467-498. [cited by applicant]
Lu et al., “A novel 3D covalent organic framework membrane grown on a porous α-Al [cited by applicant]
Meng et al., “2D and 3D Porphyrinic Covalent Organic Frameworks: The Influence of Dimensionality on Functionality,” Angew. Chem. 2020, 132, 3653-3658. [cited by applicant]
Meyers et al., “Structural Biological Materials: Critical Mechanics-Materials Connections,” Science, vol. 339, Feb. 15, 2013, 773-779. [cited by applicant]
Moon et al., Sufonated PEEK Ion Exchange Membranes for Direct Methanol Fuel Cell Applications, Macromolecular Research (2007) vol. 15, No. 4, pp. 379-384. [cited by applicant]
Oh et al., “In vitro and in vivo characteristics of PCL scaffolds with pore size gradient fabricated by a centrifugation method,” Biomaterials 28 (2007), 1664-1671. [cited by applicant]
Pedron et al, “Microfluidic approaches for the fabrication of gradient crosslinked networks based on poly(ethylene glycol) and hyperbranched polymers for manipulation of cell interactions,” Journal of Biomedical Materia… [cited by applicant]
Qiu et al., “Alkaline imidazolium- and quaternary ammonium-functionalized anion exchange membranes for alkaline fuel cell applications,” J. Mater. Chem., 2012, 22, 1040. [cited by applicant]
Ran et al., “Ion exchange membranes: New developments and applications,” Journal of Membrane Science 522 (2017) 267-291. [cited by applicant]
Suhaimin et al., “Methanol Permeability and Properties of Polymer Electrolyte Membrane Based on Graphene Oxidesulfonated (Polyether Ether) Ketone,” Malaysian Journal of Analytical Sciences, vol. 21, No. 2 (2017), 435-44… [cited by applicant]
Teng et al., “Preparation of Compositional Gradient Polymeric Films Based on Gradient Mesh Template,” Polymers (2018) 10, 677 (15 pages). [cited by applicant]
Varcoe et al., “Anion-exchange membranes in electrochemical energy systems,” Energy Environ. Sci., 2014, 7, 3135-3191. [cited by applicant]
Wang et al., “Efficient electrically powered CO [cited by applicant]
Wang et al., “N-cyclic quaternary ammonium-functionalized anion exchange membrane with improved alkaline stability enabled by aryl-ether free polymer backbones for alkaline fuel cells,” Journal of Membrane Science 587, … [cited by applicant]
Wang et al., “Novel Hydroxide-Conducting Polyelectrolyte Composed of an Poly(arylene ether sulfone) Containing Pendant Quaternary Guanidinium Groups for Alkaline Fuel Cell Applications,” Macromolecules 2010, 43, 3890-38… [cited by applicant]
Wang et al., “Stabilizing the Imidazolium Cation in Hydroxide-Exchange Membranes for Fuel Cells,” ChemSusChem 2013, 6, 2079-2082. [cited by applicant]
Yang et al., “Functionally graded membranes from nanoporous covalent organic frameworks for highly selective water permeation,” Journal of Materials Chemistry A, 2018, 6, 583-591. [cited by applicant]
Yang et al., The Application of Cation Exchange Membranes in Electrochemical Systems for Ammonia Recovery from Wastewater, Membranes 2021, 11, 494 (14 pages). [cited by applicant]
Yee et al., “The Effects of Sulfonated Poly(ether ether ketone) Ion Exchange Preparation Conditions on Membrane Properties,” Membranes 2013, 3, 182-195. [cited by applicant]
Zhang et al., “Novel cross-linked anion exchange membranes with diamines as ionic exchange functional groups and crosslinking groups,” International Journal of Hydrogen Energy 39 (2014) 13718-13724. [cited by applicant]
Wikipedia, “Sulfinic acid,” Wikipedia—The Free Encyclopedia, Wikipedia.org, 2025, 3 pages, retrieved from the internet on Jul. 9, 2025: https://en.wikipedia.org/w/index.php?title=Sulfinic_acid&oldid=1295112493. [cited by applicant]
Claridge, Robert, “Physically Reinforced Structured Organic Film (SOF) Anion Exchange Membranes (AEMs),” U.S. Appl. No. 18/229,427, filed Aug. 2, 2023, 49 pages. [cited by applicant]
Marino, M.G., et al., “Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids,” ChemSusChem., vol. 8, 2015 (Published online Nov. 27, 2014), pp. 513-523. [cited by applicant]
Min, K., et al., “Crosslinked poly(m-terphenyl N-methyl piperidinium)-SEBS membranes with aryl-ether free and kinked backbones as highly stable and conductive anion exchange membranes,” Journal of Membrane Science, vol.… [cited by applicant]
Yuan, Y., et al., “Preparation of an Anion Exchange Membrane by Pyridine-Functionalized Polyether Ether Ketone to Improve Alkali Resistance Stability for an Alkali Fuel Cell,” Energy Fuels, vol. 35, No. 4, Feb. 1, 2021,… [cited by applicant]
Kalla et al., “Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst,” Catalysis Letters, vol. 149, 2019 (Published … [cited by applicant]
Lancheros et al., “Development and Characterization of Poly(oxy-1-4-phenylenesulfonyl-1,4-phenylene) for Proton Exchange Membranes,” Journal of Applied Engineering Science, vol. 19, No. 4, Aug. 2021, pp. 1013-1019. [cited by applicant]
Extended European Search Report mailed in EP 23193650.1 on Feb. 19, 2024. (9 pages). [cited by applicant]
Extended European Search Report for European Application No. 23193647.7 dated Feb. 5, 2024, 9 pages. [cited by applicant]
Extended European Search Report for European Application No. 23193651.9 dated Feb. 2, 2024, 18 pages. [cited by applicant]
Extended European Search Report mailed in EP 23196462.8 on Mar. 12, 2024. (8 Pages). [cited by applicant]
Aggarwal et al., “Ligand Valency Effects on the Alkaline Stability of Metallopolymer Anion-Exchange Membranes,” Macromolecular Rapid Communications, vol. 42, Article 2100238, 2021 (Published online Jun. 25, 2021), 6 pag… [cited by applicant]
Disabb-Miller et al., “Water Uptake and Ion Mobility in Cross-Linked Bis(terpyridine)ruthenium-Based Anion Exchange Membranes,” Macromolecules, vol. 46, 2013 (Published Nov. 22, 2013), pp. 9279-9287. [cited by applicant]
Kwasny et al., “Expanding metal cation options in polymeric anion exchange membranes,” Journal of Materials Chemistry A, vol. 5, 2017 (Published Dec. 5, 2016), pp. 1400-1405. [cited by applicant]
Leech et al., “Effect of Composition of Polymer Backbone on Spectroscopic and Electrochemical Properties of Ruthenium(II) Bis(2,2′-bipyridyl)-containing 4-Vinylpyridine/Styrene Copolymers,” Journal of Materials Chemistr… [cited by applicant]
Yuan et al., “Ring-opening metathesis polymerization of cobaltocenium derivative to prepare anion exchange membrane with high ionic conductivity,” Polyhedron, vol. 181, Article 114462, 2020 (Available online Mar. 2, 202… [cited by applicant]
Zha et al., “Metal-Cation-Based Anion Exchange Membranes,” Journal of the American Chemical Society (JACS), vol. 134, 2012 (Published Mar. 2, 2012), pp. 4493-4496. [cited by applicant]
Zhu et al., “Cationic Metallo-Polyelectrolytes for Robust Alkaline Anion-Exchange Membranes,” Author Manuscript, Angew. Chem. Int. Ed., vol. 57, No. 9, Feb. 23, 2018 (First published Dec. 31, 2017), pp. 2388-2392 (7 pag… [cited by applicant]
Zhu et al., “Rational Synthesis of Metallo-Cations Toward Redox- and Alkaline-Stable Metallo-Polyelectrolytes,” Journal of the American Chemical Society (JACS), vol. 142, 2020 (Published Dec. 17, 2019), pp. 1083-1089. [cited by applicant]
Farrugia, V.M., et al., “Gradient Membranes Formed From Free Standing Structured Organic Films and Methods Thereof,” U.S. Appl. No. 17/946,001, filed Sep. 15, 2022, 42 pages. [cited by applicant]
Farrugia, V.M., et al., “Cation Exchange Membranes From Structured Organic Films and Methods Thereof,” U.S. Appl. No. 17/946,003, filed Sep. 15, 2022, 39 pages. [cited by applicant]
Farrugia, V.M., et al., “Anion Exchange Membranes From Structured Organic Films and Methods Thereof,” U.S. Appl. No. 17/946,006, filed Sep. 15, 2022, 38 pages. [cited by applicant]
Claridge, R., et al., “Structured Organic Films Containing N-Cyclic Quaternary Ammonium Having Cationic Charge Functionality and Methods Thereof,” U.S. Appl. No. 18/051,800, filed Nov. 1, 2022, 42 pages. [cited by applicant]
Morimitsu, K., et al., “Ion Exchange Membranes (IEMS) With Ionic Ligand-Metal Complexes and Methods Thereof,” U.S. Appl. No. 18/169,098, filed Feb. 14, 2023, 17 pages. [cited by applicant]
Farrugia, V., et al., “Flexible Structured Organic Film Membrane Formulations and Methods Thereof,” U.S. Appl. No. 18/218,420, filed Jul. 5, 2023, 43 pages. [cited by applicant]
Claridge, R., et al., “Flexible Ionic Building Blocks With High Ionic Conductivity and Alkaline Stability for Use in Structured Organic Film (SOF) Containing Anion Exchange Membranes (AEMs),” U.S. Appl. No. 18/218,445, … [cited by applicant]
Guo et al., “A quaternary-ammonium-functionalized covalent organic framework for anion conduction,” CrystEngComm (The Royal Society of Chemistry), vol. 19, 2017 (Published on Apr. 18, 2017), pp. 4905-4910 (7 pages total… [cited by applicant]
Abruña, H.D., “Fuel Cells—Alkaline Anion Exchange Membranes,” The Department of Chemistry & Chemical Biology, Abruna Electrochemistry, publication date unknown (retrieved from the internet on Sep. 6, 2022), 5 pages, htt… [cited by applicant]
Agnew, N.H., “Transition Metal Complexes of Poly(vinylpyridines),” Journal of Polymer Science: Polymer Chemistry Edition, vol. 14, 1976, pp. 2819-2830. [cited by applicant]
Author Unknown, “Polymer (matrix) structure—A236,” CKN Knowledge in Practice Centre, publication date unknown (retrieved from the internet on Sep. 6, 2022), 7 pages, https://compositeskn. org/KPC/A236—Web Page last edit… [cited by applicant]
Non-Final Office Action for U.S. Appl. No. 18/169,098, dated Feb. 12, 2026. [cited by applicant]
Ma, H. et al., “Free-standing poly(2-vinylpyridine) foam films doped with silver nanoparticles formed at the planar liquid/liquid interface,” Journal of Colloid and Interface Science, Jan. 3, 2013, 8 pages. [cited by applicant]
Kang, et al., “Free-standing, polysilsesquioxane-based inorganic/organic hybrid membranes for gas separations,” Journal of Membrane Science 475 (2015), 384-394. [cited by applicant]