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COF–COF Bilayer Membranes for Highly Selective Gas Separation Hongwei Fan, Alexander Mundstock, Armin Feldhoff, Alexander Knebel, Jiahui Gu, Hong Meng, and Jürgen Caro J. Am. Chem. Soc., Just Accepted Manuscript • Publication Date (Web): 18 Jul 2018 Downloaded from http://pubs.acs.org on July 18, 2018
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Journal of the American Chemical Society
COF–COF Bilayer Membranes for Highly Selective Gas Separation Hongwei Fan,*,†,‡ Alexander Mundstock,† Armin Feldhoff,† Alexander Knebel,† Jiahui Gu,‡ Hong Meng,‡ and Jürgen Caro*,† †
Institute of Physical Chemistry and Electrochemistry, Leibniz Universität Hannover, Callinstraße 3A, D-30167 Hannover, Germany ‡ College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, PR China
Supporting Information Placeholder ABSTRACT: Covalent organic frameworks (COFs) have been proposed as alternative candidates for molecular sieving membranes due to their chemical stability. However, developing COF membranes with narrowed apertures close to the size of common gas molecules is a crucial task for selective gas separation. Herein, we demonstrate a new type of a two-dimensional layeredstacking COF-COF composite membrane in bilayer geometry synthesized on a porous support by successively regulating the growth of imine-based COF-LZU1 and azine-based ACOF-1 layers via a temperature-swing solvothermal approach. The resultant COF-LZU1–ACOF-1 bilayer membrane has much higher separation selectivity for H2/CO2, H2/N2, and H2/CH4 gas mixtures than the individual COF-LZU1 and ACOF-1 membranes due to the formation of interlaced pore networks, and the overall performance surpasses the Robeson upper bounds. The COFLZU1–ACOF-1 bilayer membrane also shows high thermal and long-time stabilities.
Covalent-organic frameworks (COFs) represent a novel class of porous crystalline materials based on the atomically precise integration of organic building blocks into highly ordered and periodic two-dimensional (2D) or three-dimensional (3D) network structures.1 The COFs have received tremendous scientific attention because of their potential applications including gas storage, molecular separation, catalysis, optoelectronics, and energy storage.2 Specifically, apart from the inherent properties of permanent porosity, well-defined pore aperture, ordered channel structure and large surface area, COFs based on Schiff base-type linkages3 such as imine-, azine-, hydrazone- or enamine-linked COFs4 are found to be superior to other COFs and metal–organic frameworks (MOFs)5. These properties make the Schiff base-type COFs attractive candidates for robust molecular sieving membranes. As compared to the 3D-COFs, 2D-COFs in form of lamellar atomthick sheets6 are highly desirable for the construction of thin membranes with minimal transport resistance.7 Moreover, unlike other 2D layered-MOFs or graphene oxide relying primarily on the precise tuning of interlayer spacing,8 the intrinsic merits of abundant and well-ordered in-plane pores within the nanosheets9 realize the 2D-COFs ultra-fast and highly selective molecular sieving. However, despite some attempts made to study COF-based mixed matrix membranes10 and COF membranes11, progress is very limited and there are only a very few reports of continuous
COF films as sieving membranes for gas separations.12 One problem is to fabricate a defect-free thin COF layers strongly attached to the support surface.13 Another problem is the pore size of Schiff base-type COFs (typically 0.8-5 nm) 3,14 which is remarkably larger than the kinetic diameter of gas molecules (about 0.250.5 nm).15 The introduction of functional groups in COFs to narrow the pore size through a bottom-up synthesis approach or postsynthesis treatment16 is one way to enhance the gas selectivity of COFs. Although the reported MOF-COF composite membrane shows a higher separation selectivity (about 12-14) for H2/CO2 than the individual COF and MOF membranes (with selectivities of 6, and 7-9, respectively), the improvement was not as high as expected.12b In 2D-COF geometries, there are two structural arrangements. One is the eclipsed layered-sheet stacking (AA stacking) in which atoms of adjacent layers lie directly over each other, and the other is a staggered layered-sheet stacking (AB stacking) that can be regarded as two adjacent layers offset against each other.17 Most of the reported Schiff base-type 2D-COFs features the more stable eclipsed stacking structure with a periodic alignment of πcolumns due to the lower energy.17a-c Inspired by the staggered stacking mode, we developed a novel supported COF-COF bilayer membrane by growing a 2D-COF layer on the other 2DCOF layer, which has the layered-stacking structure with interlaced pore network. The resulting membrane is similar to a pile of sieves with large and small holes with excellent sieving selectivity for gas separations. In this study we choose the 2D-COFs of imine-linked COFLZU1 (LZU stands for Lanzhou University, Figure S1a)18 and azine-linked ACOF-1 (A stems from azine) (Figure S1b)19 as the building blocks for constructing the COF-LZU1–ACOF-1 bilayer membrane, because they are both of hexagonal pore structure with aperture size of ∼1.8 nm and ∼0.94 nm, respectively.18,19 It can be expected, therefore, that the formed interlaced pores of the COFLZU1–ACOF-1 membrane are in the appropriate size range of the kinetic diameter of gas molecules. Whereas, the synthesis of COF-LZU1 is fast performed by condensation of 1,3,5triformylbenzene (TFB) with p-phenylenediamine (PDA) at room temperature, the synthesis of high-crystallinity ACOF-1 by condensation of TFB with hydrazine hydrate takes place at higher temperatures.20 Following ref. 20, COF-LZU1 is formed easily due to the stronger π−π stacking interactions of the aromatic rings of TFB and PDA and the π-systems of oligomers during the start of layer formation and the subsequent error-correction process. So, a facile temperature-swing solvothermal synthesis is proposed to
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Figure 1. (a) Schematic representation of synthesis of COF-LZU1–ACOF-1 bilayer membrane by a temperature-swing solvothermal approach. (b) Schematic illustration of the reactions and growth of COF-COF membranes. fabricate the COF-LZU1–ACOF-1 bilayer membrane (Figure 1a). about 1 µm thick featuring a layered-stacking structure, but withFirst, an Al2O3 disk (18 mm in diameter) was sequentially treated out obvious boundary between the two COF layers. A possible with 3-aminopropyltriethoxysilane (APTES), TFB and the reason might be that the ACOF-1 started to grow inside the COFPDA/hydrazine hydrate mixture. Then, the dual-aminoLZU1 framework. The layer thickness of a single COF-LZU1-72h functionalized Al2O3 disk was placed horizontally face up in a membrane (Figure S8), synthesized by using the same feed soluTeflon-lined stainless steel autoclave with synthesis solution (60 tion and procedure but stopped after 72 h at room temperature was mg TFB, 30 mg PDA in 5 mL dioxane with 0.5 mL 6M acetic found to be about 450 nm. Subtracting this value from the thickacid, 19 µL hydrazine hydrate). The stainless steel autoclave was ness of the bilayer membrane (Figure 2b and c) gives a thickness left at room temperature for 72 h to allow the COF-LZU1 layer to of about 550 nm for the ACOF-1 top layer. Energy-dispersive Xgrow on the support surface via imine condensation of TFB and ray spectroscopy (EDXS) (Figure 2c and d) reveals sharp transiPDA (Figure 1b-i,ii), and then heated at 120 °C for 72 h for the tion between the COF-LZU1–ACOF-1 layers (C signals) and the growth of the ACOF-1 layer by condensation of the residual alumina support (Al signals). A typical XRD pattern (Figure S9) amount of TFB and hydrazine hydrates (Figure 1b-iii). of the COF-LZU1–ACOF-1 membrane further indicates that the layer consists of only COF-LZU1 and ACOF-1 without impurity phases. The main reason for the high-quality and layered-stacking of the COF-LZU1–ACOF-1 bilayer membrane is that the dualamino grafting with PDA and hydrazine hydrate served as a surface modifier for coordination bonds between TFB and the substrate. In a control experiment (Figure S10) at room temperature only a COF-LZU1 layer but no ACOF-1 layer could be grown. Also the sequential formation of the COF-LZU1 layer and the ACOF-1 layer could be verified from the morphological change of the growing crystals as detected by SEM and XRD patterns of the COF-COF powders (Figure S11). The stacking-layered structure results in an interlaced pore network of the COF-LZU1– ACOF-1 bilayer membrane, which can be directly proven through the collected COF powders from the same reactor. The corresponding experimental pore size distribution (EPSD) was determined from nitrogen adsorption–desorption isotherms. As shown in Figure S12, the measured BET surface area of COF-LZU1– Figure 2. SEM images of the (a) top view with inserted digital ACOF-1 is 386 m2·g-1, and the EPSD is concentrated in the range photograph (bottom-left corner), (b,c) cross-sectional views of the of 0.3-0.5 nm, both data are less than the individual data of COFsupported COF-LZU1–ACOF-1 bilayer membrane. (d) EDXS LZU1 (~ 1.87 nm) and ACOF-1 (~ 0.99 nm) due to the formation mapping of the membrane cross-section and corresponding eleof massive reticulate pores. This EPSD also illustrates that the mental distributions. C Kα1_2 signal, red; Al Kα1 signal, green. pore size was effectively decreased by intergrowth of the 2DThe white Al2O3 disk became claybank (see inset in Figure 2a), layered COFs nanosheets, which is in complete accordance with indicating that a COF-LZU1–ACOF-1 was grown onto the subthe gas permeation studies. strate. The SEM top view (Figure 2a and S2a) shows that a conBefore gas permeation, an on-stream activation was carried out tinuous COF-LZU1–ACOF-1 layer with well-intergrown grains at 393 K to eliminate solvent molecules by using an equimolar (500 nm to 1 µm in size) was formed. No cracks, pinholes, or H2/CH4 mixture (Figure S13). The fluxes of the single gases H2, other defects are visible. Moreover, PXRD, SEM and TEM charCO2, N2, and CH4 as well as 1:1 binary mixtures of H2 with CO2, acterizations (Figure S3-S7) of the COF powders collected from N2, and CH4 through the membrane were measured at room temthe same reactor in which the membrane was formed, confirmed perature (298 K), 1 bar, and the results are summarized in Figure the coexistence of COF-LZU1 and ACOF-1 with high crystallini3 and Table S1. From both it can be seen that for the COF-LZU1– ty. As shown in Figure 2b, the COF-LZU1–ACOF-1 layer is ACOF-1 bilayer membrane, the H2 permeance of 2.45 × 10−7
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Journal of the American Chemical Society mol·m−2·s−1·Pa−1 is much higher than those of the other gases, and a cut-off is clearly observed between the H2 and other more bulky gases. This shows the molecular sieve performance of COFLZU1–ACOF-1 bilayer membrane. The ideal separation factors (ISFs) of H2 from CO2, N2 and CH4, determined as the ratio of the single component permeances are 26.7, 88.7, 105.0, respectively, which considerably exceed the corresponding Knudsen constants. That is to say, the COF-LZU1–ACOF-1 bilayer membrane is expected to display desirable hydrogen selectivity in mixed-gas permeation via molecular sieving.
Figure 3. Single-gas permeances of the COF-LZU1–ACOF-1 bilayer membrane as a function of the kinetic diameter of permeating molecules at 298 K, 1 bar. The inset shows the mixed gas separation factor for H2 over other gases. As shown in Figure 3, the mixed gas SFs of the COF-LZU1– ACOF-1 bilayer membrane for equimolar H2/CO2, H2/N2, and H2/CH4 gas pairs reach 24.2, 83.9, 100.2, respectively, which are only slightly smaller than the predictions from the ISFs. We also fabricated the pure COF-LZU1 membrane (Figure S14) and pure ACOF-1 membrane (Figure S15), and applied them for comparison in the same gas permeation measurements (Figure S16, S17, Table S1). As shown from Table S1, the mixed gas SFs of H2/CO2, H2/N2, H2/CH4 for the COF-LZU1–ACOF-1 bilayer membrane greatly surpass those for the two pure COF membranes, while the H2 permeability is only slightly decreased due to (i) the narrowed pores (Figure S18) and (ii) the thicker COF-COF bilayer (~ 1 µm) compared with the pure COF-LZU1 layer (~ 500 nm) and the pure ACOF-1 layer (~ 600 nm). Moreover, the mixed gas SFs (Figure S19) for the COF-LZU1-72h membrane are also far lower than the COF-LZU1–ACOF-1 bilayer membrane, despite with a relatively high H2 permeance. As shown in Figure S20, with the increase of permeation temperature from 298 to 393 K, the H2 permeance increased from 1.9 × 10−7 mol·m−2·s−1·Pa−1 to 5.0 × 10−7 mol·m−2·s−1·Pa−1 while the H2/CH4 selectivity was only slightly reduced from 105 to 93. This finding demonstrates the high thermal stability of the COFLZU1–ACOF-1 bilayer membrane. Moreover, the COF-LZU1– ACOF-1 bilayer membrane keeps its high H2/CH4 selectivity with increasing H2 partial pressure from 0.5 to 0.8 bar corresponding to total feed pressures of 1.0 to 1.6 bar (Figure S21). In addition, the COF-LZU1–ACOF-1 bilayer membrane was evaluated in a continuous gas permeation measurement of H2/CH4 for over 100 h at 298 K, and its separation performance was scarcely degraded, indicating a good running stability (Figure S22).
Figure 4. Mixed gas selectivities of (a) H2/CO2, (b) H2/N2, and (c) H2/CH4, as a function of H2 permeability for our two pure COF membranes and the COF-COF bilayer membrane compared with literature data. Figure 4 shows the selectivity for the binary mixtures H2/CO2, H2/N2, and H2/CH4 as a function of the H2 permeability for the three membranes under study in comparison with literature data. Notably, the COF-LZU1–ACOF-1 membrane shows high values of both permeability and selectivity in comparison with other membranes, and surpasses the latest Robeson upper bounds21 (a detailed comparison is shown in Table S2-S4). The selectivity increase is explained by the formed interlaced pores close to the size of common gas molecules, and the high permeability is due to the thin COF-COF layer of only about 1 µm. In conclusion, we have developed a novel 2D layered-stacking COF-COF membrane supported on dual-amino modified alumina substrate via a facile temperature-swing solvothermal synthesis
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approach. Due to the formation of an interlaced pore network in the contact zone, the COF-COF bilayer membrane shows a higher selectivity for the separation of H2 from other more bulky gases than the individual COF counterparts. The excellent molecular sieving performances of the COF-LZU1–ACOF-1 membrane surpass the 2008 Robeson upper bounds for H2/CO2, H2/N2, and H2/CH4 mixture by far. Due to the strong covalent imine bonding, the COF-COF membrane also displays high thermal and longtime operational stabilities. Our COF-LZU1–ACOF-1 bilayer membrane not only provides a promising candidate for hydrogen production and purification, but also a new concept for pore engineering of COFs.
ASSOCIATED CONTENT Supporting Information The Supporting Information is available free of charge on the ACS Publications website. Experimental procedures, characterization data, and the separation performance comparison of various membranes (PDF).
AUTHOR INFORMATION Corresponding Author *
[email protected] and
[email protected] Notes The authors declare no competing financial interests.
ACKNOWLEDGMENT Financial support from the Sino-German (CSC-DAAD) Postdoc Scholarship Program, 2017 (57343410), the program of China Scholarships Council (CSC NO. 201709920078), and the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – FE928/15-1 and Ca 147/21 is gratefully acknowledged. The authors thank Dr. Sebastian Friebe for valuable discussion and Frank Steinbach for TEM measurement.
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Journal of the American Chemical Society 2011, 17, 2388. (d) B. T. Koo, W. R. Dichtel and P. Clancy, J. Mater. Chem., 2012, 22, 17460. (18) Ding, S. Y.; Gao, J.; Wang, Q.; Zhang, Y.; Song, W. G.; Su, C. Y.; Wang, W. J. Am. Chem. Soc. 2011, 133, 19816. (19) (a) Li, Z.; Feng, X.; Zou, Y.; Zhang, Y.; Xia, H.; Liu, X.; Mu,Y. Chem. Commun. 2014, 50, 13825. (b) Stegbauer, L.; Hahn, M. W.; Jentys, A.; Savasci, G.; Ochsenfeld, C.; Lercher, J. A.; Lotsch, B. V. Chem. Mater. 2015, 27, 7874. (20) Peng, Y.; Wong, W. K.; Hu, Z.; Cheng, Y.; Yuan, D.; Khan, S. A.; Zhao, D. Chem. Mater. 2016, 28, 5095. (21) (a) Robeson, L. M. J. Membr. Sci. 1991, 62, 165. (b) Robeson, L. M. J. Membr. Sci. 2008, 320, 390.
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