Controlled Gas Uptake in Metal-Organic Frameworks with Record Ammonia Sorption
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1 Supporting Information Controlled Gas Uptake in Metal-Organic Frameworks with Record Ammonia Sorption Adam J. Rieth and Mircea Dincă* Department of Chemistry, Massachusetts Institute of Technology, 77 Mass. Ave. Cambridge, Massachusetts, 02139, United States *Corresponding Author: Table of Contents Page 1. General Information S2 2. MOF Syntheses 3. Additional Ammonia Uptake Data S3 S4 4. Powder X-ray Diffraction Data S8 5. Nitrogen Isotherm Data S14 6. Electron Microscopy Data S21 7. InfraSORP Curve Fitting S23 8. References S30 S 1
2 Section S1: General Information. CuCl 2 *2H 2 O (99%, Alfa Aesar MnCl 2 *4H 2 O (98%, Strem Chemicals), CoCl 2 *6H 2 O (99.9%, Alfa Aesar), NiCl 2 *6H 2 O (Strem Chemicals), HCl (32-35%, BDH VWR Analytic) methanol (99.9%, VWR), N,N-dimethylformamide (99.8%, Millipore), ethanol (ACS grade, Mallinckrodt), and isopropanol (ACS grade, Macron) were used as received. Powder X-ray diffraction (PXRD) patterns were recorded with a Bruker Advance II diffractometer equipped with a θ/2θ Bragg-Brentano geometry and Ni-filtered CuKα radiation (Kα 1 = Å, Kα 2 = Å, Kα 1 / Kα 2 = 0.5). The tube voltage and current were 40 kv and 40 ma, respectively. Samples for PXRD were prepared by placing a thin layer of the appropriate material on a zero-background silicon crystal plate. Nitrogen adsorption isotherms were measured by a volumetric method using a Micromeritics ASAP 2020 gas sorption analyzer. A typical sample of ca. 40 mg of metalorganic framework, pre-activated at 100 C to remove all residual solvent, was transferred in an Ar filled glovebox to a pre-weighed analysis tube. The tube with sample inside was weighed again to determine the mass of the sample. The tube was capped with a Micromeritics TranSeal, brought out of the glovebox, and transferred to the analysis port of the gas sorption analyzer. Free space correction measurements were performed using ultra-high purity He gas (UHP grade 5, % pure). Nitrogen isotherms were measured using UHP grade Nitrogen. All nitrogen analyses were performed using a liquid nitrogen bath at 77 K. Oil-free vacuum pumps were used to prevent contamination of sample or feed gases. Ammonia adsorption isotherms were measured by a volumetric method using a Micromeritics ASAP 2020 gas sorption analyzer fitted with Kalrez seals. A typical sample of ca. 40 mg of metal-organic framework, pre-activated at 100 C to remove all residual solvent, was transferred in an Ar filled glovebox to a pre-weighed analysis tube. The tube with sample inside was weighed again to determine the mass of the sample. The tube was capped with a Micromeritics TranSeal, brought out of the glovebox, and transferred to the analysis port of the gas sorption analyzer. Free space correction measurements were performed using ultra-high purity He gas (UHP grade 5, % pure). Ammonia isotherms were measured using UHP grade ammonia. All ammonia analyses were performed using water baths held at constant temperature with a recirculating chiller. Oil-free vacuum pumps were used to prevent contamination of sample or feed gases. Ammonia breakthrough experiments were performed by Fraunhofer IWS, Dresden, Germany. A typical sample of approximately 60 mg of activated metal-organic framework was packed into the breakthrough apparatus and tested at an ammonia challenge concentration of 1000 ppm in N 2 with a flow rate of 140 ml/min at K. InfraSORP optical calorimetry measurements were performed by Fraunhofer IWS, Dresden, Germany. A typical sample of approximately 20 mg of activated metal-organic S 2
3 framework was loaded into the measurement chamber and tested at an ammonia challenge concentration of 1000 ppm in N 2 with a flow rate of 140 ml/min. Scanning electron microscope (SEM) images were acquired with a JEOL model 6010LA instrument. To mount samples for analysis, the dry powdered solids were sprinkled onto carbon tape. Elemental Analyses were performed by Robertson Microlit Laboratories, Ledgewood NJ. Section S2: MOF Syntheses. Synthesis of M 2 Cl 2 BBTA MOFs. Syntheses were as reported in the literature 1,2 with slight modifications in the case of Cu and Ni. In a typical synthesis, 100 mg H 2 BBTA (synthesized according to literature) 3 (0.624 mmol) was dissolved in 20 ml N,N -dimethylformamide (DMF) in a 100 ml jar. In a separate 100 ml jar, 1.25 mmol (2 eq.) metal chloride hydrate was dissolved in a solution of 20 ml methanol and 0.2 ml concentrated hydrochloric acid (HCl). The clear solutions were combined, capped, and heated to 65 C in an oven for 3 days. After this time, the reaction mixtures were removed from the oven and filtered to collect the solids. The solids were washed with DMF and methanol. Solvent exchange of DMF was carried out by Soxhlet extraction with methanol for approximately 48 hours. The materials were then activated under dynamic vacuum at 150 C for 24 hours. For Cu 2 Cl 2 BBTA, isopropanol was used in place of methanol and 2mL HCl was used. For Ni 2 Cl 2 BBTA, 8 ml HCl was used. Synthesis of M 2 Cl 2 BTDD MOFs. Syntheses were as reported in the literature 4,5 with slight modifications in the case of Cu. In a typical synthesis, 200 mg H 2 BTDD (synthesized according to literature) 6 (0.75 mmol) was dissolved in 200 ml N,N -dimethylformamide (DMF) in a 500 ml jar by stirring and heating to approximately 100 C. The clear solution was then cooled to room temperature. In a separate 500 ml jar, 1.5 mmol (2 eq.) metal chloride hydrate was dissolved in a solution of 200 ml ethanol and 4 ml concentrated hydrochloric acid. The clear solutions were combined, capped, and heated to 65 C in an oven for 10 days. After this time, the reaction mixtures were removed from the oven and filtered to collect the solids. The solids were washed with DMF and methanol. Solvent exchange of DMF was carried out by Soxhlet extraction with methanol for approximately 48 hours. The materials were then activated under dynamic vacuum at 100 C for 24 hours. For Cu 2 Cl 2 BTDD, isopropanol was used in place of ethanol, and 8mL HCl was used Elemental Analysis for BBTA MOFs Cu 2 Cl 2 BBTA Anal. C 20.21% H 1.34% N 23.06% Calc. C 20.23% H 0.57% N 23.60% Co 2 Cl 2 BBTA Anal. C 20.56% H 2.1% N 23.49% Calc. C 20.77% H 0.58% N 24.22% Ni 2 Cl 2 BBTA(0.3*DMF) Anal. C % H 1.57% N 24.62% Calc. C 22.49% H 1.12% N 23.96% S 3
4 Section S3: Additional Ammonia Uptake Data. NH 3 Adsorbed (mmol g -1 ) Sequential Cycles Co 2 Cl 2 BBTA Co 2 Cl 2 BTDD Figure S3.1. Uptake data for NH 3 adsorption at 1 bar, 293 K for activated samples of Co 2 Cl 2 BBTA and Co 2 Cl 2 BTDD. Materials were reactivated at 200 C under dynamic vacuum prior to each cycle. Bars represent iterative cycles on the same sample of each material. S 4
5 18 NH 3 Adsorbed (mmol g -1 ) P (bar) Figure S3.2. NH 3 adsorption (closed symbols) and desorption (open symbols) of an activated sample of Cu 2 Cl 2 BTDD at 298K. S 5
6 Wet Dry Ammonia C/C ο molecule NH 3 per metal Normalized Time (min/g) Figure S3.3. Ammonia breakthrough curves for activated samples of Cu 2 Cl 2 BBTA under wet (80% RH, pink) and dry (0% RH, orange) conditions. Dashed line indicates 1 molecule of NH 3 adsorbed per open coordination site. The challenge concentration C o was 1000 ppm with a flow rate of 140 ml min -1. Ammonia breakthrough measurements performed on Cu 2 Cl 2 BBTA, the bestperforming material in equilibrium measurements, indicate that the exceptional static capacity does not translate directly to dynamic capacity (Figure S3.3). The uptake at saturation under dry conditions was 7.52 mmol g -1, which exceeds HKUST-1 by more than 10%. 7 However, much of this capacity is available only after 5 ppm NH 3 is reached downstream. Under humid conditions, the capacity when the breakthrough criterion of 5 ppm is reached is equal to that measured in dry conditions. In both cases breakthrough occurs after approximately 0.9 molecules of ammonia are absorbed per open coordination site, confirming that direct metal binding is the primary driver for ammonia sorption at low concentration in these materials. S 6
7 NH 3 Adsorbed (mmol g -1 ) Co 2 Cl 2 BBTA Co 2 Cl 2 BTDD P (mbar) Figure S3.4. Low pressure ammonia isotherms for large-pore Co 2 Cl 2 BTDD (green diamonds) and small-pore Co 2 Cl 2 BBTA (blue triangles). S 7
8 Section S4: Powder X-ray Diffraction (PXRD) Data. NH 3 exposed Intensity Pristine Simulated θ / ο Figure S4.1. Powder x-ray diffraction patterns of as-synthesized Ni 2 Cl 2 BBTA (dark green), and after exposure to 1 bar NH 3 (light green), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BBTA 1 (black). S 8
9 Intensity NH 3 exposed Pristine Simulated θ / ο Figure S4.2. Powder x-ray diffraction patterns of as-synthesized Cu 2 Cl 2 BBTA (orange), and after exposure to 1 bar NH 3 (purple), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BBTA 1 (black). S 9
10 NH 3 exposed Intensity Pristine Simulated θ / ο Figure S4.3. Powder x-ray diffraction patterns of as-synthesized Cu 2 Cl 2 BTDD (orange), and after exposure to 1 bar NH 3 (purple), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BTDD 4 (black). S 10
11 1 mbar NH 3 exposed Intensity 1 bar NH 3 exposed Pristine θ / ο Simulated Figure S4.4. Powder x-ray diffraction patterns of as-synthesized Co 2 Cl 2 BBTA (blue), after exposure to 1 bar NH 3 (light blue), and after exposure to 1 mbar NH 3 (aquamarine), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BBTA 1 (black). S 11
12 Intensity Cold NH 3 exposed Pristine Simulated θ / ο Figure S4.5. Powder x-ray diffraction patterns of as-synthesized Co 2 Cl 2 BTDD (blue), and after exposure to 1 bar NH 3 at 263K (light blue), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BTDD 4 (black). S 12
13 Intensity Cold NH 3 exposed Pristine Simulated θ / ο Figure S4.6. Powder x-ray diffraction patterns of as-synthesized Ni 2 Cl 2 BTDD (dark green), and after exposure to 1 bar NH 3 at 263K (light green), along with a simulated pattern from the literature SC-XRD data for Mn 2 Cl 2 BTDD 4 (black). S 13
14 Section S5: Nitrogen Isotherm Data. Table S5.1. BET surface areas of measured MOFs before and after exposure to ammonia. BET areas were corrected by selecting the appropriate pressure region. 8 BET Area (m 2 g -1 ) Co 2 Cl 2 BBTA 1161 ± 1 Co 2 Cl 2 BBTA - Post 1 bar NH ± 1 Co 2 Cl 2 BBTA - Post 1 mbar NH ± 8 Ni 2 Cl 2 BBTA 1193 ± 4 Ni 2 Cl 2 BBTA Post 1 bar NH ± 4 Cu 2 Cl 2 BBTA 1205 ± 9 Cu 2 Cl 2 BBTA - Post 1 bar NH 3 19 ± 1 Cu 2 Cl 2 BTDD 1826 ± 23 Cu 2 Cl 2 BTDD - Post 1 bar NH 3 15 ± 2 Ni 2 Cl 2 BTDD 1827 ± 20 Ni 2 Cl 2 BTDD - Post 1 bar NH 3 263K 1737 ± 18 S 14
15 Pore Size Distribution (dv/dlog(w), cm 3 g -1 ) Co 2 Cl 2 BTDD 12 Co 2 Cl 2 BBTA Pore Width (nm) Figure S5.1. Barrett-Joyner-Halenda (BJH) 9 pore size distribution for pristine activated Co 2 Cl 2 BBTA (blue filled triangles) and Co 2 Cl 2 BTDD (blue empty diamonds) calculated using the Kruk-Jaroniec-Sayari 10 correction for hexagonal pores from the nitrogen isotherm data. S 15
16 400 N 2 adsorbed (cm 3 g -1 ) Ammonia-exposed Pristine P/P 0 Figure S5.2. N 2 adsorption isotherms for activated samples of pristine Ni 2 Cl 2 BBTA (dark green), and after exposure to 1 bar NH 3 (light green). S 16
17 N 2 adsorbed (cm 3 g -1 ) Pristine Ammonia-exposed P/P 0 Figure S5.3. N 2 adsorption isotherms for activated samples of pristine Cu 2 Cl 2 BBTA (orange), and after exposure to 1 bar NH 3 (purple). S 17
18 700 N 2 adsorbed (cm 3 g -1 ) Pristine Ammonia-exposed P/P 0 Figure S5.4. N 2 adsorption isotherms for activated samples of pristine Cu 2 Cl 2 BTDD (orange), and after exposure to 1 bar NH 3 (purple). S 18
19 N 2 adsorbed (cm 3 g -1 ) Pristine 1 mbar NH 3 exposed 1 bar NH 3 exposed P/P 0 Figure S5.5. N 2 adsorption isotherms for activated samples of pristine Co 2 Cl 2 BBTA (blue), after exposure to 1 bar NH 3 (light blue), and after exposure to 1 mbar NH 3 (aquamarine). S 19
20 N 2 adsorbed (cm 3 g -1 ) Pristine Ammonia-exposed P/P 0 Figure S5.6. N 2 adsorption isotherms for activated samples of pristine Ni 2 Cl 2 BTDD (dark green), and after exposure to 1 bar NH 3 at 263K (light green). S 20
21 Section S6: Electron Microscopy Data. Figure S6.1. Scanning Electron Microscope (SEM) image of an as-synthesized sample of Co 2 Cl 2 BTDD. S 21
22 Figure S6.2. SEM image of an as-synthesized sample of Co2Cl2BBTA. S22
23 Section S7: InfraSORP Curve Fitting. Curve fitting was performed in MATLAB R2016a. For kinetic modeling (Figures S7.1 and S7.2), the first 500 seconds of raw data was fit to the equation T = T o ((1-e -k1t )-(1-e - k2t )) Fitting the entirety of the data leads to variations in the rates with the same trend, though using all of the data qualitatively appears to artificially weight the curve fits towards thermal decay. (Figures S7.3 and S7.4). Due to lack of knowledge about the heat transfer characteristics, packing density and other factors, we do not attempt to derive absolute diffusivity constants from this data, however, we believe the method allows for an accurate comparison between the two materials. For more accurate integration of the data, raw data was fit to quadratic equations (Figures S7.5 and S7.6). Integration of the kinetic curves, followed by multiplication by the sample masses of 10.6 mg and 12.8 mg for Co 2 Cl 2 BTDD and Co 2 Cl 2 BBTA MOFs respectively provides an estimate for the energy transferred, and the energy transferred is a good estimate for the adsorbed amount of NH 3. If the fitted kinetic curves are used, the ratio of energy transferred to Co 2 Cl 2 BBTA vs. Co 2 Cl 2 BTDD is If the fitted quadratic curves are used, the ratio is S 23
24 Figure S7.1. Kinetic fit of the initial 500 seconds of InfraSORP data for Co 2 Cl 2 BBTA. Raw data in blue, fitted curve in red. The x axis is time in seconds, the y-axis is temperature change in degrees Celsius. Data fitted to the equation T = T o ((1-e -k1t )-(1-e - k2t )), k 1 = k 2 = T o = R 2 = S 24
25 Figure S7.2. Kinetic fit of the initial 500 seconds of InfraSORP data for Co 2 Cl 2 BTDD. Raw data in blue, fitted curve in red. The x axis is time in seconds, the y-axis is temperature change in degrees Celsius. Data fitted to the equation T = T o ((1-e -k1t )-(1-e - k2t )), k 1 = k 2 = T o = R 2 = S 25
26 Figure S7.3. Kinetic fit of all InfraSORP data for Co 2 Cl 2 BBTA. Raw data in blue, fitted curve in red. The x axis is time in seconds, the y-axis is temperature change in degrees Celsius. Data fitted to the equation T = T o ((1-e -k1t )-(1-e -k2t )) k 1 = k 2 = T o = R 2 = S 26
27 Figure S7.4. Kinetic fit of all InfraSORP data for Co 2 Cl 2 BTDD. Raw data in blue, fitted curve in red. The x axis is time in seconds, the y-axis is temperature change in degrees Celsius. Data fitted to the equation T = T o ((1-e -k1t )-(1-e -k2t )), k 1 = k 2 = T o = R 2 = S 27
28 Figure S7.5. Quadratic fit of InfraSORP data for Co 2 Cl 2 BBTA. Raw data in blue, fitted curve in red. f(x)= p 1 x 2 + p 2 x + p 3. p 1 = 1.368*10-7 p 2 = p 3 = R 2 = S 28
29 Figure S7.6. Quadratic fit of InfraSORP data for Co 2 Cl 2 BTDD. Raw data in blue, fitted curve in red. f(x)= p 1 x 2 + p 2 x + p 3. p 1 = 5.475*10-7 p 2 = p 3 = R 2 = S 29
30 References. (1) Liao, P.-Q.; Li, X.-Y.; Bai, J.; He, C.-T.; Zhou, D.-D.; Zhang, W.-X.; Zhang, J.-P.; Chen, X.-M. Chem. - A Eur. J. 2014, 20 (36), (2) Liao, P.-Q.; Chen, H.; Zhou, D.-D.; Liu, S.-Y.; He, C.-T.; Rui, Z.; Ji, H.; Zhang, J.-P.; Chen, X.-M. Energy Environ. Sci. 2015, 8 (3), (3) Hart, H.; Ok, D. J. Org. Chem. 1986, 51 (3), 979. (4) Rieth, A. J.; Tulchinsky, Y.; Dincă, M. J. Am. Chem. Soc. 2016, 138 (30), (5) Tulchinsky, Y.; Hendon, C. H.; Lomachenko, K. A.; Borfecchia, E.; Melot, B. C.; Hudson, M. R.; Tarver, J. D.; Korzyński, M. D.; Stubbs, A. W.; Kagan, J. J.; Lamberti, C.; Brown, C. M.; Dincă, M. J. Am. Chem. Soc. 2017, 139 (16), (6) Denysenko, D.; Grzywa, M.; Tonigold, M.; Streppel, B.; Krkljus, I.; Hirscher, M.; Mugnaioli, E.; Kolb, U.; Hanss, J.; Volkmer, D. Chem. - A Eur. J. 2011, 17 (6), (7) Katz, M. J.; Howarth, A. J.; Moghadam, P. Z.; DeCoste, J. B.; Snurr, R. Q.; Hupp, J. T.; Farha, O. K. Dalt. Trans. 2016, 45 (10), (8) Wang, T. C.; Bury, W.; Gómez-Gualdrón, D. A.; Vermeulen, N. A.; Mondloch, J. E.; Deria, P.; Zhang, K.; Moghadam, P. Z.; Sarjeant, A. A.; Snurr, R. Q.; Stoddart, J. F.; Hupp, J. T.; Farha, O. K. J. Am. Chem. Soc. 2015, 137 (10), (9) Barrett, E. P.; Joyner, L. G.; Halenda, P. P. J. Am. Chem. Soc. 1951, 73 (1), 373. (10) Kruk, M.; Jaroniec, M.; Sayari, A. Langmuir 1997, 13 (23), (11) Leistner, M.; Grählert, W.; Kaskel, S. Chemie Ing. Tech. 2013, 85 (5), 747. (12) Oschatz, M.; Leistner, M.; Nickel, W.; Kaskel, S. Langmuir 2015, 31 (13), (13) Sandra, F.; Klein, N.; Leistner, M.; Lohe, M. R.; Benusch, M.; Woellner, M.; Grothe, J.; Kaskel, S. Ind. Eng. Chem. Res. 2015, 54 (26), S 30
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