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Fast, Ambient Temperature and Pressure Ionothermal Synthesis of Three-Dimensional Covalent Organic Frameworks Xinyu Guan, Yunchao Ma, Hui Li, Yusran Yusran, Ming Xue, Qianrong Fang, Yushan Yan, Valentin Valtchev, and Shilun Qiu J. Am. Chem. Soc., Just Accepted Manuscript • DOI: 10.1021/jacs.8b01320 • Publication Date (Web): 19 Mar 2018 Downloaded from http://pubs.acs.org on March 19, 2018

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Journal of the American Chemical Society

Fast, Ambient Temperature and Pressure Ionothermal Synthesis of Three-Dimensional Covalent Organic Frameworks Xinyu Guan,† Yunchao Ma,† Hui Li,† Yusran Yusran,† Ming Xue,† Qianrong Fang,∗,† Yushan Yan,‡ Valentin Valtchev†,∥ and Shilun Qiu† †State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, P. R.

China ‡Department of Chemical and Biomolecular Engineering, Center for Catalytic Science and Technology, University of

Delaware, Newark, DE 19716, USA ∥

Normandie Univ, ENSICAEN, UNICAEN, CNRS, Laboratoire Catalyse et Spectrochimie, 6 Marechal Juin, 14050 Caen, France

Supporting Information Placeholder ABSTRACT: Covalent organic frameworks (COFs) are an emerging class of porous crystalline polymers with wide range of potential applications. However, the availability of three-dimensional (3D) COFs is still limited, and their synthesis is confined to the high-temperature solvothermal method. Here, we report for the first time a general and simple strategy to produce a series of 3D ionic liquid (IL)-containing COFs (3D-IL-COFs) by using IL as a green solvent. The syntheses are carried out at ambient temperature and pressure accompanied by a high reaction speed (e.g., only three mins for 3D-ILCOF-1), and the IL can be reused without activity loss. Furthermore, the 3D-IL-COFs show impressive performance in the separation of CO2/N2 and CO2/CH4. This research thus presents a potential pathway to green large-scale industrial production of COFs.

Covalent organic frameworks (COFs) are a new class of crystalline porous polymer materials, which are composed of light elements (typically C, H, N, B, O) and linked by covalent bonds.1-4 Over the past decade, COFs have attracted considerable attention in various fields including gas adsorption and separation,5-7 catalysis,8,9 electrochemistry,10,11 and a number of others.12-17 Yet most of published COFs are twodimensional (2D) structures, and the preparation of new three-dimensional (3D) COFs remains a challenge.18-25 Meanwhile, the classical preparation method of 3D COFs so far is limited to the solvothermal synthesis, which is carried out at elevated temperatures and pressures in sealed tubes, and results in high energy consumption, complex operations and possible release of volatile organic compounds (VOC). Thus, the development of a simple, mild and green synthetic route for COF materials is highly desirable, especially for the largescale industrial productions and applications. Ionic liquids (ILs) are organic salts which have low melting point (e.g., lower than 100 °C) and consist only of ions in liquid phase. Applications of ILs in different fields have been

Scheme 1. Strategy for preparing 3D ionic liquidcontaining COFs (3D-IL-COFs)a

aCondensation

of tetrahedral tetrakis(4formylphenyl)methane (TFPM) and three expanded linear links, p-phenylenediamine (PDA), 4,4'-diaminobiphenyl (DABP), and 4,4''-diamino-p-terphenyl (DATP), to give a series of 3D-IL-COFs based on the open system at RT by using [BMIm][NTf2] as green solvent. studied extensively, such as chemical reaction, extraction, catalysis and gas absorption.26 ILs have recently drawn broad attentions as green and safe reaction media for the synthesis of crystalline materials, such as zeolites27 and metal-organic frameworks (MOFs),28,29 due to their peculiar properties including negligible vapor pressure, non-flammable, wide liquid range, good solubility for both organic and inorganic com-

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pounds and highly designable structure.30 However, no COFs have been synthesized by using ILs as reaction solvents so far. Herein we report a general and simple approach to construct 3D COFs by ambient temperature and pressure ionothermal synthesis in an open system. Based on this strategy, a series of 3D IL-containing COFs (3D-IL-COFs) with multi-fold interpenetrated diamondoid (dia) nets, denoted 3D-IL-COF-1, 3D-IL-COF-2 and 3D-IL-COF-3 respectively, were successfully prepared. More importantly, 3D-IL-COFs can be synthesized for short period of time (e.g., three mins synthesis of 3D-ILCOF-1), and IL can be reused by a simple filtration for at least three times without significant activity loss. Furthermore, based on the high crystallinity and porosity of COFs and good affinity to CO2 of ILs, 3D-IL-COFs display outstanding selectivity in the separation of CO2 from air (N2) and natural gas (CH4). To the best of our knowledge, this study is the first case for the ambient temperature and pressure ionothermal synthesis of COF materials.

Figure 1. PXRD patterns of 3D-IL-COF-1 (a), 3D-IL-COF-2 (b) and 3D-IL-COF-3 (c).

In the pursuit of 3D-IL-COFs, 1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide ([BMIm][NTf2]), which is a liquid at room temperature (RT), was chosen as both solvent and catalyst for the Schiff base reaction.26,30 In the IL solvent, the tetrahedral building blocks, tetrakis(4formylphenyl)methane (TFPM), reacts with the linear links of increasing size, p-phenylenediamine (PDA, 6.1 Å), 4,4'diaminobiphenyl (DABP, 10.7 Å) or 4,4''-diamino-p-terphenyl (DATP, 15.3 Å), to produce the extended 3D interpenetrated dia structures, 3D-IL-COF-1, 3D-IL-COF-2 and 3D-IL-COF-3 respectively (Scheme 1).31 Typically, the syntheses were carried out by suspending TFPM (21.6 mg, 0.05 mmol) and PDA (10.8 mg, 0.1 mmol), DABP (18.4 mg, 0.1 mmol) or DATP (26.1 mg, 0.1 mmol) in [BMIm][NTf2] (100 μL) followed by keeping at ambient temperature and pressure to give crystalline solids. These 3D-ILCOFs can be synthesized within 12 hrs, which is substantially shorter than those from the traditional solvothermal method (3-7 days). Remarkably, highly crystalline 3D-IL-COF-1 was synthesized for only three mins (Figure S1). The [BMIm][NTf2] was separated by a simple filtration and reused for at least three times without activity loss (Figure S2).

Figure 2. Structural representations of 3D-IL-COF-1 (a and b), 3D-IL-COF-2 (c and d) and 3D-IL-COF-3 (e and f). C, blue; H, gray; N, red.


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Journal of the American Chemical Society Complementary methods were employed for detailed structural characterization of the new COFs. The morphology of 3D-IL-COFs was examined by scanning electron microscopy (SEM), and the COF crystals range between 0.5 and 1.0 µm in size and form complex aggregates (Figures S3-5). Fourier transform infrared (FTIR) spectra displayed peaks around 1624 cm−1 for 3D-IL-COF-1, 1622 cm−1 for 3D-IL-COF-2, 1623 cm−1 for 3D-IL-COF-3, corresponding to C=N stretching vibrations, thus indicating the occurrence of the condensation. Two absorptions at 1355 and 1061 cm-1 for 3D-IL-COF-1, 1364 and 1060 cm−1 for 3D-IL-COF-2, 1363 and 1062 cm−1 for 3D-ILCOF-3, corresponding to the vibration modes of [NTf2]- anions: SO2 asymmetric stretching (as) and SNS asymmetric stretching (as) modes, provide the evidence that ILs have been confined into COFs (Figures S6-8). The solid state 13C crosspolarization magic-angle-spinning (CP/MAS) NMR spectra further confirmed the presence of carbon from the C=N bond at 158 ppm for 3D-IL-COF-1, 159 ppm for 3D-IL-COF-2, 157 ppm for 3D-IL-COF-3, respectively (Figures S9-11). According to the thermogravimetric analysis (TGA), 3D-IL-COFs contain 8-12% ILs in their pores and show high thermal stability (up to 450 °C) under nitrogen (Figures S12-14).

agreement with the experimental ones (Figure 1). Furthermore, full profile pattern matching (Pawley) refinements were carried out on the experimental PXRD patterns. Peaks at 7.27, 10.39, 10.53, 14.76 and 18.49° 2θ for 3D-IL-COF-1 correspond to the (200), (220), (301), (321) and (411) Bragg peaks of space group I41/a (No. 88), respectively; peaks at 5.92, 8.49, 12.15 and 13.46° 2θ for 3D-IL-COF-2 correspond to the (200), (220), (400) and (420) Bragg peaks of space group I41/a (No. 88), respectively; and peaks at 5.19, 7.35, 10.40, 11.64 and 14.74° 2θ for 3D-IL-COF-3 correspond to the (200), (220), (400), (420) and (411) Bragg peaks of space group I41/a (No. 88), respectively. The refinement results yield unit cell parameters nearly equivalent to the predictions with good agreement factors (a = b = 23.7733 Å, c = 13.4608 Å, α = β = γ = 90°, ωRp = 3.77% and Rp = 2.58% for 3D-IL-COF-1; a = b = 29.4089 Å, c = 7.7431 Å, α = β = γ = 90°, ωRp = 5.06% and Rp = 3.98% for 3D-IL-COF-2; a = b = 33.9708 Å, c = 7.6236 Å, α = β = γ = 90°, ωRp = 3.81% and Rp = 2.59% for 3D-IL-COF-3). Some peaks after 18° 2θ in these IL-containing COFs are stronger than calculated due to the presence of ionic liquid guests in the micropore space, which is similar to those reported for COFs with alkyl chains or other guest molecules in their pores.33,34 On the basis of the above results, 3D-IL-COFs are proposed to have the expected architectures with 5-fold, 9-fold or 11-fold interpenetrated dia net (Tables S1-3), and show microporous cavities with a diameter of about 7.9 Å for 3D-IL-COF-1, 10.2 Å for 3D-IL-COF-2, and 12.1 Å for 3D-ILCOF-3 (Figure 2). Notably, 3D-IL-COF-3 with 11-fold interpenetrated dia net represents the most interpenetrated framework for COFs reported to date. Nitrogen (N2) adsorption-desorption isotherms were conducted at 77 K to evaluated the porosity of 3D-IL-COFs. As can be seen in Figure 3a, a sharp gas uptake is observed at low pressure (below 0.1 P/P0) for 3D-IL-COFs, which reveals their microporous nature. The inclination of isotherms in the 0.81.0 P/P0 range shows the presence of textural mesopores, which is the consequence of the agglomeration of COF crystals.25 The Brunauer-Emmett-Teller (BET) surface area is 517 m2 g-1 for 3D-IL-COF-1, 653 m2 g-1 for 3D-IL-COF-2 and 870 m2 g-1 for 3D-IL-COF-3 (Table 1 and Figures S15-17). The total pore volume was calculated at P/P0 = 0.8 to be 0.36 cm3 g-1 for 3D-IL-COF-1, 0.53 cm3 g-1 for 3D-IL-COF-2 and 0.56 cm3 g-1 for 3D-IL-COF-3. The pore-size distributions of 3D-IL-COFs were calculated by nonlocal density functional theory (NLDFT), and they showed a narrow pore width (8.3 Å for 3D-IL-COF-1, 10.7 Å for 3D-IL-COF-2 and 12.4 Å for 3D-IL-COF-3, Figures S1820), which is in good agreement with the pore size predicted from their crystal structures.

Figure 3. N2 adsorption-desorption isotherms (a), CO2 separation properties for isoreticular 3D-IL-COF-1 (b), 3D-IL-COF2 (c) and 3D-IL-COF-3 (d), and breakthrough curves for 3D-ILCOF-1 using the CO2/N2 (e) and CO2/CH4 (f) gas mixture. The unit cell parameters of 3D-IL-COFs were resolved by the powder X-ray diffraction (PXRD) pattern measurements in conjunction with structural simulations. After a geometrical energy minimization by using the Materials Studio software package32 based on the 5-fold, 9-fold or 11-fold interpenetrated dia net for 3D-IL-COF-1, 3D-IL-COF-2 and 3D-IL-COF-3 respectively, the unit cell parameters were obtained (a = b = 23.6865 Å, c = 13.3002 Å and α = β = γ = 90° for 3D-IL-COF-1; a = b = 29.7181 Å, c = 7.7366 Å and α = β = γ = 90° for 3D-ILCOF-2; a = b = 33.9863 Å, c = 7.6217 Å and α = β = γ = 90° for 3D-IL-COF-3). The simulated PXRD patterns were in good

Table 1. Experimental and modeling results of gas adsorption on 3D-IL-COFs. BET

Pore Volume

[m2 g-1]

[mL g-1]

CO2/N2

CO2/CH4

3D-IL-COF-1

517

0.36

24.6

23.1

3D-IL-COF-2

653

0.53

24.0

22.3

3D-IL-COF-3

870

0.56

24.4

21.5

3D-COF-1a

596

0.43

7.1

5.3

3D-IL-COF-1b

537

0.40

43.6

35.1

Sample

Ideal Adsorption Selectivity

Given the high crystallinity and porosity of 3D-IL-COFs as well as the IL's good affinity to CO2, we have studied their po-



tential application in the separation of CO2. The capture and separation of CO2 as the major greenhouse gas is in the focus of energy and environmental related concerns.35 The adsorption isotherms of CO2, N2 and CH4 were measured at 298 K. As shown in Figure 3b-d, the sorption amounts of CO2 (5.34% for 3D-IL-COF-1, 7.61% for 3D-IL-COF-2 and 4.93% for 3D-ILCOF-3) are much higher than those of CH4 and N2 (0.37 and 0.35 % for 3D-IL-COF-1, 0.85 and 0.51% for 3D-IL-COF-2 and 0.33 and 0.28% for 3D-IL-COF-3 respectively), which can be attributed to the interaction between CO2 and ionic liquid. The ideal adsorption selectivity of 3D-IL-COFs was calculated from the ratio of the initial slopes in the Henry region of the isotherms.36 A significant enhancement of CO2/N2 and CO2/CH4 adsorption selectivity was observed (24.6 and 23.1 in 3D-ILCOF-1, 24.0 and 22.3 in 3D-IL-COF-2, and 24.4 and 21.5 in 3DIL-COF-3 respectively; Table 1 and Figures S21-23). Controlled experiments were also conducted by the isoreticular 3D-IL-COF-1 prepared through the solvothermal method (denoted 3D-COF-1a) and the other ionic liquid, 1-butyl-3methylimidazolium dicyanamide ([BMIm][N(CN)2], denoted 3D-IL-COF-1b, Figures S24-35). Compared with 3D-IL-COF-1, 3D-COF-1a showed a much lower adsorption selectivity for CO2/N2 (7.1) and CO2/CH4 (5.3) due to the absence of ionic liquids in its pores. Interestingly, 3D-IL-COF-1b had substantially higher adsorption selectivity for CO2/N2 (43.6) and CO2/CH4 (35.1), which further proved the IL's good affinity to CO2 (Figure 3b, Table 1 and Figures S36-37). Furthermore, preliminary breakthrough experiments for 3D-IL-COF-1 were carried out by exposing to streams containing binary mixtures of CO2/N2 or CO2/CH4 (50:50 v/v) at room temperature. The results clearly show that in both cases only CO2 is retained in the pores of 3D-IL-COF-1 while N2 and CH4 pass through without impediment (Figure 3e and 3f). This study further confirms the exceptional selectivity of IL-containing COFs to CO2. In conclusion, we have for the first time designed and synthesized a series of 3D-IL-COFs through ambient temperature and pressure ionothermal synthesis in an open system. These 3D-IL-COFs showed high crystallinity, good BET surface area, and impressive adsorption selectivity for CO2/N2 and CO2/CH4. Furthermore, 3D-IL-COFs can be prepared for very short time (e.g., three mins) and the IL can be reused without activity loss. This research not only provides a new synthetic strategy for COF materials, but also opens a potential pathway to green large-scale synthesis of COFs in industry.

ASSOCIATED CONTENT Supporting Information Synthetic procedures, SEM, FTIR, solid state 13C NMR, TGA, BET plots, and pore size distribution. This material is available free of charge via the internet at http://pubs.acs.org.

AUTHOR INFORMATION Corresponding Author *[email protected]

Notes The authors declare no competing financial interests.

ACKNOWLEDGMENT This work was supported by National Natural Science Foundation of China (21571079, 21621001, 21261130584, 21390394, 21571076, and 21571078), ″111″ project (B07016

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and B17020), Ministry of Education, Science and Technology Development Center Project (20120061130012), and the program for JLU Science and Technology Innovative Research Team. V.V. and Q.F. acknowledge the Thousand Talents program (China).

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