Construction and Application of Porous Ionic Liquids

doi:10.6023/A22010053

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (6): 848-860.DOI: 10.6023/A22010053 Previous Articles

Review

多孔离子液体的构筑及应用

李晓倩, 张靖, 苏芳芳, 王德超, 姚东东^*(), 郑亚萍^*()

西北工业大学化学与化工学院西安 710129

投稿日期:2022-01-27 发布日期:2022-07-07
通讯作者: 姚东东, 郑亚萍

作者简介:

李晓倩, 西北工业大学化学与化工学院材料学专业在读博士研究生, 研究方向为多孔离子液体的构筑及其气体吸附分离与催化转化应用.

张靖, 西北工业大学化学与化工学院在读硕士研究生, 研究方向为先进多孔液体的合成及其催化应用.

苏芳芳, 西北工业大学化学与化工学院化学专业在读博士研究生, 研究方向为先进多孔液体及无溶剂纳米流体的合成及其在光热转化领域的应用.

王德超, 西北工业大学化学与化工学院化学专业博士研究生在读, 研究方向为新型分离复合材料(无溶剂纳米流体与多孔液体及其膜材料)、碳捕集和吸附工艺、化工过程计算机模拟.

姚东东, 西北工业大学化学与化工学院副教授, 2013年获得中国科学院化学所高分子化学与物理专业博士学位, 神奈川大学博士后, 长期从事杂化多孔液体和聚合物纳米复合材料的制备及其应用研究.

郑亚萍, 西北工业大学化学与化工学院教授, 博士生导师, 美国康奈尔大学访问学者, 研究方向为多孔液体、无溶剂纳米流体的构筑及其在CO₂捕集、聚合物基复合材料纳米填料、膜分离、催化转化、光热转换等领域的应用. 现已主持完成国家自然科学基金、陕西省自然科学基金、航空科学基金等国家级、省部级纵向课题和横向课题20余项. 在AFM、ACS Nano、Angew. Chem.、Small、JMCA、CEJ、Nano-Micro Lett等权威期刊发表论文180余篇; 授权国家发明专利12件; 参编高等学校教材4部.

基金资助:
西北工业大学博士论文创新基金(CX2021110); 国家自然科学基金(21905228); 航空科学基金(2018ZF53065)

Construction and Application of Porous Ionic Liquids

Xiaoqian Li, Jing Zhang, Fangfang Su, Dechao Wang, Dongdong Yao(), Yaping Zheng()

School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi′an 710129, China

Received:2022-01-27 Published:2022-07-07
Contact: Dongdong Yao, Yaping Zheng
Supported by:
Innovation Foundation for Doctor Dissertation of NWPU(CX2021110); National Natural Science Foundation of China(21905228); Aeronautical Science Foundation of China(2018ZF53065)

The concept of porous liquids (PLs) was initially proposed and divided into three types in 2007 by James, which combine the merits of porous solids and flowing liquids. Recently, PLs have made great progress in preparations and applications. However, challenges for PLs still present to be addressed including their high density, viscosity melting temperatures, and materials cost, which severely limit their large-scale applications in flowing systems. Therefore, it is urgent to look for ideal sterically hindered solutions to construct PLs materials. Notably, the unique properties of ionic liquids (ILs), such as the tunable physicochemical properties for task-specific applications, economic, low regeneration energy requirements, enable them as promising candidates for constructing novel porous ionic liquids (PILs). Over the past five years, PILs based on ILs and existing advanced porous solids, such as porous organic cages (POCs), metal-organic frameworks (MOFs), porous carbons, zeolites, porous polymers, etc., have successively witnessed the achievement in synthesis strategies and applications. Notably, PILs exhibit remarkable properties including permanent porosity, negligible volatility, high thermal/chemical stability, non-corrosivity, adjustable melting temperature, viscosity, high gas solubilities, and fast gas diffusion, which have accelerated their applications in gas adsorption/separation, chiral separation, catalytic conversion, extraction, molecular separations, and other fields. In this review, we summarized recent research progress on the synthesis strategies, properties, and applications of PILs. In the end, challenges and future developments for PILs are summarized and prospected.

Key words: porous ionic liquids, porous liquids, ionic liquids, gas capture, separation, catalysis

Cite this article

Xiaoqian Li, Jing Zhang, Fangfang Su, Dechao Wang, Dongdong Yao, Yaping Zheng. Construction and Application of Porous Ionic Liquids[J]. Acta Chimica Sinica, 2022, 80(6): 848-860.

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Fig. & Tab. 24

Figure 1. Comparison of conventional liquids and three types of porous liquids[6]

Figure 2. (a) Two-step synthetic strategy for porous liquid fabrication, HS=hollow silica, OS=organosilane; (b) schematic representation of gas separation in membrane supported HS-liquid; (c) gas permeability obtained on (i) PEGS, (ii) HS-liquid, (iii) SS-liquid, (iv) CS-liquid, and (v) CS/Ni-liquid[23]

Figure 3. (a) Synthesis strategy for HCS-liquid; (b) modulus- temperature curve and photograph (inset) of the HCS-liquid; (c) CO2 adsorption-desorption isotherms of HCS-liquid, PEGS, SCS-liquid and PILs-PEGS composite collected below 1 MPa at 25 ℃, respectively[38]

Figure 4. Schematic illustration of the synthesis of HCS and HCS-PILs-PEGS[39]

Figure 5. (a) Synthetic procedure and chemical structure of anionic covalent cage (ACC); (b) chemical structures of 15-crown-5 and dicyclohexano-18-crown-6; (c) representation of synthetic procedures for the crown ether-ACC porous liquids[41]

Figure 6. (a) Preparation of cages 1~3; (b) cage 2 bound a range of different propanol and butanol isomers; a better shape match between guest and host cavity led to a stronger binding [42]

Figure 7. (a) Schematic synthesis of porous MOF liquid Im-UiO-PL via an ionic-exchange method; (b) the pore space in Deim-UiO-66; (c) the experimental results of catalytic conversion of CO2 with different adsorbents (black bars represent the transformed amount of CO2, red bars represent the adsorbed amount of adsorbents)[43]

Type	Sample name	Viscosity/ (Pa•s at 25 ℃)	T_m/℃	CO₂ adsorption	Ref.
PLs	PS-OS@SiNRs	Like-gel	15, 20	3.3, 4.8% (w) (0 ℃)	^[15]
	HS@OS@PEGs	6.8 at 40 ℃	20	CO₂/N₂ separation	^[23]
	HS@OS@PEGs	4.2 at 50 ℃	20	CO₂/N₂ separation
	UiO-66-liquids	14.000	–4.83	0.25 mmol•g^-1 (1 MPa 25 ℃)	^[44]
	UiO-66-liquid-M2070	4.6	–6.1	2.68 mmol•g^-1 (1 MPa 25 ℃)	^[45]
PILs	HCS-liquids	High viscosity	12	55.9% (w) (0.1 MPa)	^[38]
	100-P[VHIm]-PEGS	8.9 at 50 ℃	9.8	1.8 mmol•g^-1(0.3 MPa)	^[39]
	18-C-6-PL	—	50	0.43 mmol•g^-1(1 MPa)	^[41]

Table 1. Comparison of the viscosity, melting temperature, and CO2 adsorption capacity of type Ⅰ porous ionic liquids to coexisting traditional type Ⅰ porous liquids

Figure 8. Preparation of the crown ether cage porous liquids[46]

Figure 9. (a) Synthesis of a highly-soluble scrambled 33:133 cage mixture; (b) the 14 bulky solvents screened for both cage solubility and size-exclusion from the cage cavity; (c) scheme illustrating the size-exclusion screen for potential porous liquid solvents-each candidate solvent was added to a known xenon-loaded porous liquid (33:133 20% in PCP); (d) average xenon uptake measured by displacement from the neat solvents (1 mL, dashed lines) and from each porous liquid (200 mg 33:133 with 1 mL PCP, 20% w/V) using chloroform (1.0 molar equivalent relative to cage)-average of 3 measurements; (e) the xenon adsorption capacity of 33:133HAP and 33:133TBA at different viscosities[47]

Figure 10. (a) Schematic of preparation of MOP-18 based porous liquids; (b) the potential of mean force (PMF) between 15-crown-5 and MOP-18, and insert shows the path that 15-crown-5 approaches square windows of MOP-18; (c) the distribution density of 15-crown-5 around a single MOP-18 along X-axis and Y-axis; the high and low values are shown in yellow and blue respectively. Illustrated channels of CO2 passing through PLs-5% (w)/GO membrane (d) and 15-crown-5/GO membrane (e)[48]

Figure 11. (a) Photographs and (b) the positron lifetime traces of 15-C-5-PL collected at 25 ℃ [41]

Figure 12. Schematic illustration of the formation of ZIF-8 porous liquid[49]

Figure 13. (a) Preparation and characterization of the porous liquid; (b) identification of free volume (green regions) in simulation snapshots determined, the white regions inside the MOF are also void space, ZIF-8 and HKUST-1 with pores in PILs, then pores in Mg-MOF-74 were filled[50]

Figure 14. Depiction of the preparation strategy for the porous liquid zeolites (H-ZSM-5-liquid/[P66614][Br])[51]

Figure 15. Fabrication based on a similar compatibility principle of the MOF-based porous liquid UIO-66-liquid/[M2070][IPA] [53]

Figure 16. Illustration of synthesis strategy for ZIF-67-PILs with low viscosity[54]

Figure 17. The synthesis of ZIF-8-PILs (ZIF-8/[Bpy][NTf2])[55]

Figure 18. (a) Synthesis of the poly(ionic liquid)s (PILs, [M2070][PSS]); (b) the depiction of the preparation strategy for the HCNS-liquid[56]

Figure 19. Mechanism of CO2 absorption by a tetraalkylphosphonium acetate ionic liquid[57]

Figure 20. Illustration of synthesis strategy for COFs porous ionic liquids[59]

Figure 21. Schematic illustration of the formation of HPMo@ZIF-8-PIL[60]

Figure 22. Reaction pathway of bifunctional zeolite porous liquid (MCM-22-PL) system of the cascade deacetalization-Knoevenagel condensation[62]

Type	Sample name	Viscosity/ (Pa•s at 25 ℃)	T_m/℃	CO₂ adsorption (25 ℃)	Ref.
PLs	PL1	5.1		30.8 cm³•g^-1 (1 MPa)	^[28]
	PL4	6.0	–35	29.0 cm³•g^-1 (1 MPa)
	PL5	11.0		12.4 cm³•g^-1 (1 MPa)
	ZIF-8-g-BPEI -10	1.7	–70.1	0.98 mL•g^-1 (1 MPa)	^[27]
	ZIF-8-g-BPEI -20	7.1	–60.1	3.49 mL•g^-1 (1 MPa)	^[27]
	ZIF-8/[P66614][NTf₂]	—	—	2.12% (w) (0.5 MPa)	^[33]
PILs	ZIF-8/[DBU-PEG][NTf₂]	—	—	1.56 mmol•g^-1 (1 MPa)	^[49]
	ZIF-8/[Bpy][NTf₂]	—	—	2.5% (w)	^[50]
	H-ZSM-5-liquid	9.550	–13.5	2% (w) (1 MPa)	^[51]
	UiO-66-liquid	—	8	7.32% (w) (1 MPa)	^[52]
	ZIF-67-PLs-2	0.54		5.77 mmol•g^-1 (0.1 MPa)	^[54]
	ZIF-67-PLs-5	0.93	–67	7.12 mmol•g^-1 (0.1 MPa)
	ZIF-67-PLs-10	1.89	—	9.54 mmol•g^-1 (0.1 MPa)

Table 2. Comparison of the viscosity, melting temperature, and CO2 adsorption capacity of type Ⅲ porous ionic liquids to coexisting traditional type Ⅲ porous liquids

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	(刘文巧, 李臻, 夏春谷, 化学进展, 2018, 30, 1143.) doi: 10.7536/PC180106

多孔离子液体的构筑及应用

Construction and Application of Porous Ionic Liquids

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