Tuning the Capture of CO2 Through Entropic Effect Induced by

Subscriber access provided by UNIV OF SOUTHERN INDIANA

Chemical and Dynamical Processes in Solution; Polymers, Glasses, and Soft Matter

Tuning the Capture of CO2 Through Entropic Effect Induced by Reversible Trans-cis Isomerization of Light-responsive Ionic Liquids Wenjun Lin, Mingguang Pan, Qiaoxin Xiao, Haoran Li, and Congmin Wang J. Phys. Chem. Lett., Just Accepted Manuscript • DOI: 10.1021/acs.jpclett.9b01023 • Publication Date (Web): 31 May 2019 Downloaded from http://pubs.acs.org on June 1, 2019

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

The Journal of Physical Chemistry Letters

Tuning the Capture of CO2 through Entropic Effect Induced by Reversible Trans−Cis Isomerization of Light-Responsive Ionic Liquids Wenjun Lin,† Mingguang Pan,† Qiaoxin, Xiao, Haoran Li, and Congmin Wang* Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou 310027, China. AUTHOR INFORMATION Corresponding Author [email protected].

ACS Paragon Plus Environment

1

The Journal of Physical Chemistry Letters 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 2 of 20

ABSTRACT: Despite a great deal of gas capture strategies based on ionic liquids, reversible tuning of gas absorption by pure ionic liquids using light irradiation has never been reported. Herein, we demonstrate a novel strategy for tuning the capture of CO2 by light-responsive ionic liquids through reversible trans−cis isomerization. These light-responsive ionic liquids were constructed by tailoring the azobenzene group to the cationic moiety, which exhibited different CO2 absorption ability before and after UV irradiation. Through a combination of absorption experiments, NMR spectroscopy, DSC analysis, viscosity measurement and quantum chemical calculations, the results indicated that the significant difference in CO2 absorption capacity originated from the entropic effect, which was induced by the change in the aggregation state during trans−cis isomerization. This reversible isomerization of ionic liquids upon alternating irradiation of UV light and blue light showed the potential to switch the capture and release of CO2 in an energy−saving way.


2

Page 3 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


TOC GRAPHICS


3


Page 4 of 20

As a consequence of global warming and climate change triggered by the rising concentration of CO2 in the atmosphere, a significant challenge in carbon capture and storage was to develop promising strategies or excellent materials for efficient, reversible, and economical CO2 uptake.17

Ionic liquids (ILs) exhibited great promise as absorbents for CO2 absorption in view of their

overwhelming advantages including negligible vapor pressure, high thermal stability, excellent CO2 solubility, and designable nature.8-17 Notably, the Davis group pioneered the first example of chemisorption of CO2 by incorporating the amine group onto the cation in 2002.18 Inspired by this work, a great deal of reports on the functionalization of ILs were emerged and developed for tuning CO2 capture including uptake capacity,19-23 absorption kinetics,24-27 and desorption energy.28-31 However, current absorption technologies based on ILs always relied on enthalpy swings, and consumed a huge amount of energy for regeneration. In this regard, it was highly desired to put forward novel strategies that did not require extra vaccum or heating for triggering CO2 release. Stimuli−responsive materials, which were structurally switchable by external stimuli such as heat, pH, light, enzyme, mechanical force, etc. had particularly important applications including sol−gel transition, shape memory, drug delivery and release, self−assembly, and advanced devices.32-37 They provided the potential to accomplish dynamic and reversible alteration of gas absorption. Among these stimuli, light, as an abundant and non-invasive energy resource, has been widely projected onto a specific position of the target in a clean, fast, and accurate way. Given that the renewable light triggers the reversible CO2 capture and release through altering the conformation of light−responsive materials, it may be possible to reduce the energy expenditure for regeneration. For example, porous solid materials such as metal-organic framework (MOF) containing azobenzene groups could reversibly switch the captured amount of CO2 through morphology variation of framework induced by the photo-isomerization of azobenzene units.38-43


4

Page 5 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


However, to the best of our knowledge, there are no examples for photo−switching capture of CO2 through strong chemical interaction up to now, especially by ILs.44-45 It was well known that azobenzene group was one of the most popular light−responsive units because of its robust, rapid, and reversible photoisomerization.46 Therefore, light−responsive ILs were constructed by incorporating the azobenzene unit to the cationic moiety. Upon irradiation with UV and visible light, the azobenzene group would undergo reversible trans−cis isomerization and accordingly led to the change of physicochemical properties including geometry, viscosity, polarity, etc. Our strategy was that if the conformation of the azobenzene group changed upon irradiation of light, the charge distribution, aggregation state, and so on of the ILs maybe accordingly varied, which would lead to some variations in absorption performance of CO2. This alteration of CO2 capacity could be confirmed by experimental absorption and

13

C NMR

spectroscopy. The difference in CO2 uptake between trans and cis IL would be explained through a combination of quantum chemical calculations, viscosity measurement, and NOSEY spectroscopy, indicating the importance of the entropy, which was induced by the change in the aggregation state during trans−cis isomerization. Moreover, the reversible isomerization of ILs could be directly achieved by alternating irradiation of UV light and blue light on the thin film of the ILs, indicating the potential in light-induced release of CO2. Light responsive ILs were prepared via introducing an azobenzene group into the phosphonium cation, where triazole was used as the anion, which was shown in Scheme 1. For example, in the preparation of typical IL trans−azoILa, azobenzene−containing cation was firstly constructed in a yield of 92% from the salfication of tributylphosphine and bromoazobenzene 1a, where 1a was obtained through a reaction between 4−phenylazophenol, 1,4−dibromobutane and K2CO3. Then, trans−azoILa was obtained by the neutralization of triazole with an ethanol solution of 3a in a


5


Page 6 of 20

quantitative yield, while 3a was afforded through the anion−exchange method from 2a. In order to discuss the effect of the cation, two other kinds of ILs with different chain or substituted azobenzene were also prepared. Structures of these light−responsive ILs were verified by 1H NMR, 13

C NMR and Mass spectroscopy (Supporting Information Fig. S1-S15).

Scheme 1. Structure of light-responsive ionic liquids. The reversible light−isomerization about the azo bond between trans and cis states upon light irradiation was monitored by UV-vis spectroscopy (Figure 1). The fresh sample of azoILa in tetrahydrofuran (THF) solution was primarily in trans form, which exhibited a typical π–π* band around 349 nm and a n–π* absorption peak at 443 nm. After UV (365 nm) irradiation, the intensity of the 349 nm band decreased remarkably and the 443 nm band increased slightly, along with a naked−eye color variation (Figure 1a), indicated the trans to cis transformation. On the contrary, upon further blue light irradiation, the π–π* absorption increased with a slight decrease in the n– π* absorption.


6

Page 7 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Figure 1. (a) UV–vis spectra of trans–azoILa solution (5.0 × 10-5 mol·L-1 in THF) before (I) and after (II) irradiation of UV light, and after (III) further irradiation of blue light. Herein, II and III are the photostationary state. Inset: Colour change of trans-azoILa solution (1.0 mM in THF). (b) Changes in absorbance at 349 nm of trans-azoILa solution through alternating irradiation with UV and blue light as determined by UV method. Moreover, the cis to trans isomerization of the IL was also investigated by differential scanning calorimetry (DSC). Upon heating cis-azoILa or cis-azoILb, the broad exothermic peak appeared around at 52°C with the enthalpy variation (ΔH) values of 48.2 kJ·mol-1 or 52.6 kJ·mol-1 for the pure cis isomer (Figure S16), respectively. The observed changes in enthalpy ΔH, associated with the thermally induced cis–trans isomerization of the ILs, was in agreement with the reported energy (ΔHcis−trans, about 50 kJ·mol-1) stored in a cis–azobenzene chromophore.47-48 The effect of isomerization of light–responsive ILs on CO2 absorption was investigated, which was shown in Table 1. It was seen that the trans-azoILs could capture an equimolar amount of CO2 (20°C, 1 bar), which was in accordance with the results by quantitative 13C NMR spectroscopy


7


Page 8 of 20

and TGA analysis (Figure S17-20). For example, as shown in Table 1, molar ratio of CO2 to transazoILb to CO2 is 0.92, while CO2 capacity determined by

13

C NMR method is 0.90 mol·mol-1

(Figure S18). However, after treating with UV irradiation, CO2 capacity of cis–azoILs such as cis–azoILb decreased dramatically from the original 0.92 mol·mol-1 to 0.63 mol mol-1. It was worthy to note that the CO2 capture process by cis–azoILs was conducted in the dark, so the light– induced geometry transformation almost did not occur (a slight decrease of the cis content from 87 mol% to 85 mol%). Under heating at 80°C and N2 purge, the cis–azoILb–CO2 complex was allowed to return to the trans–azoILb, where CO2 capacity was returned to 0.89 mol·mol-1 at 20 °C and 1 bar (Figure 2). In order to understand the decreased uptake of CO2 when the IL converted from the trans to cis state, the effect of the cis molar content of the IL on CO2 absorption capacity was investigated in detail (Figure 2). Clearly, the absorption capacity of CO2 reduced when the cis content of the IL increased. With the aid of quantitative 13C NMR spectra, the chemical interaction between the IL and CO2 could be easily quantified. As revealed in Figure 3, the chemisorbed CO2 appeared at around 160.0 ppm. The chemisorption capacity of trans-IL such as trans-azoILb was 0.90 mol·mol1

, while it changed to 0.69 mol·mol-1 when the cis content in azoILb–CO2 increased to 68 mol%,

which was consistent with the CO2 absorption data. As the scanning process for quantitative 13C NMR study was time-consuming, where it needed 14 hours to finish the measurement, it was reasonable that the cis content decreased a little from the original 68 mol% to 65 mol%, even the measurement was in the dark at 20 °C.


8

Page 9 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Table 1. The effect of trans−cis isomerization on absorption capacity, viscosity, and ΔHcis−trans by light-responsive ionic liquids. Ionic liquid

Absorption Viscosity[b] capacity[a]

trans-azoILa

0.90

220700

cis-azoILa[d]

0.62

14630

trans-azoILb

0.92

62800

cis-azoILb[d]

0.63

2110

trans-azoILc

0.95

53200

cis-azoILc[d]

0.76

5350

ΔHcis– [c] trans

41.0

45.5

35.0

[a] CO2 absorbed at 20 oC and 1 bar, mole CO2 per mole IL. [b] Determined at 25 oC, cP. [c] The observed changes in enthalpy (ΔH) through the cis to trans isomerization were recorded by DSC analysis (the cis contents for cis-azoILa, cis-azoILb and cis-azoILc were 85 mol%, 87 mol%, and 88 mol%, respectively). [d] After CO2 absorption, the molar cis content was determined by 1H NMR spectroscopy (cis-azoILa-CO2, 82.5 mol%; cis-azoILb-CO2, 85 mol%; cis-azoILc-CO2, 87%).

Figure 2. Effect of the cis molar content of azoILb on CO2 absorption capacity. Here, the red refers to trans IL, which underwent trans−cis−trans isomerization by UV irradiation and heating. The cis content was determined by 1H NMR spectroscopy after CO2 absorption.


9


Page 10 of 20

Figure 3. Quantitative 13C NMR spectra (150 MHz, 20 oC) of azoILb after the uptake of CO2: (a) trans-azoILb-CO2, 0.90 mol·mol-1 IL; (b) cis-azoILb-CO2, 0.69 mol·mol-1 IL. The cis content in cis-azoILb-CO2 reduced from the original 68 mol% to 65 mol% due to the time-consuming scanning process of quantitative

13

C NMR spectra. ο, trans-isomer; *, cis-isomer. Inset: the

enlarged view of chemical shift at around 146.0 ppm. Obviously, there was a significant difference between trans IL and cis IL in CO2 absorption, which was superior to typical photochromic MOF (Table S2). We believed that it was related to the conformation transformation of the azobenzene during trans–cis isomerization, leading to the variation in CO2 absorption enthalpy or absorption entropy. Which one played the dominant role? Firstly, quantum chemical calculations were carried out to understand the significant difference in CO2 capacity by these light-responsive IL at B3LYP/6-31G++(d, p) level. As shown in Figure 4a and 4b, the natural bond orbital charge (NBO) distributions of the trans-azoILb and cis-azoILb were very close. For instance, the NBO charges of the N atoms on 1, 2, 4-triazole anion in transazoILb were -0.573, -0.468 and -0.468, respectively, while those in cis-azoILb were -0.573, -0.468 and -0.467, respectively, which indicated the interaction between trans-azoILb or cis-azoILb and CO2 was similar. Moreover, the effect of trans–cis isomerization on CO2 absorption enthalpies by these light-responsive ILs was also investigated, which was shown in Figure 4c and 4d. It can be


10

Page 11 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


seen that CO2 absorption enthalpies by trans-azoILb and cis-azoILb were -40.4 and -40.8 KJ·mol1

, respectively. These calculated results indicated CO2 absorption enthalpy was not the key factor

led to different absorption capacity. In order to verify quantum chemical calculations results, the effect of the temperature on CO2 absorption capacity by trans-azoILb or cis-azoILb were determined, which was shown in Table S1 and Figure S21. On the basis of relationship between CO2 absorption capacity and the temperature, experimental absorption enthalpy and absorption entropy by trans-azoILb or cisazoILb could be obtained via van’t Hoff equation. It was seen in Table 2 that experimental enthalpies ΔH of trans-azoILb and cis-azoILb with CO2 were -43.9 and -44.6 kJ·mol-1, respectively. Therefore, the effect of trans-cis isomerization on experimental absorption enthalpy was weak, which was in agreement with the calculated results. These evidences indicated that enthalpy change was not the main reason for the difference in CO2 absorption, where the entropy change was the key for different CO2 absorption capacity (Table 2). Table 2. The effect of trans-cis isomerization on NBO charge of the N atom in the anion, CO2 absorption Gibbs free energy, absorption enthalpies and absorption entropies by light-responsive ILs. Ionic liquids

trans-azoILb

cis-azoILb

NBO charge of N atom in the anion [a]

-0.468, -0.468, -0.573

-0.468, -0.467, -0.573

∆G (KJ·mol-1) [b]

-5.9

-3.4

∆H (KJ·mol-1)[c]

-43.9

-44.6

∆S (J·mol-1·K-1)[c]

-129

-140


11


Page 12 of 20

[a]. The NBO charge of N in the anion was obtained at the B3LYP/6-31++G(d, p) level. [b]. The Gibbs free energy was calculated by ΔG= -RTlnK at 293.15K using the 1:1 reaction model. [c]. The enthalpy and entropy were obtained using the van’t Hoff equation (Figures S21).

Figure 4. Quantum chemical calculations results. NBO charge distributions of (a) trans-azoILb and (b) cis-azoILb. NBO charge distributions of (c) trans-azoILb with CO2, absorption enthalpy ΔH= -40.4 kJ·mol-1 and (d) cis-azoILb with CO2, absorption enthalpy ΔH= -40.8 kJ·mol-1. It was known that the entropy was often related to the spatial configuration of molecules. During the isomerization of light-responsive IL, its spatial configuration varied significantly, leading to some distinct change in physical property such as viscosity. Therefore, the viscosity of these light-responsive ILs before and after irradiation was determined. It was seen in Table 1 that the viscosity of the IL such as azoILb decreased significantly from 62800 cP to 2110 cP during


12

Page 13 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


trans-to-cis isomerization, indicating the remarkable change of aggregation state of the IL, which led to the difference in CO2 absorption entropy.49-51 The difference in aggregation state between trans-azoILb and cis-azoILb was also investigated through NOESY spectroscopy, which was shown in Figure S22. It was seen in Figure S22a that the NOESY spectrum of trans-azoILb exhibited cross signals between H1, H2, H3, H4 and H5 of different azobenzene moieties, indicating its strong aggregation interaction, which was agreeable with its high viscosity. However, for cis-azoILb, the NOESY spectrum (Figure S22b) did not show such signals. Furthermore, the NOESY spectra of trans-azoILb and cis-azoILb after the absorption of CO2 were measured, which were shown in Figure S22c and S22d. As seen, the aggregation state also existed after CO2 absorption for trans-azoILb, but did not occur for cisazoILb. In order to further verify the significant effect of aggregation state change of the IL on CO 2 capacity, a kind of new light-responsive IL azoILc was designed and prepared to reduce the change of the aggregation state, because the incorporation of methyl group on the cation would make the azobenzene group twist. As shown in Table 1, the change of viscosity from cis to trans state by azoILc was 9.9 folds, and the enthalpy variation (ΔH) was 40.2 kJ·mol-1. Compared with transazoILb, the smaller change of viscosity and enthalpy for azoILc during trans–cis isomerization indicated the reduced change of the aggregation state. As expected, the gap of absorption capacity of CO2 for the trans-azoILc and cis-azoILc was only 0.19 mol·mol-1, lower than that for azoILb with a value of 0.29 mol·mol-1. Therefore, we believed that the entropic effect was caused by the varied aggregation state of the IL via light-induced geometry change, leading to a significant difference in CO2 absorption capacity.


13


Page 14 of 20

Moreover, the effect of the isomerization of light-responsive IL on absorption rate was also significant, which was shown in Figure S23. It can be seen that the cis-azoILb had a faster absorption kinetics of CO2 than the trans-azoILb. The improved absorption rate was as a result of a dramatic decrease of viscosity through trans-to-cis transformation after UV irradiation. Generally, the presence of hydrogen bonds determined the absorption kinetics of CO2 in amino-functionalized ILs.49-55 Different from the previous strategies, this work indicated that the viscosity of the IL also could be tuned through light-induced geometric change, leading to different uptake rate of CO2. Considering that the cis state of IL was obtained through the evaporation of photo–irradiated solution, where the removal of THF solvent needed additional energy, we further developed a nonsolvent method to obtain the cis–IL by direct irradiation on the thin film of trans-IL with UV light (Figure S24). As revealed by 1H NMR spectra, irradiation on the film of trans–azoILb by UV light for 2 hours yielded near 77 mol% cis content, and the cis content decreased to 18 mol% after further irradiation by blue light for 2 hours (Figure S24a). The reversible photo-isomerization process (Figure S24b) could be recycled more than 5 times as indicated by the isomerization ratio, indicating that the potential of light-responsive ILs to switch absorption capacity of CO2 by light irradiation (Figure S25-26). In conclusion, we gave the first example of tuning CO2 capture of ILs by light-irradiation. Our results indicated that trans-azoIL and cis-azoIL had a different absorption performance of CO2. After UV irradiation on the light-respective IL, the uptake of CO2 reduced significantly. Through a combination absorption experiments, quantitative

13

C NMR, quantum chemical calculations,

viscosity measurement, and NOESY spectrum, the results indicated that the significant difference in CO2 capacity originated from the entropic effect induced by the varied aggregation state through


14

Page 15 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


trans-to-cis transformation. This work provided a new way to employ renewable energy such as light to achieve efficient capture and release of gas by IL.

ASSOCIATED CONTENT Supporting Information Experimental and structure characterization; Figure S1-S26; Table S1; This material is available free of charge via the Internet at http://pubs.acs.org AUTHOR INFORMATION Corresponding Author [email protected]. Author Contributions †These authors contributed equally to this work. Notes The authors declare no competing financial interests. ACKNOWLEDGMENT We acknowledge the support of the National Key Basic Research Program of China (2015CB251401), Zhejiang Provincial Natural Science Foundation of China (LZ17B060001), National Natural Science Foundation of China (No.21776239), and the Fundamental Research Funds of the Central Universities. REFERENCES


15


Page 16 of 20

(1) McCann, N.; Maeder, M.; Attalla, M. Simulation of Enthalpy and Capacity of CO2 Absorption by Aqueous Amine Systems. Ind. Eng. Chem. Res. 2008, 47, 2002-2009. (2) Rochelle, G. T. Amine Scrubbing for CO2 Capture. Science. 2009, 325, 1652-1654. (3) Hicks, J. C.; Drese, J. H.; Fauth, D. J.; Gray, M. L.; Qi, G.; Jones, C. W. Designing Adsorbents for CO(2) Capture from Flue Gas-Hyperbranched Aminosilicas Capable of capturing CO(2) reversibly. J. Am. Chem. Soc. 2008, 130, 2902-2903. (4) D'Alessandro, D. M.; Smit, B.; Long, J. R. Carbon Dioxide Capture: Prospects for New Materials. Angew. Chem. Int. Ed. 2010, 49, 6058-6082. (5) Zhang, J.; Chai, S.; Qiao, Z.; Mahurin, S.; Chen, J.; Fang, Y.; Wan, S.; Nelson, K.; Zhang, P.; Dai, S. Porous Liquids: A Promising Class of Media for Gas Separation. Angew. Chem. Int. Ed. 2015, 54, 932-936. (6) Chen, K. H.; Shi, G. L.; Zhang, W. D.; Li, H. R.; Wang, C. M. Computer-Assisted Design of Ionic Liquids for Efficient Synthesis of 3(2H)-Furanones: A Domino Reaction Triggered by CO2. J. Am. Chem. Soc. 2016, 138, 14198-14201. (7) Macfarlane, D. R.; Forsyth, M.; Holett, P. C.; Pringle, J. M.; Sun, J.; Annat, G.; Neil, W.; Lzgorodina, E. I. Ionic Liquids in Electrochemical Devices and Processes: Managing Interfacial Electrochemistry. Acc. Chem. Rec. 2007, 40, 1165-1173. (8) Wilkes, J. S.; Zaworotko, M. J. Air and Water Stable 1-Ethyl-3-Methylimidazolium Based Ionic Liquids. J. Chem. Soc. Chem. Commun. 1992, 965-967. (9) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic Liquid (Molten Salt) Phase Organometallic Catalysis. Chem. Rev. 2002, 102, 3667-3691. (10) Blanchard, L. A.; Hancu, D.; Beckman, E. J.; Brennecke, J. F. Green Processing using Ionic Liquids and CO2. Nature. 1999, 399, 28-29. (11) Wasserscheid, P.; Keim, W. Ionic Liquids - New "Solutions" for Transition Metal Catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772-3789. (12) Huang, J. F.; Luo, H.; Liang, C.; Sun, I. W.; Baker, G. A.; Dai, S. Hydrophobic Bronsted Acid-Base Ionic Liquids Based on PAMAM Dendrimers with High Proton Conductivity and Blue Photoluminescence. J. Am. Chem. Soc. 2005, 127, 12784-12785. (13) Lee, J. S.; Wang, X.; Luo, H.; Baker, G. A.; Dai, S. Facile Ionothermal Synthesis of Microporous and Mesoporous Carbons from Task Specific Ionic Liquids. J. Am. Chem. Soc. 2009, 131, 4596-4597.


16

Page 17 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(14) Cadena, C.; Anthony, J. L.; Shah, J. K.; Morrow, T. I.; Brennecke, J. F.; Maginn, E. J. Why is CO2 So Soluble in Imidazolium-Based Ionic Liquids?. J. Am. Chem. Soc. 2004, 126, 53005308. (15) Bara, J. E.; Camper, D. E.; Gin, D. L.; Noble, R. D. Room-Temperature Ionic Liquids and Composite Materials: Platform Technologies for CO2 Capture. Acc. Chem. Res. 2010, 43, 152-159. (16) MacFarlane, D. R.; Tachikawa, N.; Forsyth, M.; Pringle, J. M.; Howlett, P. C.; Elliott, G. D.; Davis, J. H.; Watanabe, M.; Simon, P.; Angell, C. A. Energy Applications of Ionic Liquids. Energy. Environ. Sci. 2014, 7, 232-250. (17) Smiglak, M.; Pringle, J. M.; Lu, X.; Han, L.; Zhang, S.; Gao, H.; MacFarlane, D. R.; Rogers, R. D. Ionic Liquids for Energy, Materials, and Medicine. Chem. Commun. 2014, 50, 92289250. (18) Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H. CO2 Capture by A Task-Specific Ionic Liquid. J. Am. Chem. Soc. 2002, 124, 926-927. (19) Gurkan, B. E.; de la Fuente, J. C.; Mindrup, E. M.; Ficke, L. E.; Goodrich, B. F.; Price, E. A.; Schneider, W. F.; Brennecke, J. F. Equimolar CO2 Absorption by Anion-Functionalized Ionic Liquids. J. Am. Chem. Soc. 2010, 132, 2116-2117. (20) Saravanamurugan, S.; Kunov-Kruse, A. J.; Fehrmann, R.; Riisager, A. Amine-Functionalized Amino Acid Based Ionic Liquids as Efficient and High Capacity Absorbents for CO2. ChemSusChem. 2014, 7, 897-902. (21) Luo, X.; Guo, Y.; Ding, F.; Zhao, H.; Cui, G.; Li, H.; Wang, C. Significant Improvements in CO2 Capture by Pyridine-Containing Anion-Functionalized Ionic Liquids through MultipleSite Cooperative Interactions. Angew. Chem. Int. Ed. 2014, 53, 7053-7057. (22) Vijayraghavan, R.; Pas, S. J.; Izgorodina, E. I.; MacFarlane, D. R. Diamino Protic Ionic Liquids for CO2 Capture. Phys. Chem. Chem. Phys. 2013, 15, 19994-19999. (23) Chen, F. F.; Juang, K.; Zhou, Y.; Tian, Z. Q.; Zhu, X.; Tao, D. J.; Jiang, D.; Dai, S. MultiMolar Absorption of CO2 by the Activation of Carboxylate Groups in Amino Acid Ionic Liquids. Angew. Chem. Int. Ed. 2016, 55, 7166-7170. (24) Gutowski, K. E.; Maginn, E. J. Amine-Functionalized Task-Specific Ionic Liquids: A Mechanistic Explanation for the Dramatic Increase in Viscosity upon Complexation with CO2 from Molecular Simulation. J. Am. Chem. Soc. 2008, 130, 14690-14704.


17


Page 18 of 20

(25) Camper, D.; Bara, J. E.; Gin, D. L.; Noble, R. D. Room-Temperature Ionic Liquid-Amine Solutions: Tunable Solvents for Efficient and Reversible Capture of CO2. Ind. Eng. Chem. Res. 2008, 47, 8496-8498. (26) Li, X.; Hou, M.; Zhang, Z.; Han, B.; Yang, G.; Wang, X.; Zou, L. Absorption of CO2 by Ionic Liquid/Polyethylene Glycol Mixture and the Thermodynamic Parameters. Green Chem. 2008, 10, 879-884. (27) Zhang, J.; Zhang, S.; Dong, K.; Zhang, Y.; Shen, Y.; Lv, X. Supported Absorption of CO2 by Tetrabutylphosphonium Amino Acid Ionic Liquids. Chem. Eur. J. 2006, 12, 4021-4026. (28) Wang, C.; Luo, X.; Luo, H.; Jiang, D. E.; Li, H.; Dai, S. Tuning the Basicity of Ionic Liquids for Equimolar CO2 Capture. Angew. Chem. Int. Ed. 2011, 50, 4918-4922. (29) Simons, T. J.; Verheyen, T.; Izgorodina, E. I.; Vijayaraghavan, R.; Young, S.; Pearson, A. K.; Pas, S. J.; MacFarlane, D. R. Mechanisms of Low Temperature Capture and Regeneration of CO2 Using Diamino Protic Ionic Liquids. Phys. Chem. Chem. Phys. 2016, 18, 1140-1149. (30) Gurkan, B.; Goodrich, B. F.; Mindrup, E. M.; Ficke, L. E.; Massel, M.; Seo, S.; Senftle, T. P.; Wu, H.; Glaser, M. F.; Shah, J. K.; Maginn, E. J.; Brennecke, J. F.; Schneider, W. F. Molecular Design of High Capacity, Low Viscosity, Chemically Tunable Ionic Liquids for CO2 Capture. J. Phys. Chem. Lett. 2010, 1, 3494-3499. (31) Seo, S.; Simoni, L. D.; Ma, M.; DeSilva, M. A.; Huang, Y.; Stadtherr, M. A.; Brennecke, J. F. Phase-Change Ionic Liquids for Postcombustion CO2 Capture. Energy Fuels. 2014, 28, 5968-5977. (32) Stuart, M. A.; Huck, W. T.; Genzer, J.; Muller, M.; Ober, C.; Stamm, M.; Sukhorukov, G. B.; Szleifer, I.; Tsukruk, V. V.; Urban, M.; Winnik, F.; Zauscher, S.; Luzinov, I.; Minko, S. Emerging Applications of Stimuli-Responsive Polymer Materials. Nat. Mater. 2010, 9, 101113. (33) Giri, S.; Trewyn, B. G.; Stellmaker, M. P.; Lin, V. S. Y. Stimuli-Responsive ControlledRelease Delivery System Based on Mesoporous Silica Nanorods Capped with Magnetic Nanoparticles. Angew. Chem. Int. Ed. 2005, 44, 5038-5044. (34) Jin, H.; Zheng, Y.; Liu, Y.; Cheng, H.; Zhou, Y.; Yan, D. Reversible and Large-Scale Cytomimetic Vesicle Aggregation: Light-Responsive Host-Guest Interactions. Angew. Chem. Int. Ed. 2011, 50, 10352-10356.


18

Page 19 of 20 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(35) Dong, R.; Zhu, B.; Zhou, Y.; Yan, D.; Zhu, X. "Breathing" Vesicles with Jellyfish-Like OnOff Switchable Fluorescence Behavior. Angew. Chem. Int. Ed. 2012, 51, 11633-11637. (36) Liu, Y.; Yu, C.; Jin, H.; Jiang, B.; Zhu, X.; Zhou, Y.; Lu, Z.; Yan, D. A Supramolecular Janus Hyperbranched Polymer and its Photoresponsive Self-Assembly of Vesicles with Narrow Size Distribution. J. Am. Chem. Soc. 2013, 135, 4765-4770. (37) Jiang, W.; Zhou, Y.; Yan, D. Hyperbranched Polymer Vesicles: from Self-Assembly, Characterization, Mechanisms, and Properties to Applications. Chem. Soc. Rev. 2015, 44, 3874-3889. (38) Baroncini, M.; d'Agostino, S.; Bergamini, G.; Ceroni, P.; Comotti, A.; Sozzani, P.; Bassanetti, I.; Grepioni, F.; Hernandez, T. M.; Silvi, S.; Venturi, M.; Credi, A. Photoinduced Reversible Switching of Porosity in Molecular Crystals Based on Star-Shaped Azobenzene Tetramers. Nat. Chem. 2015, 7, 634-640. (39) Park, J.; Yuan, D.; Pham, K. T.; Li, J. R.; Yakovenko, A.; Zhou, H. C. Reversible Alteration of CO2 Adsorption upon Photochemical or Thermal Treatment in a Metal-Organic Framework. J. Am. Chem. Soc. 2012, 134, 99-102. (40) Lyndon, R.; Konstas, K.; Ladewig, B. P.; Southon, P. D.; Kepert, P. C. J.; Hill, M. R. Dynamic Photo-Switching in Metal Organic Frameworks as a Route to Low-Energy Carbon Dioxide Capture and Release. Angew. Chem. Int. Ed. 2013, 52, 3695-3698. (41) Luo, F.; Fan, C. B.; Luo, M. B.; Wu, X. L.; Zhu, Y.; Pu, S. Z.; Xu, W. Y.; Guo, G. C. Photoswitching CO2 Capture and Release in a Photochromic Diarylethene Metal-Organic Framework. Angew. Chem. Int. Ed. 2014, 53, 9298-9301. (42) Huang, R. H.; Hill, M. R.; Babarao, R.; Medhekar, N. V. CO2 Adsorption in Azobenzene Functionalized Stimuli Responsive Metal-Organic Frameworks. J. Phys. Chem. C. 2016, 120, 16658–16667. (43) Knebel, A.; Sundermann, L.; Mohmeyer, A.; Strauss, I.; Friebe, S.; Behrens, P.; Caro, J. Azobenzene Guest Molecules as Light-Switchable CO2 Valves in an Ultrathin UiO-67 Membrane. Chem. Mater. 2017, 29, 3111−3117. (44) Zhang, S.; Liu, S.; Zhang, Q.; Deng, Y. Solvent-Dependent Photoresponsive Conductivity of Azobenzene-Appended Ionic Liquids. Chem. Commun. 2011, 47, 6641-6643. (45) Branco, L. C.; Pina, F. Intrinsically Photochromic Ionic Liquids. Chem. Commun. 2009, 62046206.


19


Page 20 of 20

(46) Szymanski, W.; Beierle, J. M.; Kistemaker, H. A.; Velema, W. A.; Feringa, B. L. Reversible Photocontrol of Biological Systems by the Incorporation of Molecular Photoswitches. Chem. Rev. 2013, 113, 6114-6178. (47) Gur, I.; Sawyer, K.; Prasher, R. Searching for a Better Thermal Battery. Science. 2012, 335, 1454-1455. (48) Ishiba, K.; Morikawa, M. A.; Chikara, C.; Yamada, T.; Iwase, K.; Kawakita, M.; Kimizuka, N. Photoliquefiable Ionic Crystals: A Phase Crossover Approach for Photon Energy Storage Materials with Functional Multiplicity. Angew. Chem. Int. Ed. 2015, 54, 1532-1536. (49) Pan, M G.; Cao, N. N.; Lin, W. J.; Lou, X. Y.; Chen, K. H.; Che, S. Y.; Li, H. R.; Wang, C. M. Reversible CO2 Capture by Conjugated Ionic Liquids through Dynamic Covalent CarbonOxygen Bonds. ChemSusChem. 2016, 9, 2351-2357. (50) Luo, X. Y.; Ding, F.; Lin, W. J.; Qi, Y. Q.; Li, H. R.; Wang, C. M. Efficient and EnergySaving CO2 Capture through the Entropic Effect Induced by the Intermolecular Hydrogen Bonding in Anion-Functionalized Ionic Liquids. J. Phys. Chem. Lett. 2014, 5, 381-386. (51) Luo, X. Y.; Fan, X.; Shi, G. L.; Li, H. R.; Wang, C. M. Decreasing the Viscosity in CO2 Capture by Amino-Functionalized Ionic Liquids through the Formation of Intramolecular Hydrogen Bond. J. Phys. Chem. B. 2016, 120, 2807-2813. (52) Fukumoto, K.; Yoshizawa, M.; Ohno, H. Room Temperature Ionic Liquids from 20 Natural Amino Acids. J. Am. Chem. Soc. 2005, 127, 2398-2399. (53) Sakai, H.; Orihara, Y.; Kodashima, H.; Matsumura, A.; Ohkubo, T.; Tsuchiya, K.; Abe, M. Photoinduced Reversible Change of Fluid Viscosity. J. Am. Chem. Soc. 2005, 127, 1345413455. (54) Gutowski, K. E.; Maginn, E. J. Amine-Functionalized Task-Specific Ionic Liquids: A Mechanistic Explanation for the Dramatic Increase in Viscosity upon Complexation with CO2 from Molecular Simulation. J. Am. Chem. Soc. 2008, 130, 14690-14704. (55) Luo, X. Y.; Lv, X. Y.; Shi, G. L.; Meng, Q.; Li, H. M.; Wang, C. M. Designing Amino-Based Ionic Liquids for Improved Carbon Capture: One Amine Binds Two CO2. AIChE J. 2019, 65, 230-238.


20

Tuning the Capture of CO2 Through Entropic Effect Induced by

Recommend Documents