Ordered porous poly(ionic liquid) crystallines: spacing confined ionic

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Ordered porous poly(ionic liquid) crystallines: spacing confined ionic surface enhancing selective CO2 capture and fixation Jingjiao Cao, Wanjian Shan, Qian Wang, Xingchen Ling, Guoqing Li, Yinong Lyu, Yu Zhou, and Jun Wang ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b19420 • Publication Date (Web): 16 Jan 2019 Downloaded from http://pubs.acs.org on January 18, 2019

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ACS Applied Materials & Interfaces

Ordered Porous Poly(ionic liquid) Crystallines: Spacing Confined Ionic Surface Enhancing Selective CO2 Capture and Fixation Jingjiao Cao†, Wanjian Shan†, Qian Wang†, Xingchen Ling†, Guoqing Li†, Yinong Lyu‡, Yu Zhou*† and Jun Wang*† †State

Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering,

Nanjing Tech University, Nanjing, Jiangsu, 210009, People’s Republic of China. ‡State

Key Laboratory of Materials-Oriented Chemical Engineering, College of Materials Science and

Engineering, Nanjing Tech University, Nanjing, Jiangsu, 210009, People’s Republic of China.

ABSTRACT: Porous poly(ionic liquid)s (PPILs) combine the features of porous materials, polymers and ionic liquids (ILs) or their derivatives, but they are normally of amorphous structure with disordered pores. Here, we report the facile synthesis of ordered porous poly(ionic liquid) crystallines (OPICs, specialized as a kind of PPILs analogues) with diverse and adjustable framework ILs moieties through Schiff base condensation of IL-derived ionic salts and neutral monomers. Ternary monomer mixtures are employed to artistically control the chemical composition and pore configurations. Compact atomic packing was achieved to give the spacing confined ionic surface with strong CO2 affinity. Through monomer control, OPICs exhibit high CO2 uptakes with excellent CO2/N2(CH4) selectivities and highly efficiently implement the CO2 fixation through catalysing epoxides cycloaddition under down to ambient conditions. 1 ACS Paragon Plus Environment

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KEYWORDS. Ordered porous materials, Porous poly(ionic liquid)s, Ionic polymer crystalline, Covalent organic frameworks, Solvothermal synthesis, Carbon dioxide capture, Carbon dioxide fixation, Cycloaddition reaction INTRODUCTION The huge numbers of organic monomers plus variable crosslinking strategies endow porous polymers with versatile chemical compositions, porosities and functionalities.1-8 Compared to disordered ones, ordered pores afford relatively uniform surface environment and special spacing confine effect.2-4 These features are of great importance for a broad spectrum of applications such as adsorption, separation and heterogeneous catalysis.8-11 However, construction of well-defined ordered porosity is challengeable for target porous polymers with highly controllable framework. One significant application of porous polymers is the capture and chemical fixation of carbon dioxide (CO2), an environmental unfavorable greenhouse gas and also an abundant, easily available C1 resource.38

CO2 adsorption and successive catalytic conversion into high value-added chemicals benefit the

sustainable chemicals production and recycling of the carbon imprinting in earth.12-17 For this purpose, selective adsorptive and catalytic active sites are required on porous polymers. Ionic liquids (ILs) and their derivatives show strong CO2 affinity and their anions (e.g., halogen, hydroxyl and carbonyl groups) are internal efficient active sites for many CO2 conversions.5,16,18-22 Therefore, porous poly(ionic liquids) (PPILs) with IL-like modules in the polymer’s skeleton are among the most attractive metal-free solid candidates for CO2 adsorption and/or conversion.20-29 Their monomers include the traditional ILs and IL derivatives such as the organic salts that are also composed of organic cations and inorganic or organic anions.20-35 In general, ionic modules from these IL-derived ionic salts have similar physiochemical properties and functions to those from traditional ILs, and these ionic salts have been employed as precursors to endow the framework ionic moieties in PPILs.20,21,31,35 Great efforts have been devoted to 2 ACS Paragon Plus Environment

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manage their chemical composition and porosity; indeed, for many functional PPILs, remarkable progress has been attained in CO2 adsorption and chemical fixation.16,20-29 However, the present PPILs are normally of amorphous structure and lack of desirable ordered porosity derived spacing confinement,24-29 which is one bottleneck to further enhance their selective adsorption and catalysis efficiency. Herein, a series of ordered PPIL crystallines (shorten as OPICs that are a kind of analogues of traditional PPILs) with the large surface area, ordered porous crystalline structure and tunable framework ionic moieties are facilely synthesized via the thermodynamically controlled Schiff base condensation of ILderived ionic salts and neutral monomers. Schiff base chemistry has been applied in the synthesis of other polymers like covalent organic frameworks (COFs).36,37 Several ionic COFs (ICOFs) were also fabricated through this method by using ionic monomers, but their structure control remains limited.38-40 For an ordered porous material, chemical composition and pore structure (surface area, pore size, atomic packing, etc.) are both crucial for adsorption and separation behavior.3-8,12,13,22 Particularly in a confined space where the host-guest interaction is sensitive to the pore diameter, the atomic packing significantly affects the surface affinity.41,42 To achieve a precise structural control, especially through the tuning of atomic packing, ternary monomer mixtures are employed in this work. By controlling the monomer mixtures, the crystalline framework of OPICs is modulated to enable strong CO2 affinity, offering high CO2 uptakes, CO2/N2(CH4) selectivities and remarkable efficiency of CO2 fixation. EXPERIMENTAL SECTION Regents. All the chemicals and reagents were commercially available and used without additional purification. 1,3,5-tris(4-aminophenyl)benzene (TAPB, 99%), p-phthaladehyde (PDA, 98%), 1,3,5benzenetricaboxaldehyde (BTCA, 95%), guanidine hydrochloride (GH, 99%), dioxane (99%), 1,3,5trimethylbenzene (97%), acetic acid (AcOH, 99.8%), tetrahydrofuran (THF, 99%), ethanol (EtOH,

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99.7%), o-dichlorobenzene (o-DCB, 99%), N-Methyl pyrrolidone (NMP, 98%), n-Butanol (n-BuOH, 99%), and methanol (MeOH, 99.5%) were purchased from Alladdin Chem.Co.. Synthetic procedure. Ordered porous poly(ionic liquid) crystallines (OPICs) and their neutral analogues were solvothermally synthesized (Scheme S1-S6). Typically, the monomers were dissolved in the solvents and heated at preset temperature for 3 days. The solid was isolated by filtration, washed with tetrahydrofuran and methanol in a Soxhlet extractor for 24 h. The powder was dried under vacuum overnight to give the corresponding products in 85~95% yields. The samples synthesized from three monomers were named as Xx%-Y-Z, in which X, Y and Z are the abbreviation of the target monomers, and x% is the X/(X+Y) molar ratio ([mole of monomer X]/[mole of monomer X and Y]). The samples synthesized from two monomers were termed Y-Z, in which Y and Z denotes the abbreviation of the target monomers. Details are in Supporting Information. Characterizations. Fourier transform infrared (FT-IR) spectra were recorded on an Agilent Cary 660 instrument. 13C cross-polarization (CP)/magic-angle-spinning (MAS) nuclear magnetic resonance (NMR) spectra were collected on a Bruker AVABCE-III spectrometer with a contact time of 2.0 ms, a recycle delay of 15.0 s and a sample spinning rate of 6 kHz. Thermogravimetric (TG) analysis was done at a heating rate of 10 K min-1 under N2 atmosphere on a STA409 instrument. CHN elemental analysis was conducted on an elemental analyzer Vario EL cube. Powder X-ray diffraction (PXRD) patterns were registered in a Rigaku Smart Lab X-ray diffractometer. Structure refinement was performed by a Le-bail method using Fullprof software. Transmission electron microscope (TEM) images were registered in a JEOL JEM-2010 (200 kV) instrument. Field emission scanning electron microscope (SEM; Hitachi S4800) was utilized to investigate the morphology. The surface chemical composition was given in X-ray photoelectron spectroscopy (XPS, AXIS UltraDLD, Japan). N2 sorption isotherms were recorded at 77 K on a BELSORP-Max analyzer. The samples were degassed at 393 K for 3 h to get a vacuum of 10-3 Torr 4 ACS Paragon Plus Environment

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before measurement. Desorption was stopped when the relatively pressure reached P/P0DB-Tp, confirming the superior potential of DB10%-Pa-Tp. CO2 adsorption capacities from breakthrough curves (Figure S49) are lower than those from single component static adsorption. The reason for this difference is attributable to that the former was carried out under dynamic condition using a gas mixture of 15% CO2 and 85% N2 at a slightly higher temperature of 308 K, whereas the latter was measured under static conditions by using CO2 at 273/298 K. High isosteric heat of CO2 adsorption (Qst) for DB10%-Pa-Tp (Figure 4h and Figures S50-52 and Table S5)43 is in accordance with its high CO2 adsorption and emphasizes the enhanced CO2 affinity within a partially ionic network. Stable recycling CO2 sorption of DB10%-Pa-Tp (Figure 4i) suggests the good ACS Paragon Plus Environment

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reusability and easy regeneration. For comparison, NC-DB-Tp, an amorphous and disordered porous counterpart of DB-Tp (Figures S53 and S54 and Table 1) exhibited inferior CO2 uptake and CO2/N2 selectivity to DB-Tp (Figures S55-59 and Tables S5 and S10). A speedy decline of Qst along with coverage (Figures S60 and S61) was observable for NC-DB-Tp, confirming that the homogeneously confined surface environment generated from the ordered porous crystalline is crucial for the superior CO2 adsorption.12 a

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Figure 5. (a) CO2 cycloaddition with epoxides. Reaction conditions: substrate (5 mmol), DB-Tp (30 mg, 0.06 mmol ionic moieties), TBAB (0.32 mol%), 323 K, 1 bar. *TBAB (1.92 mol%), 303 K. †363 K, 5 bar. (b) Recycling of DB-Tp. Epichlorohydrin (5 mmol), 323 K, 36 h. (c) CO2 cycloaddition with styrene oxide; 323 K, 72 h. (d) Activity in the absence of TBAB. Epichlorohydrin (5 mmol), 393 K, 48 h. ‡0.011 mmol ionic moieties, 96 h. Catalytic performance of selected OPICs was evaluated in the CO2 cycloaddition with epoxides, an attractive atom economic route for CO2 fixation.14-17. For DB-Tp with the highest content of ionic moieties ACS Paragon Plus Environment

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over controls, high yields (94~98%) were obtained for multiple epoxides under the mild conditions of 1 bar and 323 K (Figure 5a). After reaction, the catalyst was facilely recovered and recycled with stable activity (Figure 5b). In contrast, the activity of IL-free sample Pa-Tp, whereas the activity continuously increased along with the content of ionic moieties for DBx%-Pa-Tp series (Figure 5c). This comparison suggests that the ionic moiety in OPICs backbone serves as the active center. These conversions were aided by the commonly used additive, tetrabutylammonium bromide (TBAB), but with much lower concentration (0.32 mol%) compared with previous systems.14,16,20,22 If reasonably increasing the amount of TBAB, DB-Tp could afford a high yield of 90% in converting epichlorohydrin even under ambient conditions (Figure 5a). This is hardly reached with previous heterogeneous organocatalysts.14,16 Further, the inherent activity of DBx%-Pa-Tp series was examined in the absence of TBAB. Neat DB-Tp offered a high turnover number (TON) of 425 under atmospheric condition (Figure 5d). When we charged DB10%Pa-Tp with the equal amount of ionic moieties to DB-Tp, the former was more active than latter. Generally, the activity of a heterogeneous catalyst is affected by various parameters such as active site type and density, surface area, pore volume and particle size. Table S11 summarizes the related parameters versus the activity appeared in Figure 5c. It was observed that there is no positive relationship between yield and the surface area, pore volume, CO2 adsorption capacity or particle size, when the same catalyst dosage was used. By contrast, yield increases with raising content of ionic moiety. The reason is attributable to that the ionic moiety acts as the active site that usually plays a determining role in this reaction and higher density of active sites facilitates the reaction, whereas the other parameters do not take significant effects.16,20-22 When the comparison was made by using the same amount of active sites, DB10%-Pa-Tp exhibited slightly higher yield than DB-Tp. Previous studies indicated that the CO2 enrichment in the pores also accounted for the high activity59,60. Thus, high CO2 adsorption capability of DB10%-Pa-Tp may benefit its high catalytic activity due to this enrichment effect. Above comparisons additionally suggest that the active sites dominate the activity in this reaction while the adsorption is also responsive to the activity but plays a minor role. From this viewpoint, DB-Tp with high density of the active sites is favorable for this reaction. ACS Paragon Plus Environment

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Numerous homogeneous and heterogeneous catalysts have been developed for the CO2 cycloaddition with epoxides and heterogeneous organo-catalysts are preferred by avoiding the potential environmental problem using metal involved catalytic systems14-17,20,28,29,59-66. However, exploring a highly active, recyclable heterogeneous organocatalyst under mild conditions (e.g., low reaction temperature and atmospheric pressure) is challengeable. OPICs delivered abundant dispersive active sites within the framework of large surface area microporous channels. This structure character not only provides high density of active sites, but also facilitates the accessibility of active sites and mass transfer during the reaction. The ordered porosity benefits to create relatively homogeneous surface environment that is also advantageous for the exploiting of the catalytic performance67,68. Normally, the ordered porosity is important for the adsorption and separation and has been demonstrated by the high CO2 uptakes and excellent CO2/N2(CH4) selectivities of the fabricated OPICs. The catalysis results above indicated that the active sites, the ionic moieties, play an dominate role in the typical OPICs DBx%-Pa-Tp catalyzed CO2 cycloaddition with epoxides, while other parameters play minor roles. DB10%-Pa-Tp exhibited slightly higher yield than DB-Tp by charging the same amount of active sites, suggesting that other parameters also affect the activity. The reason was tentatively assigned to the improved adsorption capacity, which is closely related to the ordered porosity. Thus, it can be rationally that the ordered porosity would be an advantageous factor, though such improvement is not as apparent as that in the CO2 capture. Previously, high catalytic efficiency for the coupling of CO2 with epoxides relies on the task-specific introducing of metal sites or hydrogen donor functional groups into the heterogeneous catalysts14-17,20,28,29,59-65. For example, the presence of a hydrogen bond donors (HBDs) and a nucleophile led to synergistically catalysis of CO2 cycloaddition reactions16,20,69. However, despite that Tp contains phenolic moieties, the polymers are in the keto form. The residual phenolic moieties coming from the unreacted terminal ones should be in a much low level. Therefore, the influence of residual phenolic moieties can be rationally negligible, as demonstrated by the low activity of Pa-Tp. In a rough comparison, DBx%-Pa-Tp presented at least comparably high efficiency under mild conditions. For example, excessive additives were usually employed in many catalytic systems14,16,20,22, whereas DBx%-Pa-Tp gave high yield in the presence of ACS Paragon Plus Environment

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small amount of additive, as mentioned above. Considering that the ionic moieties of DBx%-Pa-Tp have no promotion groups but provide comparable catalytic efficiency to those catalytically task-specific multifunctional PPILs and other catalysts,16,20,28,29 the catalytic potentiality of OPICs in CO2 fixation is attractive in the future. CONCLUSION In conclusion, structure controllable OPICs are solvothermally synthesized through Schiff base condensation of IL-derived ionic salts and neutral monomers. Ternary monomer mixtures enable finely manipulating of chemical composition and pore configuration to afford strong CO2 affinity for efficient selective CO2 capture. The catalytic functions of ionic moieties transform these OPICs into active recyclable heterogeneous organocatalysts for CO2 fixation. These findings highlight the prospects of ordered porous poly(ionic liquid) crystallines potentially important for gas storage, separation and catalysis.

ASSOCIATED CONTENT Supporting Information. The following files are available free of charge. Details of synthetic procedures, FTIR, 13C NMR, XPS, TG, PXRD, SEM, TEM, nitrogen sorption isotherm, pore size distribution, CO2, N2 and CH4 sorption behavior. (PDF) AUTHOR INFORMATION Corresponding Author * [email protected] (Y. Zhou) * [email protected] (J. Wang) ACS Paragon Plus Environment

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ORCID Yu Zhou: 0000-0003-1757-3705 Jun Wang: 0000-0002-7669-9992 Notes The authors declare no competing financial interests. ACKNOWLEDGMENT This work was supported by the National Natural Science Foundation of China (Grant Nos. U1662107, 21476109, 21303084, and 21136005), and the Project of Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). REFERENCES (1)

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Ordered porous poly(ionic liquid) crystallines: spacing confined ionic

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